portland maine day trip itinerary

One Day In Portland Itinerary: What To Do In Maine’s Coolest City

Here’s my guide to spending one perfect day in Portland Maine.

In 24 hours, this Portland travel guide gives you a step by step itinerary for exploring all of Portland’s must see sites, attractions, and landmarks. It also clues you in on what to see, do, and eat in Portland, even besides lobster rolls!

Portland is the perfect place to start your coastal Maine road trip . Located on a peninsula jutting into Casco Bay, Portland is a rare metropolis in a state filled with small hamlets.

It’s a hip and laid back place that almost seems too cool for one of New England’s most beautiful towns . Portland has myriad cultural offerings and is a bastion of historical preservation.

The restored Old Port is a warren of cobbled streets, filled with vibrant Victorian buildings and buzzing farm to table eateries. On Exchange Street, you can nab anything from fudge to fine crafts.

Downtown, there’s a thriving art school, infusing the city streets with creative types. There are 24 commercial art galleries. Restaurants and coffee bars are filled with visual art. In June, the revived downtown hosts the Old Port Festival, described as “part freak show, part art festival, part fashion parade.”

In June, the revived downtown hosts the Old Port Festival, described as “part freak show, part art festival, part fashion parade.”

Portland is also a hot spot for restaurants, coffee shops, breweries, and entertainment. Did I mention breweries? Beer lovers will be happy to know that Portland has 18 breweries all its own. It’s the Craft Bew Capital of America.

Best of all? Portland is one best day trips from Boston , less than two hours away.

READ : Must See Landmarks in Boston

Best Things To Do and See in Portland Maine in One Day

Here’s how to make the most out of one day in Portland Maine.

1. Holy Donut

Start your day bright and early by fueling up at the Scarborough location of Holy Donut . Holy Donuts is a grass roots start up company. It was founded on a simple idea — making unique hand made donuts with Maine potatoes and quality ingredients.

Holy Donut is now a cult favorite. You can get any manner of donut. On my last visit, I sampled maple bacon, which was simply delicious. There are also vegan and gluten free options.

Right now, Holy Donut is only located on Park Street in Portland. But a new and convenient venue is opening in Portland’s Old Port in July 2021. Coming soon? Cake donuts and ice cream sandwich donuts.

When you’re fueled up, head to the iconic Portland Light Head. It’s open daily from sunrise to sunset.

Address : 398 US-1, Scarborough, ME

2. Portland Head Light

About 15 minutes from downtown Portland, Portland Head Light is one of the most world’s most photographed lighthouses. It’s a beacon of light perched on the dramatic craggy coast of Cape Elizabeth.

The pretty white stunner was built in 1791 and renovated in 1831. It’s the oldest lighthouse in Maine. The lighthouse had live in staff until 1989, when it was fully automated.

The cliff walk from the lighthouse offers stunning views and the wafting smell of the ocean.

There’s also a small onsite museum open during high season, which sits inside the former Keeper’s Quarters. It gives you an overview of the history of this famous lighthouse.

If hunger calls, there are some food trucks in the parking area where you can grab a lobster roll or taco.

Address : 12 Captain Strout Circle, Cape Elizabeth ME

3. Portland Museum of Art

Opened in 1983, Portland’s crown jewel and premiere art destination is the Portland Museum of Art . It’s an architectural masterpiece designed by I.M. Pei of Louvre fame. Its innovative architecture allowed curators to redefine the art viewing experience.

The small boutique museum is a little oasis of art in Portland’s Arts District. It has an impressive collection of late 19th and early 20th century art.

There are works by Andrew Wyeth, John Singer Sargent, Edward Hopper, Winslow Homer, and Marsden Hartley.

The museum also has a good cache of Impressionism works (Monet, Degas, Renoir) and hosts traveling international exhibits. The museum also promotes works by local Maine artists.

Address : 7 Congress Street, Portland ME

Hours : Thur, Sat & Sun from 10:00 am to 6:00 pm, Fri from 10:00 to 8:00 pm. On Friday, there’s free admission for all

Entry fee : $25

4. Cathedral of the Immaculate Conception

In 1866, Portland’s Great Fire destroyed the first iteration of Portland’s cathedral. But it was replaced with a beautiful 200 feet tall Neo-Gothic brick structure.

The twin tours are somewhat reminiscent of Strasbourg Cathedral, a famous landmark in France . The cathedral is on the National Register of Historic Places.

The Roman Catholic church serves as the diocese in Portland. Inside, you’ll find stained glass windows from Munich, seven imposing pillars on each side of the nave, Gothic arches, and a lovely organ.

Address : 307 Congress St, Portland, ME

4. Lunch in the Old Port

It’s lunchtime! The classic Portland lunch is a lobster roll at the Portland Lobster Co .

At this casual seaside joint, you can sit under umbrellas and admire the Old Port. Their seafood is locally sourced and mostly organic. Even their straws are biodegradable.

Another good option on Middle Street for lunch at Eventide Oyster Co . Servers will shuck oysters caught that morning right before your eyes, while you’re waiting for the requisite lobster roll.

If seafood isn’t your thing, across the street is Duckfat .

The restaurant serves up European-style sandwiches and crispy pomme frittes. These hand cut fries are fried in, as its name suggests, duck fat. They come with a selection of fancy dipping sauces.

As an alternative to a specific place for lunch, you may want to take a 2-3 hour food tour in the old Port . Or go on a 3 hour food truck tour by bike .

As an alternative to a specific place for lunch, you may want to take a 2-3 hour food tour in the old Port or a 2.5 hour seafood tour . Or, for even more fun, go on a 3 hour food truck tour by bike .

5. Explore the Old Port

After lunch, explore ehe charming Old Port. It’s a picturesque historic neighborhood with a movie set feel. With its cobblestone lanes and photogenic harbor, the Old Port district is dose of urban New England charm in a state of bucolic pleasures.

You may want to book a 2 hour history walking tour in the Old Port.

Start on Commericial Street, the main drag, and work your way inward. The Old Port is known for its cobblestone streets, 19th century brick buildings, and fishing piers. The Old Port is also a hive of activity.

From posh to funky, you’ll find all the best boutiques, galleries, restaurants, and bars in Portland. It’s a great place to dine and bar hop, though in the summer you’ll have tourists.

If you hate malls, the Old Port is a wonderful place to shop. Everything is unique and for sale in quaint boutique shops.

Zane is my favorite women’s clothing store in Portland. Another popular designer concept shop is Judith , though I personally found the clothing to be rather unapproachable and too formal.

Chefs should head to LeRoux Kitchen with a slew of kitchen gadgets and an entire floor dedicated to Le Creuset cookware.

Or try Stonewall Kitchen , a gold mine of ingredients. The Salt Cellar is super cute with a huge selection of culinary and spa salts.

For exquisite artisan pottery or glass art, try Simon Pierce or Edgecomb Potters .

If you need a snack, head to Beal Ice Cream Shop or Old Port Candy Co . Bibliphiles should also pop into Longfellow Books .

6. Portland Schooner Company

If you have time, in the late afternoon, take a 2 hour boat ride on Casco Bay. Portland Schooner Co has three early 1900s schooners on the National Register of Historic Places.

You’ll have a different view of Portland and a deep breath of sea air.

Address : 56 Commercial Street, Maine State Pier, Portland, ME

6. Pre-Dinner Cocktails

No trip to Maine would be complete without trying the hometown craft brews, so head to Novare Res Bier Care or Allagash Beer . Click here for a definitive guide to the best breweries in Portland.

Alternatively, sample a luscious Italian wine at Via Vecchio on Dana Street. If you’re there for happy hour, you’ll get a free charcuterie plate.

With local fresh seafood on its doorstep, a popular farm-to-table vibe, and a smattering of creative contemporary restaurants, Portland Maine is officially a foodie haven.

I loved Solo Italiano on Commercial Street best. The restaurant serves up creative northern Italian dishes. The pasta is delicious and hand crafted in house.

Alternatively, head to Fore Street . This restaurant is regularly in the running for accolades. It features food that’s foraged, farmed, and fished locally and is set amid an intimate open air kitchen. Get the mussels, which are the best on the coast of Maine.

Two other Portland restaurants made the New York Time’s list of best restaurants in the US in 2022 — Leeward and Twelve.

Leeward serves up pasta dishes and seafood and is a James Beard finalist. Twelve has a beautiful minimalist decor and is housed in a historic brick building on the waterfront. There’s a prix fixe and a la carte menu and extensive wine list.

If you’re a connoisseur of craft beer, you may want to take a 2 hour craft breweries tour as well.

8. City Hall & Merrill Auditorium

If you opted for an early dinner, take in a performance at Merrill Auditorium in City Hall.

Portland’s current City Hall was completed in 1912 in the Renaissance revival style. The three story, horseshoe shape building features a mansard roof. As the seat of Portland’s government, the building houses the city’s offices. It’s also home to Merrill Auditorium, a 3,000 seat venue.

Merrill Auditorium is the site of Portland’s performing arts scene. It’s an elegant restored concert hall, which houses the world famous Kotzschmar Memorial Organ.

The venue hosts concerts by the Portland Symphony Orchestra, touring national theater companies, dance companies, and music acts. The Portland Opera Repertory also uses Merrill for full scale productions and performances.

Address : 20 Myrtle St, Portland, ME

Tips For Spending One Day in Portland Maine

Here are some must know tips for having an efficient day in Portland.

1. How To Get To Portland

Portland is home to Maine’s largest airport, Portland International Airport. So you can fly right into Portland.

You can also fly into Boston’s Logan Airport, which is a 1:45 drive from Portland.

If you’re already in the city, Portland is one of the best day trips from Boston . You can take the train from North Station in Boston to Portland Transportation Center. From the station, it’s a 40 minute walk, 10 minute bus ride, or 5 minute taxi ride.

2. How To Get Around Portland

Portland is a compact and walkable city. I walked everywhere in Portland.

But there are many other fun ways to explore the city by ferry, bus, boat, or bike. You can:

• take a 3 hour bike tour around Portland
• take a 3 hour street art bike tour
• take a 3 hour tour to the lighthouses
• take a lunch cruise in downtown Portland
• take a nighttime dinner cruise
• or take a sightseeing tour on a vintage fire truck

3. Where To Stay In Portland

Portland is filled with fantastic hotels. Here are the top four choices, to my mind.

The Blind Tiger is a cool boutique hotel in a 19th century mansion in the Old Port. It’s a luxurious place with bright colors and a private rooftop deck.

The Press Hotel is a cool hotel where the rooms look like writers’ desks. There are typewriters in the lobby and old new copy blown up on the wall.

The Best Bower is a tiny boutique hotel in the city’s restaurant-friendly East End. It’s housed in a beautifully restored craftsman building.

The Francis is Portland’s newest boutique hotel. It’s housed in a restored 19th century building. There’s custom furniture and art in the rooms.

4. When To Visit Portland Maine

The best time to visit Portland is June through October. You’ll get reliable good weather and can enjoy the outdoor activities. Winter begins in mid November is very chilly.

5. More Than One Day In Portland?

There are plenty of other interesting things to do if you have more than one day in Portland.

1. Eastern Promenade

Portland has some excellent green spaces. Designed in 1905 by the minds beyond Central Park, Portland’s beloved Eastern Promenade offers stunning vistas of Casco Bay.

The promenade is Portland’s playground. It’s a 68.2 acre historic public park. There’s plenty of walking and running trails and picnic areas.

Park your car along this stretch of green and walk along the hilltop. From there, you can admire Victorian mansions and watch ferries carrying commuters to offshore islands.

The active among you should rent a bike at CycleMania in East Bayside and complete the 3.6 mile Back Cove Trail. The Front Room will revitalize the famished. If it’s caffeine you need, head to the Hilltop Coffee Shop.

2. Portland Break Light, Known as Bug Light

If you want a lighthouse all to yourself, head to Bug Light . Its official name is the Portland Breakwater Lighthouse, but the locals don’t call it that. If you’ve started your day early, you could stop here on your way from Portland Head Light into the city center.

Bug Light is a unique little beauty. It’s a rare lighthouse with decorative Corinthian columns, taking a cue from classical Greece. It’s perched on the cusp of Portland Harbor and gives you sweeping views of Portland’s cityscape.

Bug Light Park provides 9 acres of meticulously maintained and manicured parkland. You can picnic, hike, or kite.

Are you obsessed with lighthouses? If so, you want a tour of Portland and all 3 lighthouses nearby, you can book this 2 hour tour with a local .

Address : S Portland Greenbelt Parkway, South Portland ME

3. Hiking Trails

Portland also has plenty of outdoor hiking trails for nature lovers. An hour from Portland is the Burnt Meadow Mountain Trail, which is a 3.6 mile trail strewn with wildflowers.

To land on a beach, hike the meandering 3.8 trail from Morse Mountain to Seawall Beach.

Just 30 minutes from Portland is Bradbury Mountain State Park, with an easy 1.9 mile trek on the Tote Road Loop.

4. Home of Henry Wadsworth Longfellow

If you like to admire Victorian mansions, head to West Portland. Make your way to the historic home of poet Henry Wadsworth Longfellow . It’s a three story brick landmark, a fine example of Colonial architecture and the oldest building on the peninsula.

Longfellow penned many of his poems right from this home. Built in 1785, the Longfellow House is now the home of the state’s historical society.

Once inside, you can step back into the daily life of the most famous author of the day. There is original period furniture and artifacts. Behind the house is the Longfellow Garden. It’s a quiet oasis in Downtown Portland that’s free to visit.

Address : 489 Congress St, Portland, ME

I hope you’ve enjoyed my one day itinerary for Portland. You may enjoy these other New England travel guides and resources:

• 3 Days in Boston Itinerary
• 1 Day In Cambridge Itinerary
• 7-10 Day Itinerary for Vermont
• 10 Day Itinerary for New Hampshire
• 25 Most Beautiful Towns in New England
• 10 Day Itinerary for Coastal Maine
• Fall Foliage Road Trip in New England
• 3 Day Itinerary for Boston
• Walking the Freedom Trail in Boston
• What To Do In the Berkshires
• Places To Visit In Massachusetts

If you’d like to spend 1 day in Portland Maine, pin it for later.

1 thought on “One Day In Portland Itinerary: What To Do In Maine’s Coolest City”

We recently stumbled across your Portland, Maine, article and enjoyed reading it. There is certainly no shortage of things for visitors and locals alike to explore.

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Last Updated on March 13, 2023 by Leslie Livingston

Adventuring Dreamers

Perfect Day Trip to Portland, Maine: The Best 1-Day Itinerary

A One Day Itinerary for Portland, Maine: History, Food, and Lighthouses

Planning a day trip to Portland, Maine? Here’s the perfect one-day Portland itinerary covering the downtown area, history, and lighthouses.

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A day trip to Portland, Maine, is an ideal getaway for anyone on the East Coast looking to have a quick escape to a beautiful, historic New England town. Just a couple of hours from Boston and a few more hours away from New York City , this town is filled with adventures just waiting to happen.

There’s no place quite like Portland, Maine. 

I recently discovered this when I planned a quick trip over to the coastal city by happenstance. A few months ago, I found out that a Canadian musician my mom loves was going on tour and would be visiting limited U.S. cities. The only date and city that made sense for us to go was in Portland in October . So, on a whim, I orchestrated a little family vacation for my mom, sister, and me to see the show.

It was just a quick little trip, with the primary motive being to see the concert at Merrill Auditorium. But since none of us had been to Maine before, we decided to stick around for just one day and explore the town. I am so glad we did.

In just a single day, you can learn about the history of one of the U.S.’s oldest cities. Relish the culinary delights of Portland’s downtown restaurants. And admire the charming lighthouses that pepper the landscape.

Portland is one of the most unique towns in the U.S., and even if you’ve only got a day to explore, it’s absolutely worth the visit.

Table of Contents:

Day Trip to Portland, Maine Itinerary Getting to Portland, Maine How To Get Around in Portland, Maine Where To Stay in Portland, Maine Spending More Than One Day in Portland, Maine? Visiting Portland, Maine: FAQ Final Thoughts on a Day Trip to Portland, Maine

Day Trip to Portland, Maine Itinerary

This day trip to Portland, Maine, itinerary covers everything you need to know to enjoy the absolute best trip to this beautiful New England town. In this guide, we’ll go over all the details from what to do, what to eat, and how to get from place to place. Let’s get into it!

When To Arrive in Portland

This day trip to Portland, Maine, itinerary was built with the intention that you have a full day to spend in town. 

I’ve curated a list of activities starting first thing in the morning and going deep into the night. 

To use this Portland day trip itinerary to its fullest extent, try to arrive in Portland no later than 9 a.m. This will give you enough time to grab breakfast and then head over to your first activity.

Morning in Portland

Coffee & breakfast.

Is there a better way to begin a day of exploration than with a delicious coffee and a delectable donut? Me thinks not. Begin your day on the right note by grabbing a cup of coffee and savoring a legendary donut from The Holy Donut .

The café has been crafting unique potato donuts — yes, made out of potatoes! — from scratch every morning since 2010. The Holy Donut opens bright and early at 7 a.m., so it’s a superb choice for any early birds looking to get a sugar rush and a little extra exploration in before the day officially begins. 

For the rest of us who like to sleep in (hello, it’s me), the café is conveniently located on Commerical Street, just a couple of blocks away from the first activity on our day trip to Portland itinerary. So, feel free to grab a moist Apple Cinamon or Fresh Lemon donut as late as 9 a.m. before trotting down the street to start your adventure.

The Holy Donut services over 35 original flavors to choose from, including eight vegan options , like Old Fashioned, Toasted Coconut, and Cinnamon Sugar!

The Holy Donut: 177 Commercial St. Portland, ME 04102

Walk Through Time in Portland Tour

We started our morning in Portland with a guided walking tour through Portland’s downtown area. It was a great way to get familiar with the area, learn about the history of the port, and gain some insider tips on the best restaurants and speakeasies in town. 

We did the Walk Through Time in Portland Tour , which took us through the Old Port, around Downtown, and throughout the waterfront areas. Even though our tour guide, James, was “from away” (Portland’s term for anyone who doesn’t have family dating back three generations in the state), he migrated to Portland over 30 years ago and had plenty of local tips to offer our group. 

We learned a lot about the history of Portland and even got an exclusive VIP peak into the historic Customs Building!

The tour starts at 10 a.m. and lasts about 2.5 hours, ending just in time for lunch in the historic downtown Portland area.

Click here to read a full review of my experience with the Walk Through Time in Portland Tour.

Afternoon in Portland

As a vegetarian, I can’t tell you which restaurant serves the best lobster rolls. Luckily for you, Portland is frequently named one of the top foodie places in the country, and you probably can’t go wrong with any restaurant downtown when it comes to fresh seafood. 

However, if you’re a veg-head like me and are looking for vegetarian and vegan options , I recommend grabbing a bite at Green Elephant .

Located on the corner of Congress Street and High Street, Green Elephant serves exquisite pan-Asain cuisine, all vegan or vegetarian. Packed with tons of veggies and flavor, every dish here is absolutely delightful. I recommend trying the spring rolls or pad thai.

Green Elephant: 608 Congress St, Portland, ME 04101

Portland Museum of Art

If you dined at Green Elephant, the restaurant will put you right across the street from the Portland Museum of Art , aka the PMA.

The PMA boasts an extensive collection, housing over 18,000 pieces of art.

Within this collection, you’ll encounter familiar names like Andy Warhol and Claude Monet, as well as lesser-known artists such as Yasuo Kuniyoshi and Eliot Porter.

Wandering through the exhibition halls of this magnificent structure can easily consume hours of your time. But to make the most of your day trip to Portland, I recommend limiting yourself to one to two hours, so you have time to complete the rest of the itinerary before the day is over.

To make the most of your visit, consider focusing on the specific works that genuinely captivate you.

Admission for adults is priced at $18, while individuals aged 21 and under can enjoy free entry.

Portland Museum of Art: 7 Congress Sq, Portland, ME 04101

Adventurer’s Note: The museum offers free admission to everyone on Fridays from 4-8 p.m. So, if your day trip falls on a Friday, I recommend adjusting this itinerary a bit to take advantage of Free Fridays.

Wadsworth-Longfellow House and Longfellow Bookstore

Only a 5-minute walk from the PMA is the historic Wadsworth-Longfellow House and Longfellow Bookstore .

This old brick house stands out from the surrounding industrial buildings of newer Portland and is a testament to the past. The house is the former 19th-century residence of the renowned poet and intellectual Henry Wadsworth-Longfellow. And it’s been a landmark of the Maine Historical Society for over a century. 

Admission is priced at $15 per person, and self-guided tours are available until 3:30 p.m. Tuesday to Saturday. Advanced booking is necessary.

If you’re doing both the PMA and the Wadsworth-Longfellow House, I recommend only spending an hour at PMA and arriving at the Wadsworth-Longfellow House by 2:30. This will give you enough time to explore both museums before the cut-off time.

Even if you opt not to explore the Wadsworth-Longfellow House museum during your day in Portland, Maine, be sure to take a peek inside the bookstore.

Wadsworth-Longfellow House and Longfellow Bookstore: 489 Congress St, Portland, ME 04101

Adventurer’s Note: If you prefer, guided tours are exclusively offered on weekdays at 1 p.m. and 2 p.m.

Shopping on Exchange Street

Exploring the Henry Wadsworth-Longfellow House will put you about a 5-minute walk from Exchange Street and the rest of Portland’s downtown shopping area. I highly recommend setting aside some time during your day trip to explore the many artisan shops that dot the cobblestone streets.

From unique boutiques to metaphysical shops to bookstores to artists’ studios, the shopping district has something for everyone.

My favorite shop was The Maine Souvenir Shop — which is not your average souvenir store by far. They carry an extensive inventory of typical souvenir items like magnets, stickers, and t-shirts, but with a twist. Most of their stuff is created by local artists, including the shop owner, and has its own fun personality. It’s very different from your typical souvenir shops filled with mass-produced junk.

The Maine Souvenir Shop: 2 Exchange St, Portland, ME 04101

Self-Guided Lighthouse Tour

More than the shopping or the food, Portland, Maine, is known for its historic lighthouses. I saved visiting the lighthouse for the afternoon because, if you time it right, you’ll be able to catch stunning views of the lighthouses at sunset.  

You have two options when it comes to visiting the lighthouses — guided tours or self-guided tours. I’d recommend saving guided lighthouse tours for a more extended trip. But for just a quick day trip to Portland, I’d recommend doing a self-guided tour so you can have complete control over your schedule.

Start With the Portland Head Light

George Washington ordered the creation of the Portland Head Light in 1791, and Revolutionary War hero Marquis de Lafayette dedicated it. It’s Maine’s oldest lighthouse and Portland’s most famous lighthouse.

The lighthouse remains operational to this day. A glance over the edge shows why — below the beautiful lighthouse lays a perilous bed of rocks waiting for a misguided ship.

The lighthouse is at Fort Williams Park, a 90-acre park on the edge of the Atlantic Ocean. Next to the lighthouse tower is a charming keeper’s house, part of which has been transformed into a museum dedicated to the lighthouse’s history. The park also offers picnic areas and hiking trails.

For the most breathtaking views of the lighthouse, be sure to follow the cliff-side trail. It’s a short 5-minute walk that will take you to vista views of the lighthouse and the rugged coastline.

The Portland Head Light is a terrific first stop on your self-guided lighthouse tour because, from the base of the lighthouse, you’ll be able to view all the lighthouses in the area:

• Spring Point Ledge Light , built in 1897, sits to the North. 
• Ram Island Ledge Light , built in 1905 and now powered with solar energy, sits directly in front of Portland Head Light. 
• Halfway Rock Light Station , built in 1871, is beyond Ram Island, approximately 10 miles out, and visible on clear days. 
• Cape Elizabeth Light , built in 1874, is to the South.

These five lighthouses make up all the major lighthouses in the Portland area. Since you can see all lighthouses from the Portland Head Light, you now have a choice — you can either hang out at Fort Williams Park and enjoy the amenities or leave to explore the other lighthouses listed above in person.

Portland Head Light: Cape Elizabeth, ME 04107

Spring Point Ledge Light

Even if you decide to spend most of your time at the Portland Head Light, I recommend at least making the drive over to the Spring Point Ledge Light . It’s only about 15 minutes away by car.

This lighthouse is much smaller than the Head Light, but the views here are simply incredible.

Spring Point Ledge Lighthouse stands as the sole caisson-style light station — a lighthouse built on a metal or concrete structure — in the United States accessible to visitors on foot. 

The walk involves balancing — and occasionally jumping — across a narrow stone path. It’s a quick walk with breathtaking views. And it’s definitely worth the trip.

Spring Point Ledge Light: 2 Fort Rd, South Portland, ME 04106

Evening in Portland

Perhaps it’s the fact that I’m from the Southwest originally and lived in Phoenix , Arizona, for 10 years, but there’s something incredibly intriguing about eating Mexican food in the United States’ most northeastern state. 

Taco Escobarr is a vibrant tavern boasting a fantastic selection of tacos and margaritas, creating a delightful atmosphere that serves as an ideal launching point for your evening. 

At this point, there are only a few more hours left in this one-day Portland itinerary, and there’s a whole evening planned. So be sure to fuel up on tacos and chips and salsa and get ready to party in the Portland style.

Taco Escobarr: 548 Congress St, Portland, ME 04101

Grab a Pint at a Local Brewery

Portland, which is home to 70+ local breweries, is the craft beer capital of the United States.

In fact, Maine stands out with one of the highest brewery densities per capita in the country. It’s an ironic fact, considering that Maine was the birthplace of prohibition, banning alcohol decades earlier than the rest of the U.S. in 1851.

Portland, Maine, boasts some of the finest craft beer in the entire country. So, if you’re a fan of craft beer, it would almost be a crime to skip the local breweries in Portland.

Head over to Industrial Way, where you’ll discover a cluster of five breweries conveniently situated within walking distance: 

• Allagash Brewing Company
• Foundation Brewing Company
• Austin Street Brewery
• Battery Steele Brewing
• Definitive Brewing Company

It’s the perfect place to hop from one brewery to another, sampling a diverse array of offerings from Portland’s top breweries.

Please remember to drink responsibly!

Sneak Into a Speakeasy

Remember how I said that Maine was the first state to introduce prohibition? Well, what do we now know happens when the government tries to get in between people and their liquor? They go underground!

Nowadays, speakeasies are a legal and fun way to pay tribute to partiers of generations past. Portland does a great job of remembering the history of its illegal speakeasies by being host to a group of secret clubs hidden throughout the downtown area.

Blyth & Burrows

On Exchange Street, you’ll find the front entrance of Blyth & Burrows , a delightful cocktail bar spanning two levels in an old brick building.

This establishment prides itself on an array of signature cocktails, complemented by a “small plates” menu, perfect for those seeking delectable nibbles.

But this dignified restaurant and lounge is just the front to the speakeasy in the back.

Inside the cocktail lounge is a bookcase that conceals a secret staircase. 

This secret bar in the back is smaller and much less formal. It has a more intimate and sort of “unfinished” vibe, kind of like what a speakeasy from days of old would be like. And just like the front of the house, the speakeasy in the back also boasts a full bar.

The establishment’s name, Blyth & Burrows, pays homage to Commander Blythe of the HMS Boxer and Lieutenant Burrows of the USS Enterprise. These brave individuals lost their lives in a naval battle off the coast of Maine during the War of 1812, and they rest side by side in Eastern Cemetery in Portland. A special mural at the rear of the cocktail bar serves as a tribute to this historic battle.

Blyth & Burrows: 26 Exchange St, Portland, ME 04101

Lincolns Speakeasy

Lincolns Speakeasy offers the best deals on drinks in town — that is if you can find the entrance.

Located down the stairwell of Market Street Eats, Lincolns gets its name from how everything is only $5. It’s cash only though, so make sure to make a pitstop at an ATM on your way over.

The atmosphere here is friendly and warm. It’s a great place to hang out for the evening while sipping on some of the most affordable cocktails in town.

Market Street Eats: 36 Market Street Main Floor, 36 Market St 3rd Floor, Portland, ME 04101

This speakeasy gets its name because it’s located on the top floor of a pizza pie restaurant. Pie North . Get it?

Pie North is an 80s arcade-themed speakeasy decorated to the brim with nostalgia. Infusing retro-inspired musical decor with classic arcade games, they’ve crafted a distinct and entertaining ambiance that’s truly one-of-a-kind in Portland.

Pat’s Pizza: 30 Market St, Portland, ME 04101

Getting to Portland, Maine

If you’re doing a day trip to Portland, Maine, you’re probably already close by or are visiting Portland as part of a longer New England road trip. Either way, you’ve got options on how to get into the city.

Driving to Portland, Maine

The journey to Portland, Maine, is an easy day trip from Boston, Massachusetts, since the towns are only about two hours away from each other.

The scenic drive from Boston to Portland is a picturesque journey covering 107 miles. As you follow the coastline, you’ll be treated to breathtaking vistas of the ocean and rugged cliffs.

A day trip to Portland is an essential excursion for any Boston resident seeking a break from the city and a taste of New England’s coastal allure. It’s equally appealing for visitors to Boston who wish to explore another enchanting New England city!

It’s also worth the drive to Portland from other areas of the Northeast. For instance, I visited Portland from Manhattan to see a concert at Merrill Auditorium. Although NYC is a little far for a day trip, since it’s only a five-hour drive from the Big Apple, Portland was the perfect little weekend getaway.

Train to Portland, Maine

The train is another excellent option for traveling to Portland. Opting for the Amtrak Downeaster offers an excellent choice for travelers looking to relax and savor the picturesque landscapes.

This train journey spans approximately 2.5 hours from Boston, with ticket prices ranging from $3 to $30.

As the train meanders along the route, you’ll be treated to a changing panorama, from sandy beaches to expansive, rolling green fields. And it’s an absolute dream if you travel in the fall when the leaves are changing color.

The ride itself is both comfortable and hassle-free, ensuring passengers can unwind and relish the journey with ease and peace of mind.

Flying to Portland, Maine

If driving or training are not feasible options, then flying into Portland might be your best bet.

All major airlines offer flights to Portland. The city’s primary airport, Portland International Jetport (PWM), is a mere couple of miles from the city center. 

To reach your destination within the city, you have several transportation options. Taxis, ride-sharing services, rental cars, and the METRO bus system are readily available. 

The Greater Portland Transit District METRO operates Route #5, providing bus service from the airport to downtown Portland.

Alternatively, if you’re flying from overseas, you might discover better flight options through Boston Logan International (BOS). However, then, you’ll either need to drive or take a train from Boston to Portland.

How To Get Around in Portland, Maine

The downtown Portland area is very walkable. In fact, once you’ve parked your car, you won’t need it again until you’re ready to leave the Old Port area. 

But, if you want to see the lighthouses or other notable attractions outside of the city center, then you’ll also need some sort of transportation on wheels. This could either mean a car or public transportation.

Here are some transportation options while in Portland, Maine:

While the city center is very walkable, you’ll need some other mode of transportation to get you to farther attractions like the lighthouses. 

If you’re up for the adventure, Portland boasts numerous well-marked bike lanes in and around the city. Many hotels offer bike rentals for day use, and there are public bikes for rent as well, making it easy to pedal your way around and see the sights. 

However, keep in mind that biking is a slower mode of transportation. So, if you choose this option, you might need to adjust your itinerary to give you ample time to arrive at each destination. 

Public Transportation

Portland offers a convenient bus service, providing reliable access across the entire city. 

Since your stay in Portland is limited to a single day, the most straightforward way to pay for rides is with cash. So having some loose change on hand is advisable. Each journey typically falls within the range of $1 to $4, and you’ll need to have the exact amount.

It’s easy to get around town on the bus — or METRO as they call it — and some locals don’t even have cars. In fact, our walking tour guide mentioned how he’s been living in Portland without a car since 2007 and just takes the bus anywhere he needs to go.

Like any popular city or town, you’ve always got the option of using Uber or Lyft. A trip with a ride-share service is obviously going to be pricier than a bus ticket. But it can also be quicker and more convenient, especially since you’ve only got a day in town. It’s also less than the cost of a rental car.

If you’re planning on drinking and are not staying somewhere within walking distance of the brewery, then ridesharing is also a responsible decision that will keep you and those around you safe.

The easiest way to get around Portland is by car. Navigating in Portland is very straightforward, and parking is easy peasy, albeit a bit pricey, depending on where you go.

You’ve got lots of options for parking, from paid lots to on-street parking to garages. We opted for metered parking because it was the most affordable at only $2.50 per hour. We tried a parking lot first, but it was a little on the pricier side — $15 for the first hour and $5 per hour after that!

Adventurer’s Note: On-street parking in Portland is complimentary from 6 p.m. until 9 a.m., Monday through Saturday, as well as all day on Sundays and major holidays. Check out the PassportParking App to ensure a hassle-free parking experience.

Where To Stay in Portland, Maine

The best place to stay in Portland depends on the mode of transportation you’re using to get around town. 

Portland hotels are pretty pricey. In fact, a survey by Cheaphotels.com 1 showed that Portland was the second most expensive city for hotels in the United States, following behind Nantucket, Massachusetts. And when we did our tour through the Customs House, the gentleman guiding the tour joked that hotels in the area were so expensive that he could probably get $250 a night by renting out the 12-square-foot safe hidden in the building.

Because of how expensive Portland hotels are, I recommend staying in an Airbnb or VRBO instead. 

The Cozy BnB

We stayed in a lovely Airbnb in Scarborough hosted by Steven. The Airbnb name is Rustic Suite near downtown Portland and Beaches , and I highly recommend it. The BnB is exactly as it’s listed on the site. It’s incredibly cozy, very clean, and comfortable.

The place is honestly such a vibe. It’s a bit of an odd layout as a studio apartment with the master bed in the front and then an add-on room in the back that creates a family room/TV space. There’s a futon by the TV for a second bed. And there’s a super fun loft area with two more twin beds overlooking the family room.

We were much more comfortable here than we would have been in a hotel, and it allowed us to see the surrounding neighborhood of one of the U.S.’s oldest towns. 

The stay was only a 10-minute drive from downtown. 

And it’s pet-friendly. My husband stayed at home with our dogs on this particular trip, but I know I’ll be showing him Portland sometime soon, and this place will be the first place I try to book — especially since I know we can bring our dogs here.

If vacation rentals aren’t your style or you’d like to stay closer to the downtown area, here are a few highly recommended hotels in Portland, Maine:

Luxury: The Press Hotel

For a combination of history and luxury, enjoy a stay at the Press Hotel . 

The building has been in Portland for over a century, and the name of the hotel comes from the Portland Press Herald newspaper that used to live there. 

Thirteen years ago, the newspaper moved to another building, and the old office space was turned into an independent luxury boutique hotel that is an esteemed member of the Autograph Collection.

Nestled in the heart of downtown Portland, this pet-friendly 4-star hotel offers rooms adorned with refined details and distinctive features, including a rotating art gallery. 

While it might be on the pricier side, a single-night stay here will ensure that your day trip to Portland is nothing short of unforgettable.

Mid-range: The West End Inn

Consider the charming West End Inn for a mid-range lodging option. Located in the downtown area, it offers convenient access to prominent attractions, including the Victorian Mansion, just a half-mile away. This delightful inn enhances your stay with a delectable breakfast menu and entertaining themed dinner nights.

Budget: Holiday Inn Portland-by the Bay

Holiday Inn Portland-by the Bay may be more budget-friendly, but it doesn’t skimp on the impressive views, hospitable staff, and valuable amenities like parking and e-bikes! Besides, who needs luxury living when you’ve got an entire city to explore?!

Hostel: Black Elephant Hostel

Colorful, funky, and fun, the Black Elephant Hostel is everything one could wish for when it comes to budget accommodations. 

Black Elephant Hostel is the first and only hostel in Portland, Maine, and it was created with the mission of uniting a melting pot of people and cultures and bringing hostel culture to this historic New England town. 

Spending More Than One Day in Portland, Maine?

Got more time to spend in Portland, Maine? Here are a few more things to do in Portland to fill up the rest of your itinerary:

Victoria Mansion

The Victoria Mansion , also known as the Morse-Libby House, was built between 1858 and 1860 as a summer residence for Ruggles Sylvester Morse and his wife, Olive.

Designed by the architect Henry Austin of New Haven, CT, this remarkable summer home is widely acclaimed as one of the finest exemplars of the Italian Villa style in America.

In 1940, the house was rescued from an uncertain future and has served as a public museum since 1941. Today, Victoria Mansion proudly preserves over 90% of the original interiors, including almost all of the original wall paintings by the Italian-born artist Giuseppe Guidicini.

Victoria Mansion: 109 Danforth St, Portland, ME 04101

Portland Tall Ship Cruise on Casco Bay

Embark on a unique voyage alongside the Portland coast while relishing a leisurely journey upon a traditional, locally crafted dinghy during this Portland Tall Ship Cruise on Casco Bay . 

The adventure will begin near the Maine State Pier, where you’ll board the ship and wait for the sails to unfurl and the wind to carry you across the water. You’re even invited to partake in the experience by helping raise the sails or taking a turn at the ship’s wheel. 

This family-friendly excursion caters to both children and adults, providing an uncommon outlook on Portland that most visitors never encounter.

Portland, Maine Black History Walking Tour

On this walking tour of Maine’s Black History , discover the enduring history of Maine’s Black community, which, although small, stretches back over four centuries. 

Unearth the stories of national leaders, laborers, skilled workers, activists, and more who tirelessly advocated for freedom and equality, shaping the state’s trajectory. 

From renowned figures like Frederick Douglass to lesser-known Black Yankees, Portland’s history runs deep. Explore the historically Black enclave within Portland’s East End neighborhood under the guidance of a knowledgeable local. Gain insights into notable landmarks such as the Abyssinian Meeting House, Green Memorial Church, Portland Observatory, and more. 

This small-group experience, limited to 15 travelers, ensures an engaging and personalized exploration.

Visiting Portland, Maine: FAQ

We’ve now gone over the perfect day trip to Portland itinerary, discussed the best ways to travel in the city, and sparked a few ideas of where to stay at the end of your adventure. 

Now, let’s make sure you’re completely prepared for your trip by going over a few frequently asked questions.

Best Time To Visit Portland, Maine?

Any time of year can be the best time of year to visit Portland, Maine, depending on the experience that you’re looking for.

Summer offers the warmest weather and extended daylight hours, perfect for extensive outdoor activities. Maine isn’t exactly a beach destination, especially for those of us used to warmer weather. July and August peak at around 79°F, which, to me, is a little too chilly for swimming in the ocean. But if you like cooler water, then it might be the perfect temperature for you. 

Either way, Portland could be a great place to escape the heat of other places (looking at you, Arizona ) during those hot summer months.

The fall is one of the best times to visit Portland, Maine. Maine is one of the most beautiful places to see the colors change, and you’re looking at brisk 59°F temperatures — the perfect degree to wear a sweater and sip a warm pumpkin spice latte.

Winter presents a picturesque scene if you’re fortunate enough to visit during a snowfall, though it’s never guaranteed. Temperatures can plummet below freezing, dipping as low as 14°F, limiting your outdoor adventures. Additionally, be mindful that certain attractions may be closed during the winter months.

Is Portland, Maine, Worth a Day Trip?

As you’ve seen in this itinerary, there are plenty of things to do in Portland, Maine, to fill up a day trip. From some of the best food in the country to fascinating historical monuments to gorgeous lighthouses and seaside views, spending a day in Portland, Maine, is definitely worth the trip.

How Much Time Do You Need in Portland, Maine?

If you want to see everything that Portland, Maine, has to offer, then you’ll want to plan for 3-5 days in town. This will give you ample time to reveal the town’s history, see all the picturesque lighthouses and dramatic views the area has to offer and explore the many, many breweries in town.

However, if you don’t have 3-5 days to spend in town, the above one-day in Portland, Maine itinerary will help you get the most out of Portland with the time you have available.

What To Do in Portland, Maine With 3 Hours?

If you don’t have a full day to spend in Portland and you want to explore this Maine city in just three hours, I’d recommend only doing the following:

• Grab a bite at The Holy Donut.
• Wash it down with a cocktail from Blyth & Burrows.
• Take a look around Exchange Street.
• See the Portland Head Light.

This quick 3-hour itinerary will cover most of Portland’s most iconic sights.

Final Thoughts on a Day Trip to Portland, Maine

This itinerary showcases how much history, diversity, and excitement the little town of Portland really has to offer. Once you’ve explored this charming New England town, you’ll be so glad you took the time to do a day trip to Portland. You’ll probably even want to come back again and dive deeper into this eclectic town!

Dotted with historic lighthouses, filled with a wealth of historic landmarks, and coated with a thick icing of culture, a day trip to Portland, Maine, is one for the bucket list. This carefully crafted day trip itinerary for Portland ensures you make the most of the city’s finest attractions, offering a memorable experience that captures the essence of this splendid little town.

Was this guide useful? Check out our other Portland content here:

• A Walk Through Time Tour in Portland — Genuine Travel Review
• Ultimate Guide to Walking Tours in Portland, Maine in 2024
• The Ultimate Guide to the 59 Best Things to Do in Portland, Maine
• The 5 Most Beautiful Lighthouses in Portland, Maine
• Where to Stay in Portland, Maine: The Ultimate Guide in 2024
• The Complete 2024 Portland, Maine Packing List For Any Time Of Year

Planning another trip? Check out some of our other itineraries here:

• What to do in Phoenix: The Ultimate 5-Day Phoenix Itinerary
• The Perfect Day Trip To Sedona— How To Maximize Your Time
• How to Spend 24-Hours in Phoenix (The Ultimate One-Day Phoenix Itinerary)

Additional Resources:

Ready to book your portland, maine, trip.

Here are a few helpful services:

Booking.com | Find a comfy place to lay your head after a full day of adventuring.

Vrbo | If you’re looking for a more homey vibe, these rental homes might do the trick.

Expedia | Whether you’re looking for some wheels or a flight, you can find a way to get to your destination here.

Get Your Guide | Find local attractions and tours and book tickets to your excursions.

Viator | Another great resource for local attractions and tours.

TSA | If you’re flying, check out the TSA page to make sure that you pack to TSA regulations.

World Nomads Travel Insurance | Feel safe while traveling with simple and flexible travel insurance.

Are you stopping by New York on your East Coast trip? Check out the 72 Best Things To Do In NYC At Night .

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• How to Spend One Day in Portland, Maine

Wondering how to spend one day in Portland Maine? Then you came to exactly the right place to find out. 

Although it’s not a huge city, Portland and the surrounding area are packed with attractions and stunning sights that inform you about the unique history of this old port town. 

This post is here to show you how to see the best of Portland Maine in one day. You’ll finish the guide knowing exactly which museums, lighthouses, and other places of interest to pin to the top of your agenda. 

Read on for the perfect Portland Maine itinerary plus important planning advice to help you arrange how to get there, how to get around, and where to stay in Portland. 

* Disclosure: This post contains a few affiliate links, which means I may receive a small commission, at no cost to you, if you make a purchase through my link. *

Table of Contents

Overview of Your One Day in Portland, Maine

Breakdown of your one day in portland me.

• Morning: Holy Donut, Portland Museum of Art, Wadsworth-Longfellow House & Longfellow Bookstore, Portland City Hall & Merill Auditorium, Portland Peninsula and Island Parishes, Portland Observatory
• Afternoon: Old Port, Fort Williams Park & Portland Head Light, Spring Point Ledge Lighthouse, Bug Light & Bug Light Park
• Evening: Dinner & optional bar hopping

Map for your one day Portland Maine itinerary

Below you can find a customized map that includes all the locations you’re going to visit on this Portland Maine itinerary.

I marked your one day in Portland Maine with different colors – I used blue for the morning, green for the afternoon, and red for the evening, so you can easily see which places you’re going to visit each time of the day.

How to use this map: This map is fully interactive, so you can move around, zoom in/zoom out, and click on the icons. If you want to see a larger map, click on the bracket in the upper right corner. To see more details and the different layers, click on the tab in the upper left corner. If you want to save it for later, click on the star icon next to the name of the map. Then simply open Google Maps either on your desktop or phone, go to ‘Saved’/’Maps’, and open the map whenever you need it.

Morning of Your One Day in Portland Maine

Holy donut .

Start your one day trip to Portland Maine the right way – with a donut! The Holy Donut is located on Commercial Street right in the heart of downtown by the harbor. 

Now, this is not your typical donut place; these donuts are made using a potato base. They come in a variety of innovative flavors including maple bacon, dark chocolate sea salt, honey lavender, and even cannoli. With a starchy base, they’ll fill you up for hours. 

Grab a donut (or three!) and a coffee to enjoy by the harbor before getting started with your sightseeing.

Portland Museum of Art

Once your tummy is content, you can visit the first official attraction of your 24 hours in Portland Maine.

The Portland Museum of Art is an inclusive space that is committed to diversity, accessibility, inclusion, and sustainability. Exhibitions display historical and contemporary paintings and sculptures with works by Picasso, Matisse, Renoir, and Monet.

Note that the museum is closed on Mondays and Tuesdays. Otherwise, it’s open daily 10 am-6 pm and until 8 pm on Fridays. 

Admission is $18 but they offer free entry on Fridays from 4 pm. If that suits you better, you can always jiggle this Portland Maine one day itinerary around. 

The Portland Museum of Art is a 15-minute walk from Holy Donut.

Wadsworth-Longfellow House & Longfellow Bookstore

The Wadsworth-Longfellow House & Longfellow Bookstore is the 19th century home of the poet and thinker, Henry Wadsworth-Longfellow.

You can visit the house on a self-guided or guided tour and peer into Maine history as well as read up on the nation’s beloved poet.

One of the highlights of the museum is the tongue-in-cheek “do not touch” signs that stud each room. Admission is $15 per person. 

Self-guided tours are scheduled by appointment from Tuesday until Saturday between 10 am-3.30 pm and you need to book in advance . You can take a printed pamphlet for details or download a free app before visiting. 

Guided tours only take place on weekdays at 1 pm and 2 pm. 

Remember to have a look around the bookstore too, even if you decide not to visit the museum during your one day in Portland Maine. 

The Wadsworth-Longfellow House & Longfellow Bookstore is a 5-minute walk from the Portland Museum of Art.

Portland City Hall & Merrill Auditorium

Built in 1909, Portland City Hall is the seat of the local government and holds various offices relating to local politics.

It occupies an entire city block and its tower stands at a height of 200 feet (61 meters). Before the construction of this building, an earlier City Hall stood in the same place. 

The Merrill Auditorium, a 1,908-seater concert hall, was added to the eastern section of City Hall. Although it was built in 1912, it underwent a huge renovation in 1997. The star of the Merrill Auditorium is the Hermann Kotzschmar Memorial Organ.

If you are staying for longer than one day in Portland ME then you might want to catch a performance to experience this beautiful venue at its best.

The Portland City Hall and Merrill Auditorium are a 5-minute walk from the Wadsworth-Longfellow House & Longfellow Bookstore.

Portland Peninsula and Island Parishes

The Portland Peninsula and Island Parishes was constructed during the 1860s in the Gothic Revival style. This incredible russet-hued cathedral is the seat of the Diocese of Portland and shouldn’t be skipped from any Portland Maine itinerary.

As a working place of worship, the cathedral hosts daily masses as well as weekend services. Outside of these sessions, you are welcome to go inside and take a closer look at the organ and the stained glass windows. 

The Portland Peninsula and Island Parishes are a 5-minute walk from the Portland City Hall & Merrill Auditorium.

Portland Observatory

The Portland Observatory was constructed in 1807 at the bequest of Captain Lemuel Moody. This octagonal, 86-foot (26 meters) tall tower originally served as a communication station for Portland’s harbor.

Equipped with a powerful telescope at the summit of the tower, Moody could identify incoming maritime vessels as far away as 30 miles (48 km).

Although Portland Observatory fell into disrepair during the 20th century, it underwent renovation and was reopened in 1939. After another round of Restoration in 2000, the Observatory was added to the National Register of Historic Places.

It is the only remaining wooden signal tower and you can visit it from the ground or pay a small fee to explore inside. 

The Portland Observatory is open to the public during the summer season from late May until mid-October.

You can visit it Thursdays, Fridays, Saturdays, Sundays, and Mondays as part of a guided tour. On Tuesdays and Wednesdays, it is only possible to visit as a self-guided tour. 

As the observatory has a limited capacity, it is beneficial to book your tickets online in advance of your 24 hours in Portland Maine. Admission is $10. 

The Portland Observatory is located on Munjoy Hill, a 10-minute walk from the cathedral.

Afternoon of Your One Day in Portland Maine

Old port .

Walk back to the Old Port, close to where you started your one day in Portland Maine. This is the perfect place to have lunch – especially if you like shellfish and seafood with a view.

No surprise what’s on the menu at Luke’s Lobster Portland Pier : you’ll find the likes of iconic Maine lobster rolls as well as lobster bisque, clam chowder, and catch of the day. The atmosphere is laid-back with fantastic ocean vistas.

If you’re not a fan of fish, then check out the upscale Italian eatery, Solo Italiano , which specializes in rustic dishes besides comforting pastas and pizzas. 

Standard Baking Co is perfect if you want a quick sandwich or pastry with a cup of coffee before cracking on with the rest of the day.

Fort Williams Park & Portland Head Light

You will spend the rest of your one day trip to Portland Maine checking out some of the lighthouses. 

There are over 60 lighthouses in Maine and 6 of them are in Portland, owing to the city’s important status as a harbor town during the 18th and 19th centuries.

Sadly, you can’t see that many in one day but you can at least see some of the prettiest lighthouses in Portland .

Portland Head Light is located in Fort Williams Park, Cape Elizabeth. This is 5 miles (8 km) south of Downtown Portland and access is only possible via private vehicle. The drive is 15 minutes from the town center. 

The lighthouse is situated at the entrance of the shipping channel into Casco Bay. It is perhaps the most famous and iconic of the local lighthouses. Constructed in the late 18th century, it was lit for the very first time on 10 January 1791.

You can visit the lighthouse and take photos for free but it costs $2 to enter the museum. Donations are graciously received for the upkeep of the monument. 

Fort Williams Park itself is worthy of a wander if you have time. Make sure to wander along the cliffs for different perspectives on the lighthouse!

Spring Point Ledge Lighthouse

Next up on your Portland Maine itinerary is the Spring Point Ledge Lighthouse.

This one is located back toward downtown Portland. You can drive there in 10 minutes and park near Fort Preble.

Or, if you skip the first lighthouse due to transport issues, you could always take bus number 21 from Portland City Hall, alight at Fort Rd + SMCC, and walk to the Spring Point Ledge Lighthouse.

Spring Point Ledge Lighthouse was built on a rocky promenade in the ocean in 1897. Following several shipwrecks caused by a dangerous ledge, the lighthouse was a welcome addition to Maine’s coastline. 

It’s designed as per a chic monochrome color scheme, making it all the more eye-catching to passing mariners.

There are no costs associated with visiting Spring Point Ledge Lighthouse. But do take care while walking along the boulders to the base of the lighthouse.

Bug Light & Bug Light Park 

The final lighthouse of the day on your day trip to Portland Maine is Bug Light. Officially, Bug Light is called the Portland Breakwater Lighthouse but it usually goes by its nickname due to its tiny size. 

Bug Light is often considered the most beautiful lighthouse in Portland. It looks a little like a classical monument although in its heyday it was just as practical as it was pretty.

The lighthouse was built in 1875 to assist crew navigating their crafts into Portland Harbor. 

Of course, do take some time to explore Bug Light Park which overlooks the Pacific Ocean and has a wonderful vibe during the peak season.

If you don’t have a car, you can book a tour to visit these lighthouses in Portland. There are several options available but for the purpose of this Portland Maine one day itinerary, my personal recommendation is the Portland, Maine Lighthouse Tour – 2 hour Land Tour .

This one is guided by a local lobsterman who also provides professional tours. The meeting place is near the harbor and you will see all three lighthouses described above. 

Note that you will spend longer at Portland Head Light and then make a pitstop at the second two.

The tour price includes round transport and lasts around 2 hours. Subject to availability, you might have to book this tour earlier in the day. In which case you will need to rejig the itinerary.

Evening of Your One Day in Portland Maine

Dinner & optional bar hopping.

That brings your one day in Portland Maine almost to a close. If you are spending the evening in the city then you’ll probably want to enjoy dinner in the heart of town.

You could visit one of the restaurants that I recommended as a lunch spot. Alternatively, here are some additional suggestions.

Taco Escobarr is a colorful tavern with a terrific range of tacos and margaritas. It has a great ambiance and is the perfect place to start an evening out. 

Fore Street Restaurant delivers locally sourced farm-to-table dishes as well as seafood. Upmarket yet with a countryside vibe, this is a great place for a special night. 

If you want to make an evening of it, check out Anoche . This artisanal bar specializes in cider, gin cocktails, and other spirits. Bar snacks including olives, charcuterie, and other small tapas-inspired bites are available.

Maps is another cool place for a drink or two in a close-knit venue brimming with vinyl, books, and vintage maps.

Useful Info for Spending One Day in Portland Maine

Where to stay in portland me.

If you want to see the best of Portland Maine in one day then you’ll likely want to spend at least one night in this charming town. 

Downtown Portland is the most convenient area to stay for a short trip. However, you might want to consider staying in the East End or South Portland if you have access to a car and like the thought of staying away from the hustle and bustle. 

If you’re in a rush, you can take a quick look at my top recommendations below.

LUXURY – Blind Tiger Guest House

Decadent rooms with fireplaces and stylish bathrooms will ensure that your 24 hours in Portland Maine treat you well! Breakfast is included at this central hotel and parking is available at no extra cost. 

MID-RANGE – Aloft Portland Maine

This funky hotel features a bar and a communal games area. Modern rooms are fitted with a private bathroom and a coffee machine. Situated right next to the Old Port, the location couldn’t be better.

BUDGET – Inn at St John Portland In-Town

Breakfast is included in the rate at this pet-friendly hotel in downtown Portland with budget-friendly rates. Rooms are beautifully appointed using a mix of contemporary and old-fashioned decor that feels functional yet homely. 

How to get to Portland Maine

Portland International Jetport (PWM) is the closest airport to Portland. It’s located 2 miles (3 km) west of downtown Portland and only takes 15 minutes to get to a centrally located hotel.

If you are flying in from overseas then you might find better flight availability with Boston Logan International (BOS). It does take 2-2.5 hours to connect to Portland via I-95 N.

However, if your one day in Portland ME falls as part of a wider New England road trip itinerary then this might work better with your schedule anyway. 

You can also connect to Portland from Boston via the Downeaster train. These trains depart frequently from Boston North Station and take 2.5 hours to reach Portland Transportation Center. 

Best time to visit Portland ME

The best time to visit Portland really depends on the type of experience that you are seeking. 

Summer brings the warmest weather and prolonged hours of daylight which is great if you want to spend a lot of time outdoors.

Temperatures peak at 79°F (26°C) in July and August but the city does get extremely busy. Visit in May or June to avoid the worst of the crowds, if possible.

Fall is one of the best times of year to plan your one day trip to Portland Maine. You’ll escape the large summer groups, appreciate comfortable weather conditions, and get to experience the fall colors.

Winter can be pretty if you visit during snowfall but it’s never guaranteed. Temperatures can drop below freezing and get as cold as 14°F (-10°C) which limits how much time you can realistically spend outdoors. Also, bear in mind that some attractions are closed during winter. 

How to get around Portland Maine

Once you’re in Portland, you can explore the main downtown area on foot or by hiring a bicycle.

There is a bus system called the Greater Portland Metro that connects you with local destinations as well as the Amtrak Downeaster, Casco Bay Ferry, and Portland Jetport.

A ferry service connects Portland Harbor with the outlying islands in case you end up spending longer than one day in Portland Maine.

There are a few places on this itinerary that it is trickier to reach without hiring your own vehicle. So, if you do rent a car that will be a huge bonus.

Planning a trip to New England?

Then you might want to take a look at all our other travel guides about New England. I promise, they are just as awesome as this article was!

• The Perfect New England Fall Road Trip for 2 Weeks
• Vermont in the Fall: Travel Tips & Best Places to Visit
• 16 Incredible Things to Do in Woodstock VT
• 17 Amazing Things to Do in Stowe, Vermont
• 17 Incredible Covered Bridges in Vermont You Need to Visit
• 81 Amazing Vermont Quotes & Captions for Instagram

New Hampshire:

• Kancamagus Highway Fall Foliage Drive: 9 Best Attractions & Tips for Visiting

Massachusetts:

• How to Spend One Day in Boston: Itinerary & Best Things to Do
• 13 Best Day Trips from Boston You Can’t Miss
• Where to Stay in Boston: 8 Best Areas & Hotels
• 133 Best Boston Captions for Instagram (Quotes, Puns & More)
• 19 Spooky Things to Do in Salem MA in October
• How to Spend One Day in Acadia National Park
• The Perfect 2 Days in Acadia National Park Itinerary
• Acadia National Park in the Fall: Practical Info & Tips for Visiting
• 5 Prettiest Lighthouses in Portland Maine You Can’t Miss

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3-Day Portland, Maine Itinerary

By Author Daina Grazulis

Posted on Last updated: June 22, 2022

Categories MAINE

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Portland, Maine – The Small “Big” City

This 3-Day Portland, Maine Itinerary has everything you need to know about exploring the most populous city in the state!

Welcome to Portland, Maine! This is an incredible city full of rich history, amazing restaurants, fun bars, and beautiful ocean views.

I like to call Portland a small “big city.” It has that distinctly urban downtown vibe, but a relatively small population to be considered “big.” At roughly 67,000, Portland is the most populated city in the entire state of Maine.

Portland has an unmistakable charm that shines through in its narrow cobblestone streets, historic brick buildings, and traditional colonial townhouses. These elements mix wonderfully with the modern storefronts and art galleries that line the main streets of the city.

In recent decades, Portland has morphed from simply a town necessary to pass through for tourists to get to other parts of Maine to a destination city in itself.

It’s a fun and exciting place to explore – perfect for a romantic getaway or a weekend out with friends. This 3-Day Portland, Maine Itinerary has everything you need to know for your stay.

For more suggestions on what to do in the area, check out these 46 Fun Things To Do In Portland, Maine.

Don’t forget to check out our most recent Maine travel blog posts: – 10 Sandy Beaches Near Portland, Maine – The Best Pick Your Own Apple Orchards in Maine – 7 Best Coffee Shops in Portland, Maine

Fun Facts About Portland, Maine

• Did you know Portland, Oregon was named after Portland, Maine? The most populated city in Oregon was founded by a pair of New Englanders—Boston’s Asa Lovejoy and Francis Pettygrove from Portland, Maine. Each man wanted to name the spot after his hometown. So, they settled this matter the right way—via  coin toss.  Pettygrove won two out of three flips and that was that.
• Roughly 40 percent of all Maine residents live in the greater Portland metropolitan area.
• No transatlantic port in the U.S. is closer to Europe than Portland. According to the city’s official website, it’s also America’s 20th-largest fishing port.
• Acclaimed poet Henry Wadsworth Longfellow and author Stephen King were both born in Portland. King still maintains a residence in his native state; he and his wife Tabitha divide their time between Florida and the city of Bangor.

Day 1 in Portland, Maine

Time to explore and get acquainted with this historic seaside city! This includes shops, museums, lookouts, and bars.

Old Port/Congress Street

Portland’s historic Old Port cobblestone streets are lined with cute boutiques, touristy shops, art galleries, restaurants, and bars.

Start down on Commercial Street by the water, and work your way up the bustling Exchange Street. I’m personally a huge lover of bookstores, so that’s typically where I spend most of my shopping time downtown.

My favorites are Longfellow Books and The Green Hand – check out this complete list of bookstores in and near Portland! Another must-see shop is Flea For All .

Portland Observatory

The  Portland Observatory  is a historic maritime signal tower at 138 Congress Street in the Munjoy Hill section of Portland.

Built in 1807, it is the only known surviving tower of its type in the United States. Using both a telescope and signal flags, two-way communication between ship and shore was possible several hours before an incoming vessel reached the docks.

It’s now a tourist attraction that provides historical context and amazing views of Portland and the ocean.

The  Portland Museum of Art , is the largest and oldest public art institution in Maine. It was founded in 1882. It is located in the downtown area known area The Arts District in Portland, Maine.

The Museum’s collection includes more than 22,000 artworks, dating from the 18th century to the present. Visitors under 21 years old always get free admission, and entrance is free to all every Friday from 10am to 8pm.

The Maine Historical Society Museum features changing exhibitions and programs spanning more than 12 centuries of Maine life. Drawing from the extensive collections of the Maine Historical Society, original exhibits feature art, artifacts, stories, and documents that vividly bring Maine history to life.

These museums are both located down Congress Street from each other. These are perfect activities for a rainy or hot day when you just don’t want to be outside.

Portland has a flourishing bar scene that comes alive in the evenings and on weekends. There is truly something for everyone from dancing club bars to live music venues to intimate cocktail lounges.

My favorites include the hidden speakeasy Lincoln’s , a basement bar decorated in vintage maps and records called Maps , and the live music bar Blue . Check out my Portland, Maine Bar Guide for more information on enjoyable bars in town.

If you don’t drink alcohol, you can still participate in the festivities!

Vena’s Fizz House specializes in expertly crafted mocktails. Other bars with non-alcoholic cocktails on the menu include Central Provisions , Sagamore Hill Lounge , and the Portland Hunt & Alpine Club .

Where To Eat Day 1:

For lunch, check out Pai Men Miyake for amazing sushi and ramen bowls, or The Thirsty Pig for delicious house-made sausages and an extensive craft beer tap list.

Stop by David’s for an affordable high-end happy hour. Thai food at Boda or seasonally inspired farm-to-table American food at The Little Tap House are great options for dinner in the area.

Day 2 in Portland, Maine

Today is all about enjoying the two best things Portland has to offer – ocean views and beer. Don’t forget to bring a sweatshirt and have safe and sober rides around town!

Farmer’s Market

The Portland Farmers’ Market has been in operation since 1768! Whether it’s early spring, the heat of summer, a crisp fall morning, or a snowy winter day, the Farmer’s Market has something fresh and healthy for everyone.

If it can be grown or produced in Maine, you’ll find it at the Portland Farmers’ Market. The few times I’ve walked through the market, I was amazed at the overall variety of products being sold.

The best part is that they’re all local, mostly organic, and fresh! You’ll find every kind of seasonal vegetable, a huge variety of animal meats and cheese, fermented goodies, fresh baked goods, art, and homemade jewelry.

Casco Bay Lines Mail Boat

The Mailboat is an incredible way to experience Casco Bay from the sea. This true working boat carries passengers, mail, and freight to several islands off the coast of Portland.

A ticket gets you a 2-3 hour boat ride, and the option to hop off at any of the islands including Little Diamond, Great Diamond, Long, Cliff, and Chebeague. Just be sure to have a copy of the mail boat schedule so you know when you can hop back on to make it back to Portland.

Don’t forget to bring a sweatshirt or light jacket, even in the summer. Temperature and winds out on the water can be very different from the coast. For more information about the different islands and Casco Bay Lines Ferries, click here.

If you have time, this is one of my absolute must-dos in this 3-day Portland, Maine itinerary! There is simply nothing like the fresh ocean air to go with some of the best views you’ll find in all of Maine.

There are a lot of craft breweries in Portland (dare I say too many?). It’s a great city for beer lovers who want to enjoy some cold Maine brews on a Saturday afternoon.

Even if you don’t drink beer, many breweries do serve cider, wine, cocktails, or craft soda. There are breweries all over Portland and the surrounding areas, so you have several options for how to tour them.

You can hitch a ride by booking a Maine Brew Bus craft brewery tour. The all-inclusive tours provide a behind-the-scenes look at Maine’s craft breweries, distilleries, wineries, and more. Tours are led by expert guides in addition to a knowledgeable non-drinking driver to ensure the best possible experience.

You could take a walking tour of several breweries in the same area within walking distance from downtown Portland. Or, if you do decide to have someone in your party drive you around, make sure to be safe!

Here’s a full guide to the best breweries in Portland, Maine.

Even if you decide not to do an entire tour of the breweries, at least visit one as part of your Portland, Maine itinerary. It’s said that Portland has the most breweries per capita in the entire US! My absolute favorites are Foundation Brewing , Lone Pine , and Allagash .

Where To Eat Day 2:

Portland has some AMAZING breakfast restaurants , so you really can’t go wrong in that department. Try out Miss Portland’s Diner near Deering Oaks Park before hitting up the farmer’s market.

Pack a picnic of artisan charcuterie to enjoy on the mail boat with items from Rosemont’s Market . If you’re hungry on the brewery tour, both Sebago Brewing (get the waffle fry potato nachos, just trust me) and Foulmouthed Brewing have excellent food.

For a romantic dinner out, try Ribollita for some mouth-watering house-made Italian food.

Explore the abundant nature that Portland and its surrounding areas have to offer. Wear some comfy walking shoes and expect to be dazzled by all the natural beauty you’re about to experience!

Eastern Promenade

The Eastern Promenade was designed in 1905 by the Olmsted Brothers landscape firm, renowned for creating New York’s Central Park and the Boston Commons.

Today, the 68-acre historic landscape on the northeastern slope of Munjoy Hill (east end of Portland peninsula) offers unparalleled views of Casco Bay and Portland Harbor.

This is one of the best spots for a picnic in Portland (although there are many awesome contenders!), and is a beautiful place to watch the sunrise.

There is a 2-mile trail that runs along the coastline in addition to basketball and tennis courts, a baseball field, and a playground. Even if you decide not to spend any time hanging out on the Eastern Promenade, it’s worth a drive-by to get the most expansive view of the Casco Bay in the city!

Gilsland Farm

Gilsland Farm is located about a 15-minute drive away from downtown in Falmouth. It’s home to the Maine Audubon Society headquarters and is my favorite paradise away from the noise and activity of the city.

I’m always amazed at how much wildlife I see every time I visit, even if it’s just for a short walk. There are 3.5 miles of networked trails that lead through expansive wildflower meadows and forests.

The property runs along the Presumpscot River Estuary, providing some lovely and peaceful scenery just outside of Portland.

If you’re interested in exploring more trails around the area, check out these 8 easy hiking trails near Portland, Maine.

Bug Light Park

This is my favorite spot to catch a view of the Portland skyline. Pack a picnic, grab a book, and go relax on the expansive grassy lawn facing the big city at this cute park in South Portland.

This is a lovely place to kill a couple of hours on a nice day. There is also a small, cute lighthouse that juts out into the bay.

Portland Head Light

Okay, I couldn’t make a Portland, Maine itinerary without including the famous Portland Head Light.

It’s situated along the spectacular shores of Fort Williams Park in Cape Elizabeth about 5 miles outside of Portland. The park has absolutely amazing views of the ocean and rocky Maine coastline.

There is a half-mile-long beautifully landscaped Cliff Walk that leads up to the lighthouse – it’s my favorite part of the entire park!

I write more about it in another post – 11 Public Gardens In Maine. Join in the fun and take a picture of Portland Headlight – it’s reportedly one of the most photographed lighthouses in the country.

Lobster Roll

There is a lot of debate about where you can get the best lobster roll in Portland.

Personally, I aim to get the best bang for my lobster roll buck instead of frequenting the trendy and “boutique” lobster joints. I’m sure those places make for great Instagram photos, but that’s not what I’m after in a lobster roll!

With that being said, the absolute best place to grab a lobster roll or dinner in the greater Portland metro area is The Bait Shed in Pine Point.

It is about a 20-minute drive from downtown Portland, but it’s totally worth it. Patrons are seated on a deck that juts out into the Scarborough River.

Where To Eat Day 3:

I hope you have a big sweet tooth! For breakfast, head over to Artemisia Cafe for a wholesome and fresh artisan breakfast.

While you’re in South Portland, grab a crafted latte at Omi’s Coffee Shop . Pick up a baked treat at Omi’s, Scratch Baking Co , or The Cookie Jar (or get something from all 3! No judgment here!).

The Cookie Jar has the absolute BEST donut holes and donuts in the Portland area. Have a humongous lobster roll or another seafood dish at The Bait Shed for lunch (see above).

Head back on down to South Portland for the best dinner you’ve ever had at David’s 388 (I’m not kidding, it’s AMAZING!).

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Saturday 10th of December 2022

Fantastic Info....planning a trip for June...Can you suggest places to stay? Or best neighborhoods?

Caroline Savage

Thursday 30th of September 2021

I would update your suggestions with mask information or least the Maine CDC website. And maybe the date you updated.

Monday 6th of September 2021

Peaks Island is also a great place to visit, but I am a little biased cause my cousin lives there and owns the greenhouse just up the hill from the ferry dock. There's a spot known as whaleback that is my serenity place. I could sit there all day with a good book and bottle of wine. And Battery Steele is quite interesting.

Daina Grazulis

Tuesday 7th of September 2021

I agree! After publishing this blog post, I realized I left out a few things that should be on this list - I will be updating it soon, and Peaks Island will definitely be added!

Saturday 26th of June 2021

We are flying into Boston and driving to Maine early October (Thursday-Tuesday)- our first trip! Recommendations on places to stay? I was thinking we should take a tour to see the fall leaves after we arrive in Boston then stay in Maine after. Your information has helped greatly but I am having issues coming up with an itinerary.

Sunday 4th of July 2021

Hi Danielle! Sounds like a nice trip - depending on your timeline, I would suggest staying in Portland, Bar Harbor, or Camden. I plan on posting some more articles this summer about fall activities/itineraries, so I'll let you know when those are up!

Marie Moreland

Wednesday 9th of June 2021

Thank you for this information! I will be in Maine next month and have not been able to find a travel book for it. This info is great and I will print it off to take with me! I have copied 3 days in Portland and 9 hikes in/near Bangor. Other recommendations??? Thanks again!

Friday 11th of June 2021

Hi Marie! I hope you enjoy your trip to Maine! I just posted another article with 14 fun things to do in Belfast, Maine (one of my favorite cities in the state). DEFINITELY stop by the Coastal Maine Botanical Garden in Boothbay Harbor - it's amazing (I also have an article with 11 beautiful public gardens in Maine). Honestly, if you're just visiting, I would not stop in Bangor, it's not really an exciting place for tourists. The Belfast/Camden area is a much better place to hangout.

The Perfect 3 Day Portland, Maine Itinerary

Looking for your next trip to the east coast this 3 day portland, maine itinerary has everything you need to start planning.

Portland is a fascinating city along the southern coast of Maine and is absolutely worth seeing. Its quaint, everlasting essence is what charms travelers and makes it one of the most cherished places to visit for those in the state.

The moment you step into this inspiring city, you will be immersed in its glorious history rich in fishing, agriculture, and of course industrial growth.

The perfect amount of time to spend in Portland, Maine is 3 days.

You’ll be able to see beautiful coastal lighthouses, enjoy the delicious food scenes, and walk along the charming cobblestone streets!

3 Day Portland Maine Itinerary

How can i spend 3 days in portland, maine.

For those thinking about spending time in the fun city of Portland, it’s time to break down what a 3 day Portland, Maine itinerary should encompass!

🚗 The best place to rent a car online is through Discover Cars for Portland, Maine. They provide the best deals for car rentals in Maine!

If you’d like to experience more of New England, check out this 10-day road trip itinerary !

Without further ado, read on for all the deets of making the best of your 3 day Portland, Maine itinerary!

Day 1: Old Port, Food Tour, Portland Head Light

1. Visit The Old Port & Downtown Area

There is nothing more “Portland-Esque” than visiting the Old Port . This is one of the more historic and traditional attractions in this coastal city and it is going to be a place you will remember.

The brown-colored buildings with welcoming locals everywhere can be heartwarming. Old Port also is lined with cobblestone paths, which just adds another layer of charm.

A few of my favorite stores to browse through were Pinecone + Chickadee , Life is Good , and Maxwell’s Pottery .

This is also a food hub for those who want to take in the sights while enjoying what local eateries are all about. Just stop by, order a meal, and get some of the best food you are ever going to find.

A couple of notable restaurants are Duckfat for some Belgian fries and The Honey Paw for Asian fusion.

This is a delicious part of Portland and a great introduction to what the city has to offer. You will love it as a starting point.

2. Take A Culinary Tour Near Old Port for Lunch

Since you are going to be around Old Port, it’s time to dig deeper into what the region has to offer. This is a complete walking food tour that is going to show the ins and outs of the culinary delights associated with this part of Portland, Maine.

You will learn more about the history of seafood, how it is made, and which meals are must-eat in this beautiful city. There is enough food that you will be filled up for lunch!

The tours are kept smaller for a personalized experience, just make sure you’re wearing great walking shoes like my favorite Bob’s shoe or these Skechers !

>> Book your Culinary Tour Near Old Port ! <<

3. Visit the Holy Donut for Dessert

After your culinary food tour, head on over to the Holy Donut for a sweet treat. These riced potato donuts are delicious and a must-try when in Old Port. Some of the best flavors are the Triple Berry, Honey Lavender, and Dark Chocolate Sea Salt.

You can continue browsing in Old Port as you snack, or save your donut and drive to the Portland Headlight for a view!

• Holy Donut | Address: 177 Commercial St, Portland, ME 04101

4. See Gorgeous Views at Portland Headlight

The Portland Headlight is located in Cape Elizabeth, Maine, and is a beautiful spot to take in the views of the Atlantic Ocean and Casco Bay. The lighthouse was constructed in 1791 and is still operational today. It’s definitely worth a visit if you’re in the area!

Take your Holy Donuts and grab a spot at one of the picnic tables to enjoy the sea breeze. If you’re feeling active, there’s a trail that takes you over some rocks to see the headlight from the cliffs. The views are simply breathtaking!

For a more relaxing activity, take a walk on the beach and get some amazing pictures of the lighthouse. You’ll definitely want to remember your trip to the Portland Headlight!

• Portland Head Light | Address: 12 Captain Strout Cir, Cape Elizabeth, ME 04107
• Free parking in Fort Williams Park
• Entrance fee into the lighthouse | Adults: $2 | Children 6-18: $1 | Under 6: Free

5. Eat at J’s Oyster

Now it is time to wrap up the day with a good meal. J’s Oyster does it all with its welcoming ambiance, spacious seating, and overall high-quality seafood.

Whatever you order here is going to impress. Whether it is the lobster roll or stew, you will want to fill yourself up with some of the finest seafood in the area.

Nestled right along the water, this is a fun-filled experience for those who want to enjoy good customer service, fun people, and great food. It is the perfect trifecta in that sense and a good way to wrap up day one.

• J’s Oyster | Address: 5 Portland Pier, Portland, ME 04101

Day 2: Museums, Sight Seeing, Lobster Rolls

1. Check Out Some Local History at the Portland Museum of Art

The Portland Museum of Art is about a 4-minute drive or a 13-minute walk from Old Port. The museum is passionate about providing art for all by including people of all backgrounds to experience its art. There are rotating exhibits, so there’s always something new to see.

One of my favorite things about this museum is that there is a sculpture park that takes you outside. It’s quite an incredible view!

If you’re looking for a dose of culture, the Portland Museum of Art is definitely worth a visit!

• Portland Museum of Art | Address: 7 Congress Sq., Portland, ME 04101
• Open Hours | Wednesday – Sunday, 10 am – 6 pm
• Entrance Fees | Adults: $18 | Seniors + Students: $15 | 21 years and under: Free

2. Go For Burrito at Crunchy Poke

When it is time to eat, you will want to step away from the seafood and try out something new in the form of a Portland burrito. Crunchy Poke is a fun, easy-going restaurant that offers some of the best seafood burritos you are ever going to taste!

If you’re not into seafood burritos, you can also grab a poke bowl to enjoy all the flavors of seafood. Whatever you choose to order, you can’t go wrong!

The place is always welcoming and offers a more authentic seating experience in this small city. You will experience Portland in a way that is unique, memorable, and perfect.

• Crunchy Poke | Address: 426 Fore St, Portland, ME 04101

3. Get Some Views From the Top at the Portland Observatory

The Portland Observatory is about a 4-minute drive or an 18-minute walk from Old Port and it offers some of the best views of the city. The observatory was built in 1807 and is the oldest standing structure in Portland.

The observatory is open for tours from May through October, and it’s definitely worth a visit. You’ll be able to see the harbor, Old Port, and the Portland skyline from the top.

If you’re visiting Portland, make sure to add the Portland Observatory to your list of places to see!

• Portland Observatory | Address: 138 Congress St, Portland, ME 04101

4. Grab a traditional Maine Lobster Roll for Dinner

When you think of Maine, one of the first things that come to mind is lobster. And what’s a better way to enjoy lobster than in a traditional lobster roll ?

A lobster roll is simply a roll of lobster meat, mayo, and celery that’s been chilled. It’s usually served with a side of fries or onion rings.

If you’re in Portland, there are a few places where you can get your hands on a lobster roll. One of my favorites is the Portland Lobster Company . They have a great outdoor seating area where you can enjoy your meal with a view of the harbor.

Another great option is DeMillo’s on the Water . They have an extensive menu with a lot of great seafood options. The lobster roll is definitely worth a try!

A third option to get a lobster roll is at Eventide Oyster Co . They serve up some of the best seafood in the city, and the lobster roll is no exception. It’s definitely a must-try if you’re in Portland!

• Portland Lobster Company | Address : 180 Commercial St, Portland, ME 04101
• DeMillo’s on the Water | Address: 25 Long Wharf, Portland, ME 04101
• Eventide Oyster Co. | Address: 86 Middle St, Portland, ME 04101

5. Visit Bubba’s Sulky Lounge For Dancing Fun

When you are on a trip, you will want to have a bit of relaxed fun. This is where Bubba’s Sulky Lounge comes into the equation with its welcoming patrons, fun-filled tunes, and inviting ambiance.

Whether you are thinking about grabbing a drink after dinner or having a bit of fun dancing, there is something for everyone here and that is what makes it appealing. You’ll also find a plethora of antiques as that’s one of Bubba’s favorite hobbies!

Portland is home to several of these places but there is nothing better than spending time at Bubba’s.

• Bubba’s Sulky Lounge | Address: 92 Portland St, Portland, ME 04101

Day 3: Peaks Island, Bug Light Park, Cocktails

1. grab breakfast at hot suppa.

Hot Suppa is a southern breakfast restaurant about a 5-minute drive or a 20-minute walk from Old Port. The restaurant is known for its creative breakfast dishes, and it’s definitely a must-try if you’re in the area.

The atmosphere of the restaurant is cozy and comforting. It’s the perfect place to start your day.

My personal favorites are the chicken and waffles and the mother clucker, which is boneless fried chicken served with cheddar curds and biscuits. If you’re looking for something sweet, try french toast. It comes spiced with vanilla, cinnamon, and nutmeg, yum!

No matter what you order, you’re sure to enjoy your breakfast at Hot Suppa. It’s definitely one of my favorite breakfast spots in Portland!

• Hot Suppa | Address: 703 Congress St, Portland, ME 04102

2. Head To Peak’s Island For Exploration

It’s the last day of your 3 day Portland, Maine itinerary! One of the coolest places to visit is Peak’s Island . This is one of the most breathtaking parts of the coastal city and an experience you are going to thoroughly enjoy.

Peak’s Island is accessible by ferry and is quite the sight during the warmer months. It is rich in greenery, has open spaces, and offers a look at a historic part of the region in the form of a WW II outpost. The area is dripping in history due to this reason.

Even if you are not a history buff, the visual appeal of Peak’s Island is reason enough to want to visit it.

You can rent a little golf cart and drive around the whole island or hang out on the beach. One of my favorite activities was driving around the neighborhoods to peep the adorable coastal homes – they also have names!

Make sure to check the Peak’s Island ferry boat schedule so you can plan accordingly!

• Peak’s Island | Address: 20 Island Ave, Portland, ME, United States

3. Eat Lunch At Bao Bao

You can grab lunch at Peak’s Island, but if you are returning to the main part of Portland for lunch, check out Bao Bao, another well-established restaurant that offers quality food using the best recipes.

Bao Bao is a dumpling house where you can order dim sum or dumplings. This starts with wonton soup, pork and scallion dumplings, or beef bulgogi dumplings.

The crisp, mouthwatering taste of their menu items will make you want to stay there and keep eating. It is one of the biggest allures of Bao Bao because the food is fantastic and the atmosphere is welcoming.

• Bao Bao | Address: 133 Spring St, Portland, ME 04101

4. See the Sunset at Bug Light Park

If you’re looking for a beautiful spot to watch the sunset, look no further than Bug Light Park . The park is located in South Portland, Maine, and offers stunning views of the harbor.

Even more than the views it offers, Bug Light Park also has a great history of being the site of shipbuilding activity during WWII. The lighthouse was built in the late 1800s in Grecian style and was dubbed “Bug Light” due to its small size.

You can participate in some activities like picnicking, kite flying, and boating at Bug Light Park, but one of the best times to visit is in the evening when the sun is setting.

The park is a great place to relax and take in the beauty of nature. It’s definitely a favorite spot in Portland!

• Bug Light Park | Address: South Portland, ME 04106
• Open Hours | Every day,  6:00 AM – 9:00 PM

5. Grab A Drink At Liquid Riot

When it comes to ending your day, you will want to grab a drink at Liquid Riot . This is one of the best gourmet bars in the region and an experience that is an attraction all by itself.

It all starts with the housemade beers and spirits. It is a setting that is a different take from other establishments in the city making it one-of-a-kind in that regard. Some of the beers include Spaceman Spiff, Stereotropic DIPA, and Special Ale.

The long rows of seating, elegant lighting, and charming staff will ensure you have a good time. This is a wonderful place to drink with family and friends while traveling.

• Liquid Riot | Address: 250 Commercial St., Portland ME  04101

Map of Things to do in Portland, Maine

Key: Yellow – Day 1 | Blue – Day 2 | Green – Day 3 | Pink – Accommodations

Extending Your 3 Day Portland, Maine Itinerary

Head to bar harbor + hike in acadia national park.

If you would rather take your time exploring northern Maine , take a 1-hour drive up from Portland, Maine to spend some time in Bar Harbor. There is plenty to do in the small town, from hiking and biking trails to visiting the local shops.

Don’t forget to drive through Acadia National Park ! The park has some of the most beautiful scenery on the east coast. Make sure to stop at Jordan Pond House and try a popover with jam.

There are plenty of hiking trails to choose from in Acadia National Park, but make sure to head out earlier so you can see the views! A couple of my favorite hikes are the Bubble Trail , an easy-to-moderate trail, and the Beehive Trail , a moderate to difficult trail.

Overall, Bar Harbor is a laid-back small town to spend a few days in and is the perfect home base for exploring Acadia National Park.

• Portland to Bar Harbor Drive Time: 1 Hour
• Jordan Pond House | Address: 2928 Park Loop Rd, Seal Harbor, ME 04675

Read Next: The Ultimate 10 day New England Road Trip Itinerary [Portland to Boston Drive]

Take a Road Trip Down to Boston

If you have a few more days to spare, take a road trip down to Boston and check out this amazing, historical city! There is so much to do and see in Boston–you won’t regret stopping by.

One of the coolest things to do in Boston is to walk the Freedom Trail where you take a self-guided walk through some of the most historical sights in American history: Park Street Church, Granary Burying Grounds, Old South Meeting Hall, Faneuil Hall, and so much more!

If you’re into whale watching , you can also take a boat tour to the Stellwagen Bank National Marine Sanctuary . You can also take a short trip to tour Harvard University (and claim that you went there).

The drive from Portland down to Boston is about 2 hours long.

Where to Stay for a 3 Day Portland, Maine Itinerary

Luxury option: canopy by hilton portland waterfront.

When it is time to find a place to stay in Portland Maine, staying near Old Port is ideal, making it easier for you to tour the area, take in the great seafood options, and make the most of your trip.

Since you will want to spend time in the downtown area and around Old Port, Canopy by Hilton Portland Waterfront is a good place to stay. It will keep you close to the key areas while also ensuring you can branch off later too.

The hotel itself has a long list of amenities, is well-known, and remains clean year-round.

>> Check availability for the Canopy by Hilton Portland Waterfront! <<

Mid-Range Option: The Press Hotel

This is a recommended place to stay for those who want to stay central in the city but also have a bit of money to spend. The luxuries associated with The Press Hotel are different from the other options and that makes it far more enticing to some people.

The gorgeous rooms, long list of facilities, and overall ambiance is nothing to scoff at. You will appreciate it as soon as you walk through the front door.

This is a hotel with a purpose and a beautiful place to spend 3 days in Portland, Maine.

>> Check availability for The Press Hotel! <<

Budget Option: Portland Regency Hotel

The Portland Regency hotel is in an ideal spot as it is central to everything. This makes it ideal for those wanting to visit different areas of Portland without having to steer too far away from where they are staying at night.

The hotel is well-located, offers exceptional service, and makes it easy to enjoy your stay in a spacious room. The brand is appreciated locally for its luxury and you are going to get to make the most of it by staying here.

If you want a central location, this is a hotel to have on your list.

>> Check availability for the Portland Regency Hotel! <<

When is The Best Time to Visit Portland, Maine?

When visiting Portland, it’s never a bad idea to time your trip to perfection. The summer months are perfect in Portland making every day a breathtaking one.

However, summer is the high season for Portland between June and August, so you might find more crowds during the warmer months.

The temperature tends to hover between 65°F-73°F. This is comfortable, breezy, and works well at all times of the day. You also have less rain to deal with and that makes Portland, Maine quite appealing to those visiting and heading outdoors to places such as the beach.

September and October are also good months to visit as the temperatures are still in the 70s, there are fewer crowds, and you get the beautiful fall foliage and bright colors!

Getting Around Portland, Maine

When it is time to plan your 3 day Portland, Maine itinerary, it’s important to pinpoint how you are going to handle transportation.

If the transportation is not planned, you will have a stressful time getting from one part of Portland to the next. While it is a small city, you do need transportation to get the most out of it.

Consider all these options based on what your budget is so you can fully enjoy your 3 days in Portland, Maine.

• While in and around Old Port, you could walk to most of the sites. To get from the airport to your accommodation, you can take a Lyft or Uber.
• You could also take the Portland METRO Bus to get around the city as well. This works well when you are in the downtown area and/or looking to get to places that are a few minutes away.
• We personally rented a car when we visited because we were planning on visiting other cities as well. This may be the most efficient option for you, too, if you would rather not worry about figuring out the METRO stops or ordering Lyfts/Ubers.

🚗 When booking your Portland, Maine car rental online, I recommend using Discover Cars . They provide the best deals for car rentals in Maine!

How to Pack for a 3 Day Portland, Maine Itinerary

With temperatures in the 70s, you can get away with shorts in Portland. You’ll definitely want a jacket for when you visit the coast or see the gorgeous lighthouses!

👟 Shoes: Pack comfortable walking shoes so your feet can fully enjoy all the walking you might choose to do. Also, pack a pair of sandals for easy change.

🧥 Jacket: Bring a light jacket for those chillier evenings.

👚 Clothing: For 3 days in Portland, pack 3-4 shirts and 1-2 bottoms which can be shorts or pants. This way you can mix and match your outfits.

👗 Dress: It’s always nice to have a dress around just in case you want to dress up a little bit for the night out or that Instagram shot.

☀️ Protection: While you’re out and about, protect your skin with sunscreen and a hat .

FAQs: 3 Day Portland, Maine Itinerary

Can you do a day trip to acadia national park from portland.

The short answer is yes, you can do a day trip to Acadia National Park from Portland, Maine, but I would not recommend it.

It is about a 3-hour drive from Portland so you would have to start your day very early and start your drive back to Portland earlier in the evening.

Instead, I would recommend making an overnight stay in Bar Harbor, a small coastal town right outside of Acadia National Park. Then you can have all the time in the world to explore Acadia and get a couple of meals in Bar Harbor.

Is Portland, Maine a walkable city?

Yes, Portland, Maine is a walkable city. Plan to stay in Old Port so that you can have walking access to all the good stuff–food, shopping, and sights.

One of the most popular places to visit is the Portland Head Light. If this is on your bucket list, then I would recommend renting a car or calling an Uber because it would be hard to walk that distance.

Is downtown Portland worth visiting?

Absolutely. As mentioned above, Old Port is part of the whole of downtown Portland. You can walk from West End to East End and find gems of all kinds in Portland. Put on your walking shoes and start exploring!

Final Thoughts: 3 Day Portland, Maine Itinerary

This is a city with an unrelenting elegance that is impossible to ignore. You will enjoy your time along the coast with its scenic views, tourist-friendly eateries, and gorgeous weather.

As you begin to plan things out, you will want to have this all-encompassing 3 day Portland, Maine itinerary on hand at all times.

Are you ready to head to the east coast? Check out more resources!

• 10 Day New England Road Trip (Portland to Boston)
• 3 Day Portland Itinerary
• Best Walking Tours in Portland
• One Day in Camden, Maine
• Boston to Wells Road Trip
• Day Trips from Boston by Train (MBTA Weekend Pass)

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My favorite travel tips + resources.

Here is a quick glance at all my go-to travel tips and resources that I use to plan every trip! For more information, check out my travel resources page .

• Booking flights: I use Google Flights to check all routes and find the best flights. Then I compare Skyscanner (for the lowest prices) before I book.
• For hotels, I go through Booking.com or book directly with Marriott (for points + rewards).
• When I travel internationally, I’ll book through Hostelworld for very budget-friendly stays.
• For vacation rentals, use Vrbo or Marriott Homes & Villas .
• Expedia also has some great bundles for hotels, flights, and car rentals altogether.
• Car Rentals: I love renting cars through Discover Cars . They have been consistent and provide the best customer service.
• Trains in Asia: Trip.com has the best options!
• Trains in Europe: Trainline or Omio .
• Visa Application: For a hassle-free process, apply for your visa from iVisa .
• Travel Credit Card: I book all my travel (flights, hotels, car rentals) through Chase Sapphire .
• Vaccines and Medications: Check the CDC website for updates on necessary vaccines to enter a country, including updates on Covid-19 and recommended places to visit. I recommend getting all the vaccines you need before you go!
• Tours + Experiences: I absolutely love my tours! Everything from eerie walking ghost tours to food tours, I’ll usually book something every trip either through Viator or GetYourGuide .
• Entertainment: Looking for entertainment like sporting events, theater shows, or concerts? Book with Ticket Squeeze !
• Tech : Keep your internet browsing safe, secure, and fast with ExpressVPN
• Language Learning: The best place to learn a new language is through Babbel as you travel to countries you don’t know the language.
• What to Pack: I almost always travel by backpack . For products I like, check out my packing guide page for all the things I take with me on different trips.

Pafoua is the author and creator of Her Wanderful World. Pafoua writes from her numerous excursions about all things travel, from fun itineraries to creating memorable experiences on the road. When she’s not traveling, Pafoua loves a fun board game night with her friends or is snuggled up reading a good book. You can find her on Instagram @herwanderfulworld.

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The BEST things to do in Portland, Maine (+ a two day itinerary option!)

Last updated on March 11th, 2024

Portland, Maine is one of our favorite cities in the United States and in this guide we’re sharing the best things to do in Portland, Maine, plus a two day itinerary! For our final stop on our big month long New England road trip we headed to Portland, Maine, which is a city we had been looking forward to visiting for so long. And it was basically love at first sight! With a historic downtown area, gorgeous waterfront views, an amazing restaurant scene, and unique activities, Portland had a vibe that we meshed with so perfectly and during our few days in the city, we had the best time trying delicious local foods, wandering around town, and even catching lobster. It quickly became one of our favorite cities we have been to!

Check out our time in Portland, Maine, including exploring the city and going lobstering !

Ready to experience this beautiful city for yourself? In this guide we’re sharing the best things to do in Portland, Maine, as well as all of our insight from our visit to this city, including where to stay, when to visit, how to get around, and a two day Portland, Maine itinerary to help you prioritize your time. We hope you fall in love with Portland like we did!

Looking for more things to do in Maine and New England? 

• New England Fall Road Trip Itinerary
• Our Favorite Hikes in Acadia National Park
• The Best Things to do in Acadia National Park
• How to see the sunrise at Cadillac Mountain in Acadia National Park
• Hiking the Precipice Trail at Acadia National Park
• How to backpack the Cutler Coast in Maine
• 7 Day Vermont Road Trip Itinerary
• 2-4 Day Acadia National Park Itineraries

About Portland, Maine

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Portland is the largest city in the state of Maine, with 40% of Maine’s residents living in the general area. But despite this, it still retains a small city feel, with historic buildings and no giant skyscrapers (the tallest building will soon be an 18 story building).  The city was established in 1786 and was originally the state capital of Maine, until Augusta took the title in 1832. Because of its location on the water, Portland became a booming center of trade, as it was the closest U.S. port to Europe. The city continued to grow when the railroad came to Portland in 1832, even overcoming a fire that destroyed much of the city in 1866, but around the 1960s, the area now known as Old Port began to deteriorate.

In the 1980s, the waterfront experienced a rebirth and today the Old Port neighborhood is one of the best preserved east coast historic waterfronts and has maintained much of its historic charm from the 1800s, with brick sidewalks and ornate buildings.  While the city itself is beautiful to look at, what we loved about Portland is that it has a little something for everyone. Whether you’re a fine dining foodie or prefer a good food truck (like us!), enjoy museums and art, love to walk around parks and experience history, or prefer to be out on the water, there is no shortage of things to do in Portland, Maine for any type of traveler.  

You can visit Portland, Maine year round, but your experience will vary depending on the season. Here’s a quick rundown of what to expect!

As you can imagine, winter is bitterly cold in Maine. The lows in December, January, and February are well below freezing, with highs barely above freezing. If you enjoy snow, there are lots of snow activities to partake in near the city, including skiing, plus some great coffee shops and bars to warm you up afterwards.  Note: Some activities and restaurants close in the winter, so you may not get the true Portland experience, but you will be able to see the city in a way many tourists do not and have less crowds.

The spring time will still be pretty cold, so you’ll want to pack layers for your visit, as the warmer temperatures don’t really come around until May. But the springtime will bring less crowds and flowers in bloom, with many outdoor activities becoming more accessible again. 

Summer is the best time to visit if you want the perfect weather and most activity options. You’ll have temperatures that rarely go above 80 and the lowest chances of rain all year. However,  this pleasant weather does bring the summer vacation crowds, so you’ll want to book activities and lodging early. There are also quite a few fun festivals and events in the summertime to enjoy!

If you’re looking for crisp, cool temperatures, fall foliage, slightly cheaper accommodations, and less crowds then fall is your season in Portland. We visited in the fall and LOVED it! Our visit was during mid to late October, around peak fall foliage time , and we were treated to sunny, warmer days. We may have just gotten lucky though, as typically October and November are rainier months, so make sure to bring a rain jacket and some layers just in case!

Portland is located in the southern part of Maine and is close to other major cities in New England and out East, which makes it pretty easy to get to no matter your mode of transportation. 

Flying to Portland, Maine

The closest airport to fly into will be the Portland International Jetport , which is located very close to downtown Portland and is Maine’s largest airport. It is served by several major airlines including American Airlines, Delta, jetBlue, Southwest, and United.  If the Portland airport doesn’t offer a good flight option for you, the Boston Logan International Airport (BOS) is about 2 hours away and is a massive airport that is serviced by all major airlines and offers nonstop flights from many destinations in the United States.

Driving to Portland, Maine

Driving to Portland instead? Here is how far the city is from nearby popular destinations:

• Boston, MA: 2 hours (112 miles)
• Providence, RI: 2.5 hours (163 miles)
• Bar Harbor, ME: 3 hours (175 miles)
• Acadia National Park: 3 hours (171 miles)
• Burlington, VT : 4 hours (257 miles)
• New York, NY: 5 hours (316 miles)
• Montreal, Quebec, CA: 5.5 hours (277 miles)
• Buffalo, NY: 8.5 hours (556 miles)

Note: These times are estimates based on no traffic, but plan to spend longer on the road. Also, some of the times above include driving tolls. If you want to avoid paying for tolls, make sure to turn off tolls on your Google Maps settings.

Getting around Portland, Maine

During our time in Portland, we did a combination of walking and driving to get around the city.  The Old Port area is very walkable, but to get between neighborhoods and to explore some of the spots a bit out of town, you’ll either need to drive or rent a car , take a Lyft/Uber, or take public transportation .  For Uber and Lyft, we’d highly recommend looking at their fare estimator tools ( Uber , Lyft ) to see how much you’d expect to spend when getting around town. While it would likely be affordable around town, it may get pricey to visit some of the spots outside of the downtown and main city area. We still think it would be cheaper than renting a car, but if you plan to explore more of Maine, having a car is worth it!

Where to park in downtown Portland

Since we were staying in our van while visiting Portland and were sleeping outside of town, we had to drive into town any time we wanted to explore. And while we mostly explored by foot once in town, we still had to find parking for our van. Our van is 22.5 feet long, so it’s longer than a normal vehicle, but we were able to find parking both times we drove into town. The first time was in the afternoon and we needed parking for about 5 hours, so we parked in this lot , which was $20 for all day parking. It was definitely pricier than street parking, but was a safe spot to leave the van. The second day we arrived in town very early and parked here at a meter, which only cost a few dollars for a few hours. It was a great spot! Note: RV parking (trailers or anything over 23 feet) is basically non-existent in the city, so if you have an RV, we suggest staying at a campground and either driving your vehicle or taking a Lyft around.

To truly experience Portland, we suggest staying in the downtown area, where you can walk to coffee shops, restaurants, and bars, as well as the waterfront. Below are some of our top suggestions for Airbnbs (our preferred way to stay when not in our van!) and hotels, all convenient to the best things to do in this Portland guide.

Hotels 

Portland has almost any hotel chain you can think of right in the downtown/Old Port area. 

• Hampton Inn Portland Downtown – Waterfront
• Canopy by Hilton Portland Waterfront
• Hyatt Place Portland – Old Port
• Hilton Garden Inn Portland Downtown Waterfront
• Courtyard by Marriott Portland Downtown Waterfront

Curious how we get FREE flights and hotels? Check out our list of our favorite travel cards that have saved us thousands of dollars!

Staying in an Airbnb would be a great way to experience the downtown/Old Port area of Portland like a local. East End, Walk to the Old Port (1 bedroom, 1 bathroom): This Airbnb is located in the charming East End area, which has a more neighborhood feel than Old Port, but is still close by to enjoy all of the popular sights. It also includes parking, which is a big perk! Bright & Spacious Apartment with Amazing Shower (1 bedroom, 1 bathroom): This bright and airy apartment is located on the western side of downtown, north of West End. It has all the amenities you’d need in an Airbnb stay including a washer and dryer and very nice bathroom and shower.  Extraordinary Architectural Masterpiece Downtown (1 bedroom, 1 bathroom): This beautiful penthouse rental is located on top of the Old Port area. You have great views of the surrounding area through the big windows and can even enjoy them outside in your own private courtyard. It has a fully stocked kitchen with a gas range, but is also walking distance from many of the delicious restaurants we mention in this guide. Quiet, Sunny 3 Br 2 Bath with Deck and Views (3 bedrooms, 2 bathrooms): This second floor rental can sleep up to 6, has beautiful bedrooms, and a deck with gorgeous views of the water, as well as a grill so you can cook and enjoy the outdoor space!

If you’re like us and traveling in a van or RV, here are some options close to Portland, but still a drive away.  Bayley’s Camping Resort   This campground is a 21 minute drive to Portland and has all the camping options you can think of. Along with loads of amenities, there is even live music on the weekends!  Saco / Old Orchard Beach KOA Holiday This KOA is also located about a 25 minute drive southwest of Portland and has all the camping amenities you’ll need.

Old Orchard Beach Campground This campground has 4 main areas with 3 of them being for campers and RVers. Reviewers say it is very clean, the staff is very friendly and is in a great location.

Boondocking

There aren’t very many boondocking spots in Portland, in nature or even in a parking lot. If you’re in a pinch or are just in for one night, the Falmouth Walmart allows overnight parking and the Freeport Village Station is a quiet place as well. We stayed at both of these and had a safe, quiet experience. 

Portland, Maine is what we like to call a “liveable city.” This is a title we give cities we visit that we could see ourselves living in and when visiting, you may spend a lot of time doing things that you would do at home, like visiting parks, going out to eat, checking out coffee shops or bars, and shopping. They may have tourist attractions, but the town doesn’t necessarily revolve around tourist sights and for the most part the things you do are relatively normal activities.  And what that means for us is that we could spend tons of time in these cities just hopping around to different restaurants, going for walks, and just enjoy “living” there. So while you could spend weeks in Portland just experiencing life like a local, for a tourist trying to visit the most popular sights, we suggest having 2-3 days. This timeframe will give you the chance to experience some of the best activities, explore the downtown area, plus try a handful of good restaurants. We’re including a two day Portland, Maine itinerary at the end of this guide to help you plan your time in the city!

Ready to explore the city? Below are some of the best things to do in Portland, Maine, based on our experience, as well as spots that were high on our list and highly recommended, but we ran out of time to visit. If you’re overwhelmed by all there is to do, we’re including a two day itinerary below as well!

Watch our time in Portland, Maine, including exploring the city and going lobstering !

Drink Local Coffee

The best way to start our day in a new city is with a local coffee shop! And lucky for us, Portland has no shortage of solid options. We LOVED Tandem Coffee Roasters while in Portland, which not only roasts their own coffee, but also makes breakfast biscuits that we hear are solid (arrive early to snag one). This coffee shop is located in a converted 1960s gas station and you know it’s good when locals are lined up before it even opens. Some other good coffee shops to check out are Bard Coffee , Yordprom , Speckled Ax , Burundi Star Coffee , Coffee By Design , Higher Grounds , and The Proper Cup .

Walk around Old Port

One of the best things to do in Portland, Maine is to just walk around the Old Port area, which goes from Commercial Street along the water up a few blocks. This area of Portland is extremely walkable and has so much of the historic charm we mentioned earlier in the guide.  While in Old Port you can check out the different shops and boutiques, enjoy the different restaurants (more on that next!), walk along the water, and maybe see fishermen loading and unloading their daily catch. You could spend a whole afternoon just in this area and likely not see it all!

Eat your way through the city!

Portland was named Bon Appetit’s 2018 Restaurant City of the Year and there is NO shortage of delicious restaurants to enjoy while in the city. In fact, where to eat will likely be the toughest decision you’ll have to make during your visit, as there are just so many incredible options.

Where we ate

During our visit we visited a couple spots that we highly recommend, plus a few that we were dying to try, but ran out of time for.  First up on our Portland food adventure we went to The Holy Donut for their famous Maine potato donuts, which have a unique texture from a regular donut, but are so hearty and delicious. We got three donuts total, including a Chocolate Sea Salt (this flavor is their most popular), Pumpkin Head, and Maple Bacon, which was hands down our favorite. They also have gluten free and vegan donuts too! We also ate at Bite Into Maine , which was said to have one of the best lobster rolls in town. We were torn between the Maine style, which is cold and is tossed in mayo and has chives on top, or the Connecticut style which is hot and has melted butter that they pour on top right in front of you. The Connecticut style sounded better to us, but we were in Maine afterall, so we had to try both. And to our surprise, they were both equally delicious and we couldn’t really pick a favorite. Both had incredibly tender lobster meat and were served on a heavenly, toasted New England style hot dog bun.  At the time of our visit, each roll (we got the 4.5 oz) was $26, which is pricey, but we had heard that lobster was more expensive in 2021 due to demand and that this was a pretty standard price. We typically do not spend that much on food, but it was more than worth it to try this decadent delicacy!  We also got a homemade Whoopie Pie from Bite Into Maine, which is Maine’s official state treat. It’s two chocolate cake-like rounds with a creamy filling between them and is said to have been popular in Maine since 1925. It was delicious! And we washed it all down with the state fruit of Maine, but in soda form, Blueberry soda.

Other spots to check out

While we wish we could’ve eaten more in Maine, our time constraints and budget didn’t allow it, but there were some spots that came highly recommended to us that are high on our list for next time and we feel confident recommending. Hifi Donuts for more traditional donuts, Standard Baking for delicious baked goods, Eventide Oyster Co. for oysters and other seafood, Duckfat for duck fat fries (they also have a frites shack in town), poutine, and sandwiches, The Highroller Lobster Co for lobster rolls and other lobster filled dishes, Terlingua for BBQ, and Hot Suppa for brunch. There are obviously many more amazing local restaurants than this, but those are the spots that are pretty iconic to check out if it’s your first visit. 

Go on a food tour!

Can’t decide where to eat and want to experience a taste of many spots? Go on a food tour! Maine Day Adventures offers food tours in both the Old Port and East Side neighborhoods!

Go Lobstering! 

When you think of Maine, the top food item that comes to mind is likely lobster (or lobstahh!) and our absolute favorite thing we did in Portland, Maine was go lobstering with Lucky Catch Cruises ! On this lobstering tour you go to not only get out on the water and learn about how lobsters are caught, but you also get hands-on experience, from baiting and emptying traps, measuring lobsters, banding claws, learning the difference between males and females, and so much more.  The crew really makes you feel like you’re a fisherman and puts you to work. It was one of the most fun and educational tours we have ever been on! (Watch our full experience here ) You can choose between different sailing locations and we did the Seal Watch tour, as it worked best with our schedule. We didn’t see any seals, but that didn’t matter, the views were still amazing and we were so focused and jazzed about catching lobsters! 

And at the end, you have the option to buy a lobster from the boat, which may be one that you just caught (don’t worry, they have extras from earlier cruises if you didn’t catch many, like our boat). You buy this lobster at market price (ours was $10) and then can take it over to Portland Lobster Company , where they’ll steam it and provide some sides, like fries, corn, and coleslaw for only $12. While we definitely preferred our lobster in roll form, it was so fun to catch lobsters and eat one fresh right afterwards!

Tip: make sure to bring cash to buy a lobster AND for a tip!

• Take a ferry to Peaks Island

Want to visit an island while in Portland? Take a ferry to Peaks Island , which is just a 17 minute ride away on the Casco Bay Ferry . While on the island you can walk around, kayak, rent bikes or a golf cart , and enjoy a couple public beaches. It’s a calm, relaxing getaway from the “big” city!

Visit the Portland Observatory

The Portland Observatory , which is located on the east side of town, is a historic maritime signal station and is the only one left in the United States! It was created in 1807 by order of Captain Lemuel Moody as a way to alert ship owners of their ships arriving, as you couldn’t see the ships entering the harbor until they were almost there.  Moody charged a fee of $5 per year for ship owners to be alerted of their ships and used a telescope to identify vessels as far as 30 miles away. This maritime signal station ran until 1923, when two-way radios replaced its purpose. It has been renovated multiple times and is now open to the public to experience and costs $10 per adult for tours. Unfortunately this spot was closed during our visit, but we would love to check it out next time!

Kayak to Fort Gorges

During our cruise with Lucky Catch Cruises, we went by this cool looking fort on an island on the Casco Bay called Fort Gorges . This fort was built in 1864 to protect Portland from foreign naval powers, but by the time it was completed, new technologies for artillery had emerged and it was already obsolete. It ended up being a storage facility in both World Wars and was then given to the city of Portland. The only way to access this fort is by boat or kayak, which limits how many people actually get to experience it. If you don’t have your own method to get out there, we suggest going on a tour with Portland Paddle , who will ensure you cross the Casco Bay safely and take you all around the fort. It is worth noting that the fort isn’t maintained very well, so it provides a very dark, rustic experience, which in our opinion, only makes it more fun and authentic to check out! 

Explore Fort Williams Park & the Portland Head Light

Another huge highlight for us in Portland was Fort Williams Park , which is a free park that was formerly a military fort. Construction of the fort began in 1873 and the fort became officially named Fort Williams in 1899. During World War 1 the fort was manned by artillery companies and National Guard troops and during WWII it served as the headquarters of the Harbor Defenses of Portland, before becoming more of a training site in 1951. Today there are a couple batteries to check out, an old mansion , and one of the most iconic lighthouses in the US, called the Portland Head Light . This lighthouse was the first lighthouse completed and put into service by the government under the Lighthouse Act of 1789. 

It was first lit in 1791, using 16 whale oil lamps. The tower and keeper’s quarters have changed a bit over time and the tower now stands at 80 ft tall. And it is said to be the most photographed lighthouse in America, and also the oldest in Maine. Tip: If you want to check out more lighthouses, Bug Light and the Spring Point Ledge Lighthouse are close by too! Another perk of Fort Williams Park is that Bite Into Maine is located here, so you can enjoy history, views, and lobster rolls all in one spot!

Walk the Eastern Promenade

Located on the East Side of town is the Eastern Promenade , which is Portland’s largest developed park. Here you can walk the 2 mile trail that goes along the Casco Bay waterfront, hang out at a beach, and just soak up the views. If you’re looking for a nice, scenic stroll, this is a great stop!

Visit the Victoria Mansion

For architecture lovers, check out the Victoria Mansion , also known as the Morse-Libby House. This home is a perfect example of a 19th century Italian Villa style home, with a gorgeous exterior and interior to explore, with 90% of the interior being original. It was built as a summer home for Ruggles Sylvester Morse and his wife and completed in 1860. Once Ruggles died, his wife Olive sold the home to J.R. Libby, who kept it in almost the exact same condition and lived in the home until 1929.  The house has been a public museum since 1941 and costs $16 per adult, with different rates for seniors, children, students, and families.

Go Brewery Hopping

Portland is home to an amazing craft brewery scene and while we don’t drink, if you do, you’ll be in beer heaven! Here are some top breweries in town:

• Allagash Brewing Company
• Bissell Brothers Brewing Company
• Oxbow Blending & Bottling
• Foundation Brewing Company
• Austin Street Brewery
• Rising Tide Brewing Company
• Belleflower Brewing Company
• Lone Pine Brewing Company
• Fore River Brewing Company

If you want a safe way to check out multiple breweries around town and not worry about driving, go on a brewery tour with Maine Brews Cruise !

Check out the Portland Arts District & Museums

Portland is home to an arts district, which is located around Congress and High Streets and was created in 1995 to be the cultural and creative hub of the city, with different galleries.  The Portland Museum of Art is the most popular attraction in this area and focuses on a mission called “Art for All,” which was created to ensure the museum is diverse, inclusive, and accessible for all. There are changing exhibits, as well as permanent collections to explore while in the museum. It costs $18 per adult (22 and up), $15 for seniors and students over 22 years old, and is FREE for anyone 21 or under. If you visit the Arts District on the first Friday of the month you can take part in the First Friday Art Walk . During this event, all of the art institutions in the Arts District open their doors for free from 5 PM to 8 PM.

Now that you know of some of the best things to do in Portland, Maine, here is our suggestion of how to combine some of these activities into two epic days in the city! While you won’t be able to see and eat it all in two days, these are our top suggestions to ensure you experience the best of Portland.

• Grab coffee at Tandem Coffee Roasters and then donuts at The Holy Donut.
• Lobstering cruise with Lucky Catch Cruises (our TOP PICK!) and then enjoy steamed lobster at Portland Lobster Co.
• Kayak to Fort Gorges 
• Go on a food or brewery tour
• Visit the Portland Art Museum or Victoria Mansion.
• Enjoy the rest of the day by walking around the Old Port area, going into different shops.
• For dinner, head to Eventide. We suggest trying to make a reservation in advance!

• Start the day with breakfast at Hot Suppa or grab a pastry at Standard Baking. 
• Head to Fort Williams Park for the morning and afternoon. Explore the bunkers, outside of the mansion, and the Portland Head Light!
• Have lobster rolls and whoopie pies at Bite Into Maine.
• Spend the rest of the day doing any activities from day one that you didn’t have time for, or go up in the Portland Observatory and walk around the Eastern Promenade.
• Enjoy your final meal at Duckfat or Terlingua.

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One Day in Portland, ME - Travel Itinerary

Much like its west coast counterpart, Portland, Maine offers up an abundance of outstanding coffee, local breweries, and delicious eateries as well as a plethora of outdoor activities. We had the privilege of visiting Portland, ME in our travels to all 50 states and absolutely fell in love! There’s just something about a historic, New England coastal town that just can’t be beat. Even in our short, one day visit, it was easy to see why people return to this beautiful small city time after time. If you’re a time-crunched traveler like us, then you want to get the most out of your time in a city, so we put together this one day itinerary for what we think is the perfect day in Portland!

*Be sure to check out our “One Day in Portland” travel vlog for a closer look at our visit!

Now, let’s get into it…

9:00am: Coffee/Breakfast

Holy Donut (various locations but we went to the 194 Park Ave location)

Home of the famous Maine Potato Donut, The Holy Donut makes delicious craft donuts with all-natural ingredients. And yes, they actually use potatoes in their donuts! It’s what makes them so moist and delicious!

Tandem Coffee Roasters (742 Congress St)

Coffee By Design (recommended location: 620 Congress St)

Bard Coffee (185 Middle St)

Speckled Ax (567 Congress St)

10:00am: Explore the Working Waterfront and the Old Port

Lincoln Park (green space)

Sea Bags Flagship Store (recycled sails turned into bags)

Portland Dry Goods (clothing and accessories)

Portland Trading Co. (clothing and accessories)

Something's Fishy (gift shop - 32 Exchange St #5020 )

Shipwreck & Cargo (gift shop)

12:30pm: Lunch

Luke’s Lobsters (60 Portland Pier… where we went)

Famous for, you guessed it… Lobster! But really, you can’t go wrong with anything here. Seafood doesn’t get much fresher than this! Luke’s has become a worldwide seafood shain/supplier at this point, but its roots are in the northeast, and all of their lobster is sourced right from the coast of Maine!

Becky’s Diner (390 Commercial St)

High Roller Lobster Co. (104 Exchange St)

Duckfat (43 Middle St)

2:00pm: Self Guided Lighthouse Tour

No trip to the New England coast would be complete without checking out some lighthouses, so take some time to head out to any or all 6 of the incredible lighthouses within a short 15 minute drive of the city!

Portland Head Light (12 Captain Strout Cir, Cape Elizabeth, ME)

Ram Island Light (view from Portland Head Light)

Two Lights State Park (7 Tower Dr, Cape Elizabeth, ME)

Portland Breakwater Lighthouse, AKA Bug Light (S Portland Greenbelt Pathway, South Portland, ME)

Spring Point Ledge Light (2 Fort Rd, South Portland, ME)

5:00pm: Sunset Cruise (times vary based on the time of year you’re visiting)

Rocky Bottom Fisheries (60 Portland Pier… where we went)

What better place to watch the sunset over the Portland Skyline and nearby lighthouses than on a lobster boat in Casco Bay with an ice cold drink in your hand? The answer… Nothing! Just remember, it’s BYOB! If you’re looking for something local, check out Allagash Brewing Company, Austin Street Brewery, or Banded Brewing Co.! And if you’re short on time like we were, you can just swing by a convenience store, because many of them carry local brews! We really enjoyed the Allagash White which is a Belgian-Style Wheat Beer.

Portland Schooner (56 Commercial Street)

Lucky Catch Cruises *Sunset Lobstering and Island Lobster Bake included* (170 Commercial St)

7:00pm: Dinner

Portland Lobster Co. (180 Commercial S… where we went)

This is THE place to be for an amazing, casual dinner on the water. Voted the “Best Lobster Roll in Portland”, “Best Waterfront Dining in Portland”, “Best Patio/Deck in Portland”, AND “Best Music Venue in Portland”, Portland Lobster Co. has it all and shouldn’t be missed!

J's Oyster (5 Portland Pier)

DiMillo's On The Water (25 Long Wharf)

Eventide Oyster Company (86 Middle St)

We hope that these tips help you plan your visit and make the most of your time in Portland! If you did find it helpful, please consider heading over to our YouTube Channel and subscribing for more travel content and following us on Instagram , it would mean the world to us!

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3 Days in Portland, Maine Itinerary | A Long Weekend Guide + Map

Nov 13, 2023

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Portland, Maine, is a city brimming with coastal flair, historic buildings, and the small-town charm worthy of an epic New England getaway.

This port city is dotted with excellent eateries and bars, as well as art galleries on every corner, and gives you easy access to southern Maine beaches and state parks.

A long weekend in Portland, Maine, is nothing short of a foodie and adventurer’s dream.

Between the fresh produce markets, the picturesque lighthouses, and the most delicious lobster in the U.S., you may want to stay longer.

In this guide, I unpack the best ways to explore this charming city through an extensive Portland, Maine weekend getaway 3-day itinerary.

Now without further ado, let’s dive into the ultimate Portland, Maine, weekend trip.

Tip: If you don’t have three days, explore the town’s highlights on a day trip to Portland, Maine .

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Disclaimer: Hey explorer! This post contains affiliate links which means I earn a small percentage of each purchase made through my links. I only ever recommend products I believe in and appreciate your support if you decide to use my links—thank you!

Your Portland, Maine Weekend Trip At A Glance + Map

Coffee + breakfast, cruise or mailboat to casco bay, walk from commercial street to old port, lunch at little tap house, portland observatory tour, join the first friday art walk, dinner on the waterfront.

• Coffee on Congress Street
• Stroll through the Portland Farmers Market at Deering Oaks Park

Go on a Lobstering Tour

Catch a ferry to bug light park + lunch, beer tour + dinner, coffee + donuts, visit friends of the kotzschmar organ, peruse portland, maine’s bookstores + lunch, head to the eastern promenade + dinner.

Here is a map you can use on your trip.

Click here for a live version of the map !

Read Next: The Best Camera Gear for Travelers

Day 1 in Portland

Everyone knows a good adventure starts with a delicious cup of coffee and a tasty breakfast.

Portland, Maine is abundant with quaint coffee shops; one chain that you’ll find dotted across the city is Coffee by Design.

Try the one on Diamond Street, where you’ll discover an artisan roastery, coffeehouse, and cupping room.

On Franklin Street, there’s Coffee ME UP, where you can enjoy your specialty coffee beverage with a selection of light pastries, sandwiches, and tasty smoothies.

Once you’re pumped on caffeine, hop on the first ferry to Casco Bay.

You can catch a gorgeous sunrise via a cruise or a mailboat run at 10 am.

And in case you’re wondering, yes, a mailboat is exactly what you think it is — a boat delivering mail to the island.

Locals enjoy commuting to Casco Bay via a mailboat.

The daily runs from Portland, Maine, cost $17 per adult, take about 2.5 to 3.5 hours, and stop at five islands. This should be enough time to explore your chosen destination. 

Wanderer Tip: If a cruise is more your style, charter a tall schooner ship tour and sail the rugged Casco Bay coastline, catching sights of lighthouses, seals, and other coastal wildlife.

Upon returning to the mainland, stroll down Commercial Street, and discover some of the best spots in Portland, Maine.

Walk along the working waterfront with fishing boats, lobster spots, jewelry, and pottery shops.

Take some time to explore the historic tourist district and learn more about Portland through guided walking tours to Old Port.

You can browse through cute boutiques, art galleries, restaurants, and bookshops.

The charming bookshops range from family-owned stores with a dog-friendly atmosphere selling works by local artists to book shops where you can grab a snack, a coffee, or a beer.

After all that walking, you must be famished.

Head down to  Little Tap House on High Street from Old Port for local delights. The farm-to-table gastropub serves scratch-kitchen cuisine — the fish and chips are delicious and generously portioned.

Wash your meal down with a refreshing cocktail, a light wine, or a mimosa. Ready for your next attraction? That’s great because it’s right across the street.

 A skip away from Little Tap House, you’ll stumble upon the Portland Observatory.

The maritime signal tower is the country’s only surviving one of its kind.

From atop the tower, you’ll see stunning views of Casco Bay. Walk a little further, and behold the Portland Museum of Art.

Take a tour of the museum’s extensive collection and varying displays of contemporary art and film, then head over for some photo snapping at the outdoor sculpture park.

Is it Friday? Then you know what to do in Portland, ME.

Enjoy strolling through the city’s galleries, alternative art studios, and museums, as well as vibing to live music at Congress Square Park.

This art walk also boasts paths lined with pop-ups, coffee shops, jewelry, and pottery vendors.

The event happens every first Friday of the month, and doors open from 5 pm to 8 pm. Oh, and did I mention the entrance is absolutely free?

Portland, Maine’s waterfront is buzzing with fantastic eateries, bars, and bistros.

You’ll be spoiled for choice between the hand-crafted meal on Fore Street, and Boone’s Fish House & Oyster Room—their lobster mac n cheese is delightful.

Boone’s is quite a popular spot attracting large crowds and a lively atmosphere. 

Day 2 in Portland

Coffee on congress street .

Kickstart day two of your weekend trip to Portland, Maine, with a fresh caffeine brew on Congress Street.

If you’re in the mood for a casual vibe and a fresh sandwich made at the counter, Yordprom Coffee Shop is the perfect spot for you.

For a more modern aesthetic, Tandem Coffee and Bakery take the cup. Their freshly baked pastries are excellent, and the chai latte may be the best you’ve ever had.

Stroll through Portland Farmers Market at Deering Oaks Park

Shop from Maine’s top farmers and food producers in one stop, surrounded by gorgeous green spaces and expansive water fountains. 

The farmers’ market is open for the summer season on Wednesdays and Sundays from 7 am to 1 pm, May through November.

And in the wintertime, it’s open Sundays from 9 am to 1 pm, December through April, at the Maine Girls Academy gymnasium.

One thing you must do when in town, even if you’re only spending one day in Portland, Maine, is going lobstering! 

There are plenty of tour providers along the shore. You’ll find Lucky Catch Cruises and Rocky Bottom Fisheries.

Not only do you see the catching process, but you also get to help with measuring the lobster and emptying the traps.

Tip: If all that lobstering gets you hungry, why not join a seafood and lobster walking tour and sample some of Portland, Maine’s favorite local delicacies?

Kickback and relax to stunning skyline views and gorgeous Portland Harbor vistas at this nine-acre manicured parkland.

Home to the picturesque Portland Breakwater Lighthouse, Bug Light Park is the perfect place to kill time before the next adventure begins.

If you like, you can pack a picnic basket and enjoy a tranquil lunch on the lawn. Or opt for a gourmet lunch at one of South Portland’s famous eateries.

North 43 Bistro serves classic American cuisine, like smash burgers, and has excellent marina views.

For seafood delights, stop by Saltwater Grille for an upscale ambiance and Portland skyline views.

Other things you can get up to at Bug Light Park include biking, saltwater fishing, and boating.

Take a three-hour South Portland bicycle tour and explore four gorgeous lighthouses.

This includes the Portland Head Light, one of the most photographed landmarks in the city. Its white façade contrasts the rocky shores surrounding it and the azure backdrops of the sea and sky.

Nature lovers will appreciate walking the half-mile-long beautifully landscaped Cliff Walk to get to the lighthouse.

Portland, Maine, has the second most breweries per capita in the U.S. after Vermont. 20 breweries and over 700,000 people — now that’s a lot of beer!

It goes without saying that you won’t see all these breweries in one go, so choose the one that serves grub of equal standard.

Some of the best breweries in Portland, Maine, for a seating experience, include Foulmouthed Brewing and Foundation Brewing, with an expansive variety of crafts from sour ales and farmhouse ales to IPAs and porters.

For a mobile beer experience, join a Maine Brews Cruise tour and enjoy delicious craft beer on a biking tour, beer bus, or walk from one spot to another. 

Day 3 in Portland

A trip to Portland, Maine, is incomplete without tasting the city’s delicious desserts.

Donuts are popular, and there’s nothing wrong with a little sugar rush to start your last day in Portland. 

Try the tasty donut holes at The Cookie Jar in South Portland, or opt for a creative donut made with locally sourced potatoes at the famous Holy Donut on Commercial Street.

The Holy Donut also serves gluten-free and vegan options.

The Kotzschmar Organ is one of only two municipal organs in the U.S., a true Portland hidden gem.

You can see this colossus by either touring or attending a concert at Merrill Auditorium in the City Hall.

Thanks to the Friends of the Kotzschmar Organ organization, the instrument is still in use, and if you’re lucky, you may catch the annual classic — The Phantom of the Opera .

While Portland, Maine, is often hailed for its lobster rolls and craft breweries, one industry that bears mentioning is the town’s vibrant literary scene. 

The city has about 13 independent bookstores, selling every kind of new, used, and comic book you could possibly imagine.

Check out some interesting spaces like Longfellow Books, Sherman’s, and the cozy Print: A Bookstore.

For lunch, stop by LB Kitchen for something refreshing and healthy to munch on. The bright and colorful eatery serves delicious lunch bowls, salads, and creative smoothies.

The Eastern Promenade is a 68-acre green space on Munjoy Hill designed by the Olmsted Brothers landscape firm, also renowned for creating New York’s Central Park and the Boston Commons.

This expansive lush space offers the best picnic spots and a two-mile scenic hiking and walking trail in Portland, Maine. Catch the kaleidoscopic sunset or kick back on the beach.

The Eastern Promenade is also great for starting your Portland, Maine, day trip to Acadia National Park .

But if you’re running short on time, a hearty dinner and wine at a nearby eatery will do just fine.

Check out Jing Yan for a unique Asian experience. The Front Room and Blue Spoon offer classic American fare and tasty craft beverages.

Where To Stay in Portland, Maine

Now one thing you don’t want to skimp on during your Portland, Maine getaway is the accommodation. The best area to call home is undoubtedly the Downtown / Old Port district.

This part of town is where you’ll find an abundance of luxury chain hotels and budget-friendly Airbnb.

You’ll also be in the heart of the city, allowing you to walk to nearby restaurants, art galleries, and local breweries.

Some places to consider include:

The Press Hotel, Autograph Collection — Embrace the New England atmosphere at this elegance-inspired boutique hotel in the Portland Downtown Historic District. Not forgetting the chic on-site restaurant, where you can enjoy tasty seafood and wine pairings.

Canopy By Hilton Portland Waterfront — If you like shabby chic and contemporary decor with a touch of wooden oak furnishings, this is the hotel for you. Canopy is home to Luna Rooftop Bar, serving great cocktails and waterfront views thanks to its accordion glass walls.

Aloft Portland, Maine — Funky and colorful; and the art-deco furnishings make Aloft one of the best hotels in Portland, Maine. Spend some downtime riding bikes along the waterfront, playing billiards, or cocktailing it up at WXYZ Bar.

Getting Around

Portland, Maine, has sophisticated transportation methods ranging from buses and taxis to ferries and trains.

But the best way to explore the city is by walking or biking along the cobblestone streets downtown and the waterfront.

List of Things To Do in Portland, Maine

Here’s a quick roundup of Portland, Maine’s best things to do. These top attractions and activities make a great addition to your New England road trip . 

Walk Around Old Port — Discover the historical buildings, quaint bookshops, and charming eateries dotted across the Old Port. See the city’s iconic landmarks, from the bustling Commercial Street to the scenic waterfront.

Visit the Portland Observatory — This 86-foot tall octagonal tower is one of Portland, Maine’s trademarks, with excellent cityscape views.

Tour the Portland Museum of Art — Within a two-minute walk from the observatory, you’ll stumble upon Maine’s largest and oldest public art institution.

Stroll Through the Portland Farmers Market — Buy everything from Portland’s local farmers, from fresh produce and baked goods to meats, jams, and sauces.

Explore Casco Bay via a Mail Boat — Enjoy the locals’ favorite way of experiencing Casco Bay via a mailboat run.

Take a Craft Beer Tour Through the City — If there’s one thing you’ll find scattered across Portland, Maine, it’s breweries. There are over 32 breweries for you to choose from.

Walk or Bike Along the Eastern Promenade — Catch the most stunning views of Casco Bay and Portland Harbor.

Marvel at the Portland Head Light — This historical lighthouse along the shores of Fort Williams Park in Cape Elizabeth has spectacular ocean and rocky Maine coastline views.

Enjoy a Picnic at Bug Light Park — Pack a picnic basket, grab an exciting book, and relax on the vast grassy lawn facing the city at this charming park.

Join the First Friday Art Walk — The first Friday of each month belongs to the arts in Portland, Maine, no matter the weather.

Go Bookshop Hopping — If you’re a book lover, the independent bookstore scene in Portland is really something you should take a gander at.

Hop on a Ferry to Peaks Island — Get unparalleled ocean views from Casco’s most populous island. Peaks Island is home to stunning public beaches, art galleries, and museums like the quirky Umbrella Cover Museum.

Go on a Lobstering Tour — Portland, Maine, is synonymous with lobster — lobster bisque, lobster rolls, or an authentic lobster bake. If you’re interested in seeing where the lobster comes from, why not join a lobstering tour?

Hop on a Lighthouse Trolley Tour — Spot Portland’s beautiful lighthouses, from the picturesque Spring Point Ledge Lighthouse to the famous Portland Head Light.

Admire the Kotzschmar Organ — Go off the beaten path and marvel at this gorgeous instrument with over 7,000 pipes.

Portland, Maine Itinerary 3 Days | Wrapped Up

Well, there you have it — 3 days in Maine’s largest and most vibrant city. Visiting Portland, Maine, is a must-add to any foodie’s and adventurer’s bucket list. 

From stunning waterfront views and historical landmarks to scores of quaint bookshops, breweries, and the tastiest lobster rolls in the U.S., you’re set to have a wonderful time.

And if you only have a day in Portland, Maine, explore the city’s highlights via a quirky, vintage fire truck tour .

So what are you waiting for? Pack your bags, book your stay, and gear up to have a fantastic time exploring and eating your way through Portland, Maine.

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I'm a burrito loving explorer who got fired from corporate America and turned that into my dream career as a photographer and blogger. Now I'm here to help you explore life's magic. Thanks for stopping by!

How to Spend Three Days in Portland, Maine

A trip to Portland, Maine, delivers more than just outstanding seafood and the best lobster in the US. Its fresh food is matched by the collection of breweries that you could spend all weekend visiting. Add in some fantastic galleries and fascinating museums and you have a recipe for a memorable 3 days. 

The population of just 66,000 allows Portland to provide bustling city vibe without diminishing its quintessential New England feel. Outside of restaurants and breweries, Portland maintains an old-time feel when everywhere is the world is in such a hurry to jump into the future. From rain-soaked cobblestone streets to classic independent bookstores, each day in Portland is the perfect chance to walk back in time.

Where to Stay in Portland, Maine

The best area to base yourself during your 3-days in Portland is within the Old Port district. Old Port mixes in with the downtown area providing excellent dinning and multiple breweries within walking distance, along with the starting point for many activities in this itinerary.

Most importantly, these walks will include venturing along the cobblestone streets, passing old bookstores and boutiques. 

The Best Time of Year to Visit Portland

Temperatures in Portland remain quite mild throughout the year, even in winter when the sprawling peninsula protects the city from the unrelenting Atlantic Ocean. Having said that, to truly enjoy what Portland is all about, it’s best to avoid the city during the winter months. 

For those that enjoy parks from blooming flowers all the way to auburn leaves, the Spring and Fall present the perfect opportunity to explore Portland. Museums and restaurants, closed in the winter, open their doors in Spring. While whale watching season begins in April.

Summers in Portland are wonderfully mild thanks to the ocean breeze floating in off the coast. The Summer is the best time to explore the beaches, to sail in Casco Bay and go sightseeing, including venturing to Acadia National Park.

Ok, now it’s time to for the fun part, the planning. With the help of this 3-day itinerary for Portland, you will be able to explore the city like a local, visiting the best museums and eating at all the tastiest restaurants. Let’s get to it!

Day One: Breweries and Books

Aside from being a lobster-lover’s paradise and a town of classic lighthouses, Portland has a thriving brewery scene that grows by the year. Since you have just the long weekend to spend in this coastal town, there is no time to waste.

If you have access to a car, it is easy to drive around Portland and into neighboring towns hitting up the best local breweries. These include the Bissel Brothers Brewing Company and the much-loved Allagash Brewery .

But since this is a fun vacation, why not take a load off your shoulders and join a Maine Brews Cruise ? With a variety of tours to choose from, you can experience Portland’s best breweries on foot with a friendly, knowledgeable guide. Or you can take to the high seas and explore local forts while getting your craft beer fix along the way. 

However, if you are traveling with friends or have a rather rowdy family, you might be tempted to experience the Baycycle Brews Cruise, a human-powered pontoon boat. Drink and pedal your way around Casco Bay, spending time with your favorite people while sipping on Maine’s best beers.

After lunch, provided you aren’t in need of a long nap and some Gatorade, walk it off by exploring the stunning cobblestone streets in Portland’s Old Port. Here you will find narrow roads flanked with gorgeous old brick buildings now home to a variety of cute boutiques, art galleries, restaurants and bars. If you have your tourist hat on, you will also wander by some shops that sell hand crafted souvenirs and trinkets to bring home. 

Begin on Commercial Street where you can sit by the waterfront and take in the views of the harbor and the boats running in and out. Once you’ve taken your obligatory photos, start your stroll down to Exchange Street, the most happening part of town. 

Despite growing popularity and tourism, Portland remains much the same and, in its own unique way, continues to pay homage to the city’s humble beginnings. A prominent example of this is Portland’s slew of old-timey book stores hidden behind red brick facades. 

In a world that runs full-steam ahead into the digital age, Portland’s wonderful literary scene holds on tight to its envious total of 13 independent bookstores. If you only have time for one, then make a beeline for Sherman’s , a longstanding Portland institution that opened in 1886. It houses an expansive section dedicated purely to authors from Maine. 

Although if you have a means of transport, Quills Books and Beverage combine all things great. Come check out their cafe, lounge and bar so you can read a classic with a coffee or a red wine in hand. 

Once dinner is sorted and you have tried some of Portland’s specialty dishes, it is time to explore the city’s nightlife. Portland’s many breweries and age-old pubs may not be the spot for a raucous Miami -style evening, but they make for a wonderful place to hang with friends and family.

For some fun live music, be sure to check out Blue , which specializes in Irish and Jazz tunes, a great complement to a few craft beers. Then there is Maps , which, as you probably guessed, has walls covered in various maps of the world. But to have a grand old time, then walk back down to Old Port where you will find Oasis , crammed into the district’s cobblestone streets. 

With an upstairs nightclub with a rotation of DJs, and several live acts each week, you can dance the night away right here. 

Where to Eat on Your First Day in Portland

For a light lunch after a big trip on the paddling pontoon boat, head to Banh Appetit , a new but welcome part of Portland’s impressive food scene. Serving authentic, handmade Vietnamese cuisine, Banh Appetit is a favorite among locals and those traveling through town. Begin with the cha gio (egg rolls) and end with the bo xao banh mi, which includes a delectable filling of lemongrass beef. Don’t forget to wash it all down with their limeaide, made fresh on-site.

For your first night in Portland, you will have an abundance of choice that particularly favors those that love their seafood. Even if you aren’t a big fan, Portland, being right on the fresh Atlantic Ocean, does it better than most. So for dinner, make a reservation at Eventide Oyster Co, where you can try Portland’s favorite lobster roll which comes in a doughy steamed bun topped with chives. 

Day 2: Museums and Islands

After a delicious breakfast to begin the day, make your way down to the Portland Museum of Art . On Congress Street, the museum houses an expansive collection of American, international and contemporary art. All up, there are over 22,000 pieces of art which date as far back as the 18 th century. Along the Museum of Art’s permanent collection, you will find a thorough rotation of exciting exhibits focusing on talented located artists and prominent works from all corners of the globe. If you are visiting on a Friday, the good news is that entry is free from 10am to 8pm!

Once you have your art fix, continue down Congress Street to the Maine Historical Society Museum . The Historical Society helps to preserve and celebrate over 12 centuries of life in Maine. Inside you will find a fantastic gallery with artifacts and rotating exhibits along with the Wadsworth Longfellow House, which is listed on the National Register of Historical Places. You can take a tour of the iconic poet’s boyhood home or download a self-paced audio tour. Afterwards, hang out in the gorgeous garden and relax under the warm Maine sun. 

Although we have listed a great lunch option below, consider getting it to-go or picking up some supplies for a classic Portland picnic. We know just the place for you to kick back with your partner or friends and family and enjoy a peaceful afternoon. 

With your picnic supplies and a cheeky bottle of bubbly, make your way down to the Eastern Promenade. Designed by the same firm who created New York’s iconic Central Park, the Eastern Promenade is 68 acres of lush green landscape with playgrounds, sports fields and a plethora of casual walking paths. 

On one of the rolling hills, sit back and enjoy the expansive views of Casco Bay and downtown Portland. Once the lunch is complete, stretch your legs out on the 2 mile long walking path that will have you very excited for your next activity: the Casco Bay Lines Mail Boat .

There is no better way to explore the many islands of Casco Bay that by jumping onboard a working boat that carries mail and freight alongside its many passengers. A single ticket gets you up to a three-hour journey through the bay where you can hope on and off a variety of islands, the most popular destinations being Little and Great Diamond, Chebeague and Peaks Island. 

Peaks Island is a part of Portland and comes with a decent residential population that booms in the summer. With amazing ocean views to explore, you can get around the island on the preferred method of transport, the golf cart. 

For a quick energizer, head to Peaks Cafe for the much-loved cinnamon buns before making your way to the Backshore or the top of Battery Steele for the best views on the island. From there, hop back on the boat and continue island hopping into the late afternoon. 

An Alternative for Day Two

Anytime spent in Portland, Maine is a chance to explore one of America’s best national parks. Located three hours out of Portland is Acadia National Park, where you will find incredible hiking to thrilling peaks and stark cliff faces. The ‘Crown Jewel’ of the north Atlantic Coast is also home to uninhabited islands, and well-preserved estuaries featuring migratory birds and unique habitats.

One of the best ways to explore the park is by driving the stunning Park Loop Road through Mount Desert Island. This picturesque byway also takes you to some of the best spots in the park, including Cadillac Mountain, one of the first places in the USA to view the daily sunrise. 

A trip to Acadia isn’t complete without visiting Thunder Hole. Despite the crowds, it is well worth the visit, just the hear the monstrous thunder clap noise created by the waves breaking into the hole.

Finish your trip in beautiful Bar Harbor, a colorful town right on the park’s boundary. This is a great place to load up on hiking food or the place to enjoy dinner after the day’s adventures. For a special evening, check out Reel Pizza Cinerama , for an outdoor cinema experience matched only by the pizza.

Read More: Why Acadia is My Favourite National Park ; How to Spend a Perfect Three Days in Acadia National Park, Maine

Where to Eat on Day Two

Begin day two with a bang at Hot Suppa . With a lively breakfast atmosphere, a hybrid outdoor space and fantastic coffee, this is the best spot for breakfast in town. Chow down on your hearty southern cuisine that comes with a strong twist of New England personality, while the colorful walls create a vibrant diner experience. 

When lunch time comes around, load up at one of Portland’s trendiest restaurants, Black Cow. Half-cocktail bar, half burger-haunt, Black Cow is all about handmade burgers and craft cocktails. Choose from a variety of mouthwatering burgers and be sure to add a side of their special mac ‘n’ cheese. Complete your experience with a classic milkshake or hand crafted soda. 

For dinner, enjoy a night of farm-to-table dining at Fore Street . With locally sourced ingredients and hand crafted meals, Fore Street cooks up all your favorites with a typical Portland twist. The menu rotates daily, reflecting what is available locally, but they always hit the spot. 

Day 3: Whales and Beaches

Your day three itinerary for Portland, Maine will take you away from the historic downtown and further out to sea. Whale’s flock to Maine’s rich ecosystem full of sand eels, copepods, and plankton. From mid-April all the way to October, you will have the chance to see whales at their best before they swim south to warmer waters.

Whale watching is more than just a spectator sport, it is a fantastic way to connect with nature. Spotting the world’s largest living creatures off the coast of Portland is an inspiring sight, one that you won’t soon forget. 

While you can spot humpback, pilot, minke and the enormous finback whales from the comfort of the Portland shoreline, you can’t beat being out on the water among all the action. 

With Odyssey Whale Watch , you will join a cruise with almost a decade of experience. Both fun and educational, this adventure is great for young and old. Enjoy the invigorating nature, fresh ocean air and entertaining narration as you go search for these impressive beasts. Half-day tours begin at 10am and 2.30pm, lasting around 4 hours each.

If you arrive out of whale watching season or don’t feel like venturing out to sea, sign up for a walking food tour and round out your culinary experience in Portland. This tour will cover all the hotspots you may have missed, along with providing local insight into hidden gems that don’t show up on a Google search.

Over two-and-a-half hours, you will eat your way around the historic Old Port, sampling multiple restaurants serving anything from seafood to Italian. 

Where to Eat on Day Three

Tandem Coffee may not look like your typical breakfast joint, it is within an old gas station after all. However, this cute coffee and bakery establishment serves up enlivening coffee and some of the best pastries in the region. The home-made biscuits will melt your heart and their signature breakfast sandwiches features these biscuits with an envious mix of butter, sweet & savory flavors that will have you drooling for the rest of the day.

If you aren’t out in search of whales or traipsing over town on your food tour, then stop by Saltwater Grille for your last meal in Portland. With an amazing view to accompany your selection of delicious seafood, chowder and vegetarian options, this will be a heart-warming way to end your travels. 

Final Thoughts on Portland, Maine

Portland, Maine offers an exciting mix of throwback architecture and relaxing culture along with their fresh dining scene and thriving collection of breweries.

Being stuck between a large town and a small city is in no way a disparaging remark, as Portland provides visitors with all the impressive aspects of big city living with a hometown feel along with being very walkable.

Overall, this three days in Portland itinerary will have you falling in love with the town and quickly planning a return adventure. 

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Lauren Juliff is a published author and travel expert who founded Never Ending Footsteps in 2011. She has spent over 12 years travelling the world, sharing in-depth advice from more than 100 countries across six continents. Lauren's travel advice has been featured in publications like the BBC, Wall Street Journal, USA Today, and Cosmopolitan, and her work is read by 200,000 readers each month. Her travel memoir can be found in bookstores across the planet.

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I would love to visit Portland! It sounds like a great place to visit.

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Portland Maine Itinerary – 3 Days

Portland, the Goldilocks of cities. It’s not too big, not too small & has jussst the right food and active adventures. If you haven’t visited the Portland area yet, or haven’t been there in a while, it’s time to put it on your destination list. History buffs, foodies, active adventure seekers – Portland & the surrounding islands have something for everyone. Perfect for a long weekend destination, or an extended vacation getaway, and easy to access whether traveling by planes, trains, or automobiles. We’ve put together the ultimate Portland, Maine Itinerary for your next visit to this spectacular city.

Day 1 – Old Port

Start your Portland, Maine Itinerary by exploring the Old Port area of Portland with its historic district and cobblestone streets. A great place to start exploring is a walk along Commercial Street where you can take in the scenes of the working waterfront, which is integrated nicely with restaurants & boutiques.

Pick Up Some Historical Treats

Did you know, Portland has history that includes molasses? In the 18th Century, when they sent the lumber ships to the West Indies, the ships couldn’t sail the return trip empty, so they would send them back with molasses, which would then be used to make rum.

While on the waterfront, don’t miss the opportunity to pop into the Standard Baking Company (across from Casco Bay Lines Ferry Terminal) and pick up THE best molasses cookies, along with other handcrafted baked goods, many of which are made with 100% Maine grown and milled whole grains.

Do Some Unique Local Shopping

We’re a fan of Seabags , nautically inspired totes & bags, made out of recycled sails, and they are made right here in Portland!  When we popped into their store/shop (25 Custom House Wharf), we learned that in addition to all of the fun bags they have available in the store, you can also have one custom made. Other local unique boutiques we discovered included: Blanche & Mimi for interior, bath & antiques – Peyote Moon for unique fashion forward designs | Simon Pierce for handmade glassware & pottery.

Stop For Lunch

With its harbor views and unique character (a former car ferry converted into a restaurant), DiMillo’s On The Water is the perfect spot to observe the working waterfront. Local’s might call it a bit touristy, but for the atmosphere and the food, this restaurant is a must for drinks or dinner.   Tip: Arrive early and request a table on one of the outside decks.

Take A Stroll Through History

Next up on our Portland, Maine Itinerary: Make your way up Moulton Street to Exchange Street, where you will walk among historic buildings and find coffee shops, trendsetting boutiques, as well as several locally owned business selling items made in Maine. Wrap up your initial “get your bearings” walking tour by exploring Fore Street, where you will find more shops and restaurants, along with artisanal boutiques.

Check Into Portland Harbor Hotel

Given its prime location in Portland’s Old Port, the Portland Harbor Hotel is an excellent home base from which to explore the city. The Harbor hotel feels like a dreamy night at sea – with its nautical theme, the rooms have the feeling of a large, luxurious stateroom on a ship.  

Some nice complimentary perks that come with your hotel room:

• Each floor has a cozy sitting area with a Starbucks touchscreen machine, tea & sparkling water
• Complimentary bikes
• Concierge on site for suggestions
• Personal car service to all downtown restaurants & attractions (available on a first come first served basis)
• Outdoor dining & outdoor fire pit in a lush garden patio
• Drop your bags off if you arrive early before you begin the day of exploring

After a busy day of exploring, take a break before dinner and relax in the courtyard patio of the Harbor Hotel. It’s a hidden garden in the middle of the city, including a fire pit and cocktail bar.

With an elegant yet relaxed atmosphere, BlueFin North Atlantic Seafood restaurant offers an exceptional land and sea menu, and they are conveniently located right in the hotel.  Executive Chef Gil has an incredible passion for creating new and unexpected meals with fresh, locally-caught seafood and seasonal ingredients, and his passion comes through with the menu. A trip to this restaurant is a must-add to any foodie’s Portland, Maine Itinerary!

We were truly surprised and delighted with everything including appetizers: Lobster Scargot – Chef Gil’s signature dish – Lobster chunks in garlic butter with herb crumbled topping ($21), Pork Belly Lollipops ($14), Calamari “Fries” ($14), Seared Scallops with parmesan risotto with wild mushroom cab demi, crispy shallots & beet honey ($35), and Salmon with lemon beurre blanc, asparagus, leek nest, and carrot foam ($34)

Day 2 – Five Lighthouse Bike Tour

Jumpstart your day with a complimentary Starbucks coffee from the lounge area on your floor of the hotel, or head over to Bard coffee a fun unique cafe (185 Middle Street).

Grab A Bite

In my opinion, the next stop on our Portland, Maine Itinerary may just be the most important (or is that just my sweet tooth talking?) Since the day includes a bike tour, it’s a perfect day to stop in at Portland’s legendary The Holy Donut , and try one of their hand-made donuts that surprisingly include Maine potatoes in their recipe. Potatoes? Yes, we were skeptical at first, but we were quickly convinced after tasting their delicious donuts.  Their creative flavors rotate daily, but we highly recommend the dark chocolate sea salt, and the Maine blueberry. Enjoy having your coffee & doughnut outdoors? Make your way one block over to Tommy’s Park and check out local artist Will Sears’ colorful, abstract, mural while you morning treats.

Stroll over to the Ocean Gateway Visitor’s Center where you will meet your guide for the Summer Feet – 5 Lighthouse Bike Tour . Tip: reservations are required and book early during peak summer because the tours fill up.

Discover Greater Portland

During the bike tour (about 12 miles) you will explore the Maine coast, have time to take pictures at the 5 lighthouses ( Bug Lighthouse, Spring Point Ledge Lighthouse, Rams Island Ledge Lighthouse, Portland Head Lighthouse, and 2 Lights State Park ) plus learn local Portland and Maine history along the way.  While cycling from lighthouse to lighthouse we enjoyed hearing the history of Portland & its neighborhoods, and a variety of interesting facts. Plus, our guide shared the details on South Portland’s contribution to World War II (they built Liberty ships here using new technology for the time – ships were welded rather than riveted together), and the Gus Wilson collectible decoys , which he carved using pieces of driftwood while stranded in the Spring Point Lighthouse for a month! Tip: Bring water, camera & a jacket. The bikes have a rear rack bike bag to help you carry personal items.

Eat A Lobster Roll

Enjoy lunch (included in the tour) in the beautiful Fort Williams Park during a stop at Portland Head Lighthouse .  Prior to arriving at the lighthouse, your guide will take your order for your selection of the lobster rolls and then meet you at the picnic area once you arrive at Head Lighthouse.  The lobster rolls were d-e-l-c-i-o-u-s and included these options:

• Classic – with butter (Connecticut) or mayo (Maine)
• Picnic – with coleslaw

Alternate Shorter Bike Option

If you don’t have time for the 5 Lighthouse Tour, check out a complimentary bike from the Portland Harbor Hotel , or rent a bike from Summer Feet Cycling (near the Ocean Gateway Visitor’s center) and cycle along the Eastern Promenade Bike trail, which begins near the Visitor’s Center.  The Eastern Promenade trail is also a great option for walking along the scenic shore.

Paddle Up For A Different Point Of View

Yet another option is to see the lighthouses and other historical sites while kayaking in Casco Bay with Portland Paddle on their full-day Lighthouse & Fort Tour.

Hop On The Ferry

After wrapping up your day in Portland, hop aboard the 4:15 ferry with Casco Bay Lines and soak in the scenic coastal views during your 30-minute ferry ride. You should have no trouble finishing the bike tour, picking up your luggage, and making the ferry.

Step back in time with a relaxing stay on the scenic, car-free, Great Diamond Island, which is accessible by ferry, water taxi, or private boat. Note: there are two ferry stops on the island, so make sure to purchase your ticket to the Diamond Cove dock, and that you get off the ferry at the correct stop. Tip: Arrive early for the ferry in Summer season. All ferry tickets are roundtrip, and fares are collected in Portland when you purchase your ticket.

Take In The Ferry Views

While cruising on the ferry keep an eye out for the “green roof,” historic Fort Georges, built during the mid-1800s on Hog Island Ledge, in Casco Bay at the entrance to the harbor. Due to advancing technology at the time (in ships and long-range guns), the fort was obsolete before it was completed, and therefore never used. The fort is currently a park, and only accessible by boat.

Upon arrival at the Diamond Cove dock, a staff member of the Inn will meet your ferry and shuttle you and your luggage to the hotel via golf carts.

Check Into Inn At Diamond Cove

Built in the 1890s and a member of Historic Hotels of America, the Inn was originally the barracks of Fort McKinley whose mission was to help protect Portland’s Harbor and Casco Bay. With its immaculate renovations and design, it’s hard to imagine that this was formerly a simple army Barracks.

The spacious 44 rooms exude luxury, and the cozy decks with lounge chairs give you a feeling of being at that ultimate adult summer camp. Amenities include a heated pool and hot tub, yoga studio (also offered outside on the parade ground Sunday at 9 am), unique vintage indoor basketball court, croquet, and duckpin bowling. Ultimately, most guests come to the Inn to relax and unplug.  While there is wi-fi at the Inn, it’s not super strong, so it’s the perfect time to unplug and be present. Tip: During check-in, ask the concierge to make you a reservation at the Diamond’s Edge restaurant for day 3 of your trip.

If your group includes family or friends, the rooms and suites can easily share outdoor space with the moveable deck dividers.  Also, if your family requires accessibility or mobility needs, the hotel is very accessible, the staff can shuttle you around the island on the golf cart as needed, they are adding an accessible chair to the pool (available late Summer 2019), and they are working to make the local decommissioned military bunkers, which are available to tour, fully accessible in the near future.

Enjoy some relaxing time before dinner on your deck, at the fire pit, or in the hot tub. Cocktails are conveniently available at either the lobby bar or the cabana bar.

Vacation is the perfect time to operate with a flexible schedule, so take your time with a cocktail hour and head into the Café for dinner when you’re ready.  The cozy, casual, patio setting is the perfect ambiance for a relaxing evening meal. Make sure to try the Seafood Chowder ($9), Shrimp Scampi ($29) and Honey Mustard Salmon ($30).

Day 3 – Exploring Great Diamond Island

Start your day.

Start day three of your Portland, Maine Itinerary by enjoying a peaceful breakfast on the patio, coffee on your deck or by the fire pit, then pick up a map from the concierge and head out to tour the island by foot or use the complimentary bikes available at the resort.  Break it up by beach section, or map out a route and do the grand tour. Either way, you’re sure to discover hidden treasures like pottery artifacts from the old days on Pleasant Cove Beach, or the former military bunkers. Just make sure to ask the concierge which ones are safe to explore!

Take A Tour

If you would like an overview guided tour of the area surrounding the Inn, there are two tour options on our Portland, Maine Itinerary. The short tour option (20 minutes), is presented by the hotel staff on a golf cart, and will give you more of an overview of the Inn’s history, as well as a tour to the beach locations. The more detailed and lengthy tour (1.5 hours), is guided by volunteers from the historical society, and gives you deep contextual history about each individual building on this side of the island. You can reserve both through Concierge at the Inn. Fun fact: keep your eyes open as you are touring, some of the private residences on the island have incorporated the bunkers into their homes with unique designs.

Dine Like A (Casual) Royal

For lunch head over the marina area where you will find the fun and funky Crown Jewel . Their food is small plates, so order a few to share.  Make sure to try the Fun Fact: Due to water restrictions on the island, Crown Jewel is not allowed to wash dishes, however they have been incredibly eco-conscious in dealing with this restriction and 95% of the utensils and plates used at the restaurant are compostable.

Mosey Around

Spend the rest of the afternoon continuing your island self-guided tour, playing a game of tennis or croquet, or grab a book and head to the beach or pool for more relaxation.  We opted to continue our island tour and explored the areas adjacent to the marina including Diamond cove beach, before making our way back to the Inn for an afternoon cocktail.

Treat Yourself To A Waterfront Dinner

For your final night on our Portland, Maine Itinerary, enjoy dining at Diamond’s Edge Restaurant (the former quartermaster’s storehouse) where the food is superb, and the waterfront setting overlooking Diamond Cove is spectacular. With so many menu options including locally sourced seafood, as well as choices for landlubbers, your decision on what to select may be a bit difficult. Favorites include: the Maine Crab Cake ($16), Bangs Island Mussels ($14), Ginger Glazed Tuna ($34) and Pan-seared Scallops ($36) Tips: Outdoor dining options include deck or lawn, weather permitting. Also, arrive early for pictures on the pier. The setting sun was beautiful and we found ourselves wishing we had more time for photos.

Tip: For the ultimate relaxing experience, book your trip altogether with the Portland Land & Sea package with either the Portland Harbor Hotel or the Inn at Diamond Cove . This package not only combines your hotel reservations, includes most of your meals and ferry ride, it also allows you to park your car at the Portland Harbor Hotel (valet parking only – $22/night) and request that the hotel transport your luggage to Inn at Diamond Cove upon checkout.  This leaves you free to explore Portland on day 2 before showing up at for your ferry departure.

Staying longer and want to explore more of Portland? Check out our list of the 15 best things to do in the city!

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Monday 24th of June 2019

I love your description of Maine. I feel I was there. Thank you for sharing such wonderful experience

Tuesday 25th of June 2019

Glad you enjoyed it Frankie! It's truly a wonderful destination, full of hidden charm and vibrant coastal activities!

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• Sep 1, 2022

Portland, Maine: Perfect 3-Day travel itinerary for a summer long weekend

If you're looking for an easy long weekend, 3-days in Portland, Maine is the perfect summer getaway. Did you know Portland has been named in the past as the best food destination in the USA? And is home to some of the best-voted lobster roll restaurants in the country too? In this guide, you can expect to find the best places to eat and explore all planned out in an easy-to-follow 3-day travel itinerary including lighthouse spotting, island hopping and plenty of good food.

Where to stay in Portland, Maine:

We'd recommend 1 of two options for accommodation:

Note - This post contains some affiliate links if you use them we will receive a small commission at no extra cost to you.

If you don't have a car: Old Port

Old Port is full of the cutest cobblestone lanes, red brick buildings housing bars, restaurants, cafes and stores, plus is located right on the waterfront overlooking Casco Bay, with direct access to the piers where many of the ferries for island day trips and tours depart. Everywhere within Old Port is centrally located and within walking distance making it the perfect spot if you don't want to rent a car as part of your trip.

Hotel Options in Old Port, Portland, Maine:

If you rent a car: South Portland by Willard Beach:

This is a great option for a more relaxed neighbourhood feel. The suburb is filled with beautiful beach houses and is within walking distance of the beach and cafes. There aren't many hotels located here, so the best option would be an Airbnb if you want to stay in this area.

Top things to see, do, eat and drink in Portland, Maine: A 4-Day itinerary

Day 1: South Portland, Willard Beach & Old Port

Morning Day 1:

Breakfast at Scratch Bakery , South Portland - Don't miss their bagels, arrive early as they sell out fast. They also do great coffee and pastries.

Visit Fort Prebble & Spring Point Lighthouse , walking distance from Scratch. Take the 20-minute coastal walk along Willard beach through to the lighthouse and back

End the morning with a swim at Willard Beach , also don't miss visiting Fishermans Point for the best views overlooking the beach

Afternoon Day 1:

Have lunch at Duck Fat Frites in Old Port and don't miss their Poulet, which is fries coasted in duck fat with gravy and shredded duck. Their original milkshakes are also great.

After wander around Old Port through the cobblestone streets. Be sure to stroll down Wharf Street and stop in the shops around Exchange and Market Streets. Commercial Street is great for restaurants and bars.

Evening Day 1:

Grab some takeaway food, we recommend the clam chowder from Gilberts and watch the sunset at Bug Light park and lighthouse in South Portland (10-minute drive from Old Port)

Day 2: Visit Boothbay Harbour & Wiscasset

Morning Day 2:

Take a 1.5-hour scenic drive to Booth Bay Harbour. Have a quick breakfast along the waterfront at Red's Coffee House (We recommend the blueberry scrolls).

Book a tour with Cap n' Fish cruises , they have 1-hour harbour sightseeing cruises, as well as longer 2-3 hour cruises including whale and puffin watching. We booked the Puffin watching, which we would recommend. If you do this one bring binoculars or a camera with a good zoom lens.

Afternoon Day 2:

Driving back in the direction of Portland, stop to try Red's Eats Lobster Rolls or Sprague Lobster in Wiscasset.

Red's Eats has been voted as the best Lobster rolls in Maine and has been featured on numerous travel shows like Somebody Feed Phil. You can expect to wait up to 2 hours to order here with long queues forming daily. If you don't want to wait, located right across the road is Sprague Lobster which we opted for and was the best lobster rolls we had of the trip. Be sure to order it with the melted butter.

After lunch take a de-tour drive through Bailey Island , stopping to enjoy the coastal walks and views.

Evening Day 2:

Have dinner at The Honey Paw (Asian Fusion) or Via Vecchia (Italian Food) in Old Port depending on what you are feeling like. If you can we recommend making a reservation in advance.

The Honey Paw:

Via Vecchia:

Day 3: Portland Head Lighthouse, Fort William Park, and Peaks Island

Morning Day 3:

Have breakfast in Old Port, picking up pastries from The Standard Baking Co (expect a queue if visiting over the weekend so arrive early) or the Holy Donut (Amazing potato-based donuts, their salted chocolate is their best seller).

Drive 20 minute south to explore Fort William Park and Port Headland Lighthouse. Be sure to take some of the coastal walking trails while there.

Have lobster rolls for lunch in Fort William Park from the Bite Into Maine food truck (Also featured as one of the best eats in Portland on Somebody Feed Phil).

Afternoon Day 3:

Take the ferry from Casco bay to Peaks Island, It's just a 15 minute ride across, with the ferry running around every hour

Getting around Peaks Island: The island is 4 miles around, and will take about 2 hours to explore . You can rent a bike from Brad's located just a 5 minute walk from the ferry terminal for $20 for 2hrs. Alternatively you can also rent golf buggies on arrival too for around $90 an hour, be sure to pre book these before your visit as they sell out (Try Peaks Island Rental).

Places to see: don't miss the Battery Steele and Civil War Museum.

Have dinner at the High Roller Lobster Co , for more amazing lobster rolls, the fresh oysters are great there too.

We hope you enjoyed our long weekend travel guide to Portland, Maine. To see more of our other USA destination guides click here .

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Best Things to See + Do in Greater Portland, Maine

Looking for things to do in Portland, Maine and beyond? Our diverse coastal area is centrally located, where nearby regions welcome visitors with their own distinctive Maine experiences. It’s all at your fingertips. Sea you there…

Must See + Do

Unlock what makes this coastal community a must-do destination. From history and landmarks to craft brews and bites, there are so many reasons spend your vacation in Greater Portland, Maine.

Explore the Maine Coast

The perfect way to experience the coastal and inland areas of Greater Portland Maine.

Maine offers plenty of outdoor adventure, parks, and hands-on fun.

Constant attention to landmark preservation has made Maine a historical destination.

Whitewater rafting, camping, fishing and hunting trips – on the water or on land.

Just one visit and it’s easy to see why so many people add shopping to their list of reasons to come to Greater Portland Maine.

Featured Events

There’s always something to do in Greater Portland, Maine.

From daily tours to cruises, art exhibitions, music, and live performances.

Browse our Events Calendar and save your favorites.

Always cross-check event time/date with organizer’s website before booking. 

Prepare for the solar eclipse on Apr 8th.

Welcome the warm weather and enjoy some good food with the award-winning The Lobster Shack!

Come to Sunday River and enjoy the best views of the 2024 Solar Eclipse!

Come view the Solar Eclipse with us at Pineland Farms!

Kick off summer with a week of wine in Portland!

Must-see + Do, Day Trips, In + Outdoor Fun – Find it all in Maine

As visitors survey the scenic vistas of this historic city on Casco Bay , gaze at boats that come and go from the waterfront, and watch the activity along the downtown’s cobblestone streets, finding things to do may be the furthest thing from their minds. For those preferring to focus on filling their days with fun activities and enduring memories, Greater Portland delivers. Visitors will find kid-friendly amusements, must-see attractions, day-trips, and nightlife for every taste and style and every family member.

Greater Portland means great getaway, vacation, and long-term stay opportunities each season—from high-octane to low-key, indoor to outdoor, land or sea. This metropolitan city with small town charm is a cultural mecca and wildlife wonderland. It is the home of microbrews and sea cruises , of a world-class food and art + culture scene. Where shopping , sailing, or hitting the beach is at its best.

VISITOR INFORMATION

When you’re in town, stop by our Visitor Information Center to pick-up brochures, Visitor’s Guides, maps of the region, and plenty of pro-tips to help make the most of your stay in Greater Portland.

OCEAN GATEWAY – SEASONAL HOURS: Mon to Sat – 10am to 3pm Sun – closed

Plan Your Trip

Plan your trip to Greater Portland Maine. Explore Maine’s local brew scene, a variety of walking tours, history and landmarks, and much more. Love the water… take a sailing excursion or boat tour. Love to shop.. fine unique local shops. Store things of interest like upcoming events and your favorite activities. Then send your trip plan to your family and friends.

Online Shopping

So many people add shopping to their list of reasons to visit Greater Portland—from handcrafts to haute-couture. By shopping online at our local boutiques and shops, you can bring a piece of Maine straight to your front door. It might just be enough to hold you over until your next trip to Greater Portland!

Packages + Deals

Browse through the special packages and deals offered by participating businesses. Find special deals on tours and attractions to maximize your visit. Enhance your shopping experience and find that perfect gift or souvenir. Don’t forget to enjoy the food scene. Find discounts and happy hour specials.

On The Blog

Join lifelong Mainers, Amy + Dan, as they make their way down the coast for seven days of fun in the sun—exploring a bit of everything Maine has to offer.

Across Greater Portland we are bringing the fun with annual fairs, festivals, and exciting events all year long and for all ages.

If you’re considering the Northeast for a meeting, event, or conference—it is time to start thinking about hosting in the Greater Portland region!

We know how much goes into capturing those perfect moments that live on long after you leave, here are some inspiring photo hot spots.

How would YOU live like a local? Peek our Maine itineraries for a ideas on how you could spend a fun-filled day like no other in Greater Portland.

There’s no shortage of beautiful, stunning places to snap, but these are the ones that come up as some of the most romantic, time and time again.

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The Perfect Three-Day Weekend in Portland, Maine

Travel + Leisure is exploring America one three-day weekend at a time. Here's what to do on a short trip to the picturesque coastal New England town.

Portland, Maine: an often-buzzed-about, lobster-lover’s paradise where waterfront industry, a dynamic local art scene, and the smell of the sea make for one of the East Coast’s finest north Atlantic escapes. The city has gained much recognition in recent years—and for good reason. Portland has come into its own exciting cosmopolitan moment, developing an impressive collection of restaurants, bars, and breweries while remaining a historic icon of the Northeast. If you’re looking to scout out some of the best seafood and local breweries while catching a salty breeze, head north for a classic New England three-day weekend—itinerary on us.

If you’re arriving at Portland’s local airport, PWM, it’s only a five-mile drive to where you’ll be staying at the Press Hotel, which is located in the historic Old Port district. Drop your things and take a moment to appreciate the hotel’s history—it used to house the Portland Press Herald headquarters, and gives subtle nods to the newspaper industry through rooms inspired by 1920s writing offices and clever in-house venues like the Inkwell bar.

After settling in, make a beeline to Commercial Street. Sit on the waterfront for an early lunch at one of the city’s best chowder spots, Gilbert’s Chowder House —a local favorite where the vibe is casual and the seafood chowders are award-winning.

Following lunch, head to the Portland Museum of Art at Congress Square, which is home to an impressive collection of European, American, and contemporary art, as well as an active rotation of exhibitions featuring local Maine artists and legendary works from around the world. When you’ve gotten your fill of PMOA, take some time to wander in and out of the many art galleries, thrift shops, and boutiques that line the streets downtown. Be sure to stop in Longfellow Books and the Art Mart .

When you’ve gotten your fill of exploring, and if you have access to a car, head about eight miles south of Portland to Cape Elizabeth’s Crescent Beach and spend the rest of the day soaking up the sun and salt water. If you’re on foot, walk over to East End Beach on Casco Bay, about a 20-minute walk from the heart of downtown Portland.

Go back to your hotel for a glass or two of rosé at Inkwell, followed by a relaxing dinner at the Press’s UNION Restaurant , helmed by Maine native chef Josh Berry. Feast on dishes like pan-roasted Maine salmon with summer corn fondue or seared local cod with Maine lobster, clams, and coconut nage.

Now that you’ve settled into the city, it’s time to explore what Portland has become very well known for: a thriving local beer scene. After a laid-back morning at the Press, walk about 10 minutes down to Commercial Street to Standard Baking Co . and enjoy organic local pastries and a coffee. Take an hour to stroll the shops of Commercial Street, which was named one of the best streets in the U.S. by the American Planning Association in 2008. Some can't-miss spots: Portland Dry Goods , Browne Trading Market , Asia West , and Edgecomb Potters .

Now, time for the brews. If you’re traveling by car, it’s no trouble to drive around the greater Portland area to tour various breweries (like the esteemed Allagash Brewery and Bissell Brothers Brewing Company ), but the easiest option is to hop aboard the Maine Brew Bus , which leaves for tours from the Portland Beer Hub on Fore Street. The bus takes beer lovers from venue to venue on an all-inclusive, behind-the-scenes tour of Portland’s craft breweries. At $55 per person, the tour bus varies which breweries it makes stops at depending on the day of the week and the theme of the tour (tours run midday on weekends and weekdays, lasting for several hours). Breweries include (but are not limited to): Maine Mead Works, Oxbow Blending & Bottling, Geary’s Brewing Co., Rising Tide Brewing Co., Foulmouthed Brewing, Lone Pine Brewing Co., Maine Beer Company, and more.

If you can, do your best to track down the High Roller Lobster truck, which frequents a few of the local breweries (like Bissell Brothers and Oxbow Blending), and sells rolls bursting with fresh Maine lobster on a local brioche bun—add-ons like avocado and bacon are a must-have.

When you return to Commercial Street in the afternoon, you may be ready for a nap back at the hotel. But if you’re looking to walk off the brews, take a stroll on the Eastern Promenade Trail , which snakes along the Casco Bay waterfront and connects to Back Cove Trail.

Make your way back into town for a farm-to-table dinner at Fore Street (which is part of the same local restaurant family as Standard Baking Co.), just a block away from the waterfront. Enjoy a menu that rotates daily, featuring fresh and foraged local fare. After dinner, grab a cone on Exchange Street at Mount Desert Island Ice Cream .

Take your time and enjoy your last morning waking up at the Press—maybe opt for the Baseline massage at Akari Spa . Walk five minutes to Exchange Street to start the day at Blake Orchard Juicery with a freshly pressed juice or smoothie.

Today is all about taking advantage of Portland’s proximity to the ocean. Make sure you’ve got some layers with you (being on the water can get chilly!), walk to Commercial Street, and seek out Odyssey Whale Watch . Spend the day out on the boat trying to spot humpback whales up to 20 miles off the coast of Portland.

When you return to Commercial Street— if you haven’t gotten your fill of seafood yet—grab a late lunch at Portland Lobster Company . You can sit on the outdoor deck and feast on lobster rolls and fried clam baskets, or order from the to-go menu and take your food down to the water at East End Beach for a picnic.

Take the rest of the day to wander around Portland, in and out of shops, galleries, and cafés. Start your evening at a local gem, Eventide , where the fresh oysters on ice greet you the moment you walk in the door. You’ll come for the bivalves and cocktails, and stay for one of Portland’s finest seafood menus—think battered Maine hake, lobster stew, and a quintessential New England clambake.

After getting your fill of seafood, head to Market Street for post-dinner drinks at Portland Hunt & Alpine Club , a modern Scandinavian bar that features a cocktail menu divided into four parts: Refreshing, Adventurous, Classics, and Wild Card. Take your pick and enjoy your last night in Portland over a handcrafted drink. From the bar, it’s just a two-block walk back to the hotel.

Check out these other long-weekend getaway ideas to some of America's best vacation destinations.

Ellie Storck is the Digital Editorial Assistant at Travel + Leisure. Follow her on Instagram at @ellienan.

How to Do Coastal Maine in 7 Days: Two Day Portland Itinerary

A trip to Maine is incomplete without a short visit to its most populous city, Portland. I recently put together a road trip, “Coastal Maine in 7 Days”, that I used to get out and see small-town Maine and the state’s beautiful Atlantic coastline. While Portland is not small-town Maine, it is an important part of the state and a city you shouldn’t miss if you are in the area. A two day Portland itinerary is a good amount of time to get a feel of what the city has to offer.

This is the third and final post in the series where I will take you along for the trip. I’ll show you the itinerary I used so that you can replicate and experience everything that Maine has to offer. The first post covered arrival in Maine and exploring the small coastal town of Camden. The second post covered Bar Harbor and Acadia National Park. If you haven’t read either of those two posts, I encourage you to do so.

This post starts with leaving Bar Harbor and seeing one last major sight in Acadia National Park. From there, the road trip winds its way back south towards Portland with several stops along the way. The limited time in Portland is spent enjoying some of the things that have made the city famous: lobsters, food, and beverage experiences.

Post Contents

Day 6 – Portland

As the end of the vacation week approaches, it is time to move on to the final city on the itinerary, Portland. As with the journey North, the journey back will stop at several places along the way. Prior to leaving Bar Harbor, there is one final stop in Acadia National Park.

Cadillac Mountain

• Destination: Cadillac Mountain
• Duration: 30 minutes driving
• Suggested Timeline: 8:00 AM – 8:30 AM

The highest and most well-known peak in Acadia National Park is Cadillac Mountain. This mountain rises 1,520 feet above sea level and is located very close to the coast providing great views of the surrounding area. It would be unfortunate to come to Acadia and miss its highest peak. While you could definitely hike to the top, there is also a road that goes to the summit. Given the short time in Acadia National Park, I recommend driving to the top of this one to squeeze in as much as possible.

The drive up to Cadillac Mountain is a very popular activity. Therefore, the National Park Service has begun to require vehicle reservations during the high season (May 26 th – October 19 th ). Vehicle reservations cost $6, and you must purchase them ahead of time on recreation.gov . As these tickets are popular, it can be somewhat hard to get the times that you want. 30% of tickets are made available 90 days ahead of each date. The US Park Service releases the remaining tickets at 10 AM ET two days ahead of each date so plan accordingly. You must have a park entry ticket in addition to the vehicle reservation to get to Cadillac Mountain.

Two types of tickets are offered. The first ticket is a sunrise ticket. Sunrise tickets are limited. These tickets allow the holder to go up to the top of Cadillac Mountain to watch the sunrise. Cadillac Mountain is the first spot in the US to experience the new light of each day. Add that to the scenery, and you have an amazing end to your time in Acadia. Sunrise is often between 4 AM & 5 AM during the summer so this does mean a really early morning if you choose this route.

Cadillac Mountain – Alternate Times

If you aren’t an early riser, daytime tickets are also sold. These tickets provide a 30-minute entry window to the mountain. While you won’t get the amazing sunrise and the early morning views of Acadia, the Atlantic, and Bar Harbor, the daytime views are almost as good. I obtained this type of ticket on my recent trip due to the sunrise tickets being sold out.

Breakfast and Checkout

Take your time in the morning having breakfast and checking out. If you did not want to do sunrise at Cadillac Mountain or if you were unable to secure a ticket for that time, do Cadillac Mountain right after checking out and before getting on to the road to Portland.

Drive to Portland

Today will mostly be spent driving back towards Portland with a few stops along the way. As with the journey north, the drive will mostly take place along US Highway 1 (the Atlantic Highway). Many of the sights and towns along the way should be familiar from the drive up. If there was anything that caught your eye on the drive north, I encourage you to stop in on the way back to Portland. Included below are a few of the recommended places to stop along the journey South.

Owls Head Lighthouse

Owls Head Lighthouse is a prototypical white lighthouse. Originally constructed in 1825, Owls Head Lighthouse stands roughly 100 feet above the water. The lighthouse is located a short walk down a gravel road from the designated parking area. While some of the best views of this lighthouse are from the water, approaching from land will allow you to go right up to the base of the lighthouse. The visit to the lighthouse can be a quick stop to stretch the legs and get a good view. Alternately, take a little more time to get a lighthouse tour. With a tour, you are able to go up and see the inner workings of the lighthouse and the panoramic views from the top.

As you get back on the road, start looking for places to eat lunch. If you are ready to eat immediately upon leaving, Rockland, Maine is the closest town that will have several options. If you aren’t yet ready to eat, the drive to the next stop is just over an hour. The route continues along US Highway 1 and through several towns along its path. There are many options as you drive to pick up food later as well.

Androscoggin Swinging Bridge

The Androscoggin Swinging Bridge is a pedestrian-only wire rope suspension bridge. The bridge spans the Androscoggin River and connects the two small Maine towns of Brunswick and Topsham. While there isn’t anything that you have to see in Brunswick or Topsham, the bridge is a unique enough construction that it is worth a quick stop. The views from the center of the bridge overlooking the Androscoggin River are also nice and peaceful during the summer months.

The swinging bridge was constructed in 1892 and has gone through several renovations over the years to keep it usable. The US National Register of Historic Places recognized its historic significance by adding it to its register in 2004. While it is completely safe to walk across, the swinging bridge does live up to its name. Expect to feel the bridge move up and down (especially in the center) when there is sufficient traffic on the bridge. If this frightens you, stay to the ends of the bridge. The movement of the bridge surface will be the smallest at the edges of the bridge.

At each end of the bridge, a small park and areas for parking have been constructed. This makes visiting the bridge very easy and a pleasant walk to break up the drive south. While the parking areas at each end of the bridge are small (4 – 5 spots), the surrounding residential areas allow parking on the side of the street. Therefore, parking in close vicinity should never be a concern.

L.L. Bean Headquarters/Flagship Stores

This stop isn’t an absolute must if you don’t know the L.L. Bean brand. However, if you know and grew up with the brand, I recommend making a stop. L.L. Bean, which is famous for its outdoor gear and apparel, is headquartered in Freeport, Maine. Freeport is located along your drive back about 30 minutes north of Portland. The L.L. Bean headquarters and flagship store is actually a campus of several buildings with different specializations. There is an entire building dedicated to clothing, bags, shoes, and camping gear. Another building is dedicated to fishing and hunting gear. Another building houses homewares/decorating items, and a final building is completely dedicated to bedding.

The superstores dedicated to mostly outdoor gear have the feel of a refined Cabella’s or Bass Pro Shop. Each individual store isn’t as big as one of those megastores, but it still has large displays and a whole lot of inventory. These stores make for some great browsing if you are interested in outdoor wear, hunting, fishing, or camping. It’s also impressive to learn the history of the brand and see how it started as a small Maine store and grew to an internationally recognized brand in the outdoor world.

The L.L. Bean headquarters takes up a two-block area in what has become known as the Freeport outlets. If you find that L.L. Bean isn’t your style or if you have additional time to shop, there are many different outlet store options in the area that may be of interest. Options include:

• The North Face
• Brooks Brothers
• Vineyard Vines
• Under Armour
• Dooney & Bourke
• Polo Ralph Lauren
• Levi’s

The L.L. Bean headquarters and flagship store was the last stop on the drive back into Portland, Maine. Portland is a short 23-minute drive south via Interstate 295. You should head to your hotel to check in, drop bags, and park the car.

After a day full of driving and stops along the way, you have finally arrived in Portland. The first stop should be to check into your accommodations and park your car. The best area to get accommodations in Portland is the Old Port area. This area is full of elevated-experience restaurants, cafes, bars, and shops. The Old Port neighborhood is also located next to the Portland harbor providing easy access to waterfront activities and exploration. The area retains portions of its history with the industrial and fishing-based docks and several cobblestone streets.

On the second to last night of the vacation, take some time to enjoy a nice dinner in the Old Port area. If you are traveling during the summer, consider doing some restaurant research ahead of time and make reservations to ensure you have a table. Summer is the high season for travel; therefore, lines at popular dinner locations may be long without reservations. As with many places in Maine, most restaurants start closing around 9 PM.

Day 7 – Portland

Portland Lobstering Excursion

Maine is known as the lobster capital of the United States. While I hope you have eaten lots of lobsters by this point in your trip, you should take the opportunity to actually go lobstering and catch some of your own. For this experience I recommend Lucky Catch lobstering.

Lucky Catch takes passengers on about a 90-minute lobstering expedition in Casco Bay (the bay right outside Portland). The boats have a maximum capacity of approximately 20 people per trip. While this is not a private expedition, with only 20 people everyone will have an opportunity to get up close and personal with the lobster traps. The two-person crew does an excellent job of educating everyone on how lobstering is done, the history of lobstering, and the rules and regulations on catching lobsters sustainably.

Everyone is given an apron and gloves and encouraged to get into the action. All groups are given an opportunity to pull lobster traps, clean and re-bait the traps, place bands on lobster claws, and much more. With any luck, your tour with come back with 6-8 keeper lobsters. You will likely catch more than that, but many will have to be thrown back because they are too little or too big.

An added bonus to the lobstering excursion is that you get some great views of the Portland surrounding area from the water. While this is by no means a historical or sightseeing tour, the staff does point out places of significance. You also get some great views and pictures of Fort Scammell, some islands in Casco Bay, and Portland Head Light from the water.

Walk Away with a Lobster

Finally, the excursion ends with the opportunity to take the lobsters you caught with you so that you can eat them. Lucky Catch sells the lobsters to any of the passengers at the “boat price” or a little less. While the lobsters aren’t free/included in your tour, if you are going to eat lobsters afterward this represents a good discount off the normal price of a lobster. Bring cash if you want to purchase a lobster as they are unable to take a card on the boat. Lucky Catch has also partnered with the Portland Lobster Company restaurant. This restaurant is located at the end of the pier where Lucky Catch docks their boats. Portland Lobster Company will cook the lobsters you bring from the excursion and provide sides for a very reasonable price.

Lobster Lunch – Portland Lobster Company

With a lobstering expedition checked off your list and a lobster from the expedition in hand, head to the Portland Lobster Company. This famous Portland restaurant is located right on the water and has tons of outdoor seating along the harbor (indoor seating is limited so be warned if the weather is not good). Take your lobster(s) to the restaurant; they will steam it and provide sides (butter, coleslaw, baked potato, etc…).

This is a great way to enjoy some of the freshest lobster that you will ever have. Even if you aren’t bringing your own lobster, the restaurant is still great. They have many different lobster and seafood dishes on their menu. In addition, the outdoor tables overlooking the harbor are a great way to enjoy a warm Portland day.

Old Port Exploration

The Old Port area of Portland is one of the most newly-developed and revitalized areas in downtown. For this reason, it is fun to explore the area on foot. You will find many interesting shops, cafes, and restaurants in the area. The streets to focus on are Commercial Street, Fore Street, and the small side streets that run between these two and out onto the docks.

Breweries and Distilleries

Portland is well known for craft breweries and distilleries that call the city home. If you are interested in trying some of the local creations, one or two of the following stops should be on your itinerary. While our itineraries often don’t provide options, there are three possibilities below depending on your preferences (beer, cider, mead, or spirits). While you could hop between all of these in an afternoon, most of these stops produce a wide variety of options. I encourage you to get a wider sampling at fewer places rather than moving between them rapidly. All of these options are located just north of the Old Port area.

Shipyard Brewing Company

For craft beer lovers, look no further than Shipyard Brewing Company. Shipyard is the closest location to the Old Port area being only about a 10-minute walk from the Portland Lobster Company. This brewery has a large rustic-style tasting room where you can sit to sample over 20 of their beers that are constantly on tap. In addition to beers, Shipyard also has a line of non-alcoholic Capt’n Eli’s Sodas. If you have someone in your group who isn’t a beer drinker, these craft and flavored sodas are a great way to have something for them.

Oxbow Blending & Bottling/Maine Mead Works

While these are technically two different businesses, they are located in buildings right next door to each other, and therefore it is easy to try either or both.

Oxbow Blending & Bottling

Oxbow Blending and Bottling is a part of Oxbow Brewery. This brewery is known for producing many different styles and varieties of farmhouse ales. While the brewery is located north of Portland in Newcastle, Maine, this location serves as an aging and blending warehouse for many of their unique beers that ferment for a longer than normal timeline. Many large oak barrels performing this task are clearly visible lining some sides of the tasting room.

If you enjoy being experimental with your beers, then Oxbow is the place for you. Their menu includes so many different and interesting combinations that you won’t find in many beers elsewhere. Some of these ingredients include pinot noir juice, lemongrass, Maine wildflower honey, and maple sap.

Oxbow Blending & Bottling Quick Info

• Website: https://oxbowbeer.com/location/portland/
• Hours of Operation : Sun – Wed 12 PM – 9PM; Thurs 12 PM – 11 PM; Fri & Sat 12 PM – 12 AM

Maine Mead Works

Mead is growing in popularity and making a comeback among many drinkers. If you like mead or have an interest in trying mead, Maine Mead Works is a great producer. The mead works have a very clean and airy space appropriate for the lighter, refreshing drink. Maine Mead Works generally has about a dozen meads available, so you can do a tasting (half-pours) of several to find the one you like most.

In addition to mead, they also sell local honey products and partner with Duckfat, a local eatery known for its snacks and small bites.

Maine Craft Distilling

The final option if you aren’t into beer or mead is Maine Craft Distilling. This craft distillery has its own variety of many of the staple spirits: whiskey, white rum, spiced rum, vodka, gin, and brandy. In addition to some of the traditional spirits, they make less standard liquors like blueberry liquor, aged gin, cinnamon vodka, and a chesuncook spirit (carrot, juniper, basil, mint, and coriander). Maine Craft Distilling also makes special cocktails with all the above at their bar on-site and has recommended food pairings.

In addition to the spirits, Maine Craft Distilling is known for its cocktails in a can. They make six different cocktails that are blended and canned. While the special cocktails at the bar are probably a better way to sample the local product, the canned cocktails are unique. I wouldn’t hold it against you if you were to have one as a taste test to see if you wanted to take a 4-pack home.

Portland is known as a gastronomic destination. While lobster is the local specialty, there is so much more food (both other seafood and non-seafood) that is well done in downtown Portland. Take a look around the Old Port area for an excellent restaurant for dinner.

Day 8 – Travel Home

Sadly, the final day of the vacation has arrived, and it is time to travel home. Spend some time this morning grabbing breakfast, packing, and heading back to the airport.

Don’t forget to refill the gas in your rental car. There aren’t any gas stations immediately at the entrance to the airport. Therefore, make sure you look up a gas station along the route before you depart to ensure one is on the way.

Bottom Line

This wraps up the two-day Portland itinerary and the final two days of the Coastal Maine in 7 Days road trip (if you are following that series). If you haven’t seen the other two parts of this itinerary ( Camden and Bar Harbor ), I encourage you to check out those two parts and consider seeing the beautiful nature in the northeast United States. If you have any questions on this part of the road trip or any of the road trip parts, leave a comment below.

Stay tuned as the Maine itinerary series is wrapped up with a couple more posts on when to travel and some tips & tricks to know before you go.

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Addison Osborn

Pingback: How to Do Coastal Maine in 7 Days: Bar Harbor and Acadia National Park

This was a wonderful itinerary. May I get a copy of it?

Mary, thanks for reaching out. The itinerary page for Maine is here: https://thevacationwingman.com/itinerarylibrary/north-american-itineraries/united-states-itineraries/coastal-maine-in-7-days-itinerary/

This will link you to all the sections of the itinerary along with descriptions of activities and helpful tips.

On that page, you should see several items marked premium content. A Microsoft Word download of the itinerary as well as cost analysis and helpful logistics information is provided to our site members as premium content. As the first person to comment on this post, use MARY365 when signing up for a free year of access to our premium content.

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New England Wanderlust

Maine  ·  August 3, 2022

15 Awesome Day Trips From Portland, Maine (2024)

Portland is a wonderful city in its own right, but it’s also centrally-located to some other amazing places. If you live in Portland or are new to the city, and are looking to get out and explore more of the region, or if you’re planning a longer stay and are wondering what your options are for day trips from Portland, Maine, this post is all about the absolute best options to give you plenty of ideas.

Even with just a day trip from Portland, you’ll be able to see some incredible coastal landscapes and lighthouses, go on some awesome tours, eat some delicious food and feel like you had a true vacation while only being gone a day. Having travelled all over Maine for over 10 years , I’ve seen so much of what the Pine Tree State has to offer, and I’ve scouted out the places that are worth your time!

With that, let’s jump into my favorite day trips from Portland, Maine!

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Best Day Trips From Portland, Maine (2022)

Below is a list of my favorite day trips from Portland, Maine, and the destinations are organized by shortest to furthest distance from Portland. Most day trips from Portland, Maine on this list are less than 2 hours away, with the longest being 2 hours and 30 minutes away. And be sure to keep reading below for bonus seasonal suggestions, as to find out if a day trip from Portland to Acadia is worth it!

1. Kennebunkport, ME

Distance From Portland: 40 minutes

The easiest, and also one of the best day trips from Portland, Maine is Kennebunkport. I love Kennebunkport because there’s so much to do, but it’s also a small town that’s easily manageable for a day trip. It’s packed with tons of charm, has some great beaches, awesome shops and restaurants and feels like a true escape from city life in Portland.

Some of the best things to do on a Kennebunkport day trip from Portland:

• Explore the shops & restaurants along Dock Square.
• Go for a swim or walk on the shoreline of Gooch’s, Mothers or Colony Beach.
• Take a drive on Ocean Avenue.
• Get a lobster roll at The Clam Shack.
• Walk along the coast of Cape Arundel on the Parson’s Way Trail.

A really great tour option in Kennebunkport if you’re a foodie is a culinary walking tour . Each tour is different based on the season, but it lasts for 2.5 hours, and you’ll get the inside scoop from a local on all the best foods to eat in town. They’ll take you to some off-the-beaten path places, and you’ll meet with food artisans to sample locally-caught lobster, chowder, Maine whoopie pies, the absolute best ice cream in town, and so much more. For everything you get with this tour, I think the cost is very reasonable!

Click here to book your Culinary Walking Tour in Kennebunkport!

2. Ogunquit, ME

Distance From Portland: 1 hour

Ogunquit is another one of the best options for day trips from Portland, Maine. It’s very close to Kennebunkport, and you can definitely do both in one day if you’re feeling up for it (although, there’s so much to do in each town that you can easily fill up a full day in each place).

Ogunquit is best known for having one of the longest stretches of sandy shoreline in all of Maine, so if you’re looking for a beach day without having to go far, this is one of the best places for that in Maine. Ogunquit’s town is also very quaint and easily walkable, and packed with adorable shops and great restaurants.

Some of the best things to do in Ogunquit on a day trip from Portland:

• Walk from Ogunquit’s town to Perkins Cove along Marginal Way for one of the most scenic walks in Southern Maine! Perkins Cove has its own town little town, so be sure to budget time to explore it.
• Visit the shops and restaurants downtown.
• Walk along the shoreline of Ogunquit Beach.

Bonus Suggestion : From Ogunquit, it’s also very easy to see Nubble Lighthouse on Cape Neddick, which is only about 20 minutes away, and is worth the excursion. Also close to York, which is home to some more beautiful scenery and the Stonewall Kitchen flagship store, this lighthouse lives on its own little island, and there’s a park that offers a fantastic view of the lighthouse for a gorgeous photo opportunity!

Psst! I have an entire post on things to do in Ogunquit if you need more ideas!

3. Portsmouth, NH

Portsmouth is a lovely little coastal town in New Hampshire that’s just over the Maine border, and only a short drive from Portland. Portsmouth’s downtown is so charming, and has a lot of really great shops, restaurants, cafes and breweries, as well as waterfront walkways, and even a small little lighthouse just outside of town. For all these reasons, it’s one of the best day trips from Portland, Maine.

Some of the best things to do in Portsmouth, NH on a day trip from Portland:

• Taste the local beer at these awesome breweries: Portsmouth Brewery , Loaded Question Brewing and Great Rhythm Brewing .
• Visit the cute shops in Market Square. Two of my favorites are Jane Gee for natural skin and body care products, and Sault New England for East-coast inspired clothing.
• Get some sweet treats at Elephantine Bakery .
• Stroll through Prescott Park.

If you’re looking to see as much of Portsmouth as you can, as well as take in some of the best water views, I recommend checking out this bike tour through town and the local islands . This is a guided tour that last about two hours, and is a casual cruise around town, as well as the surrounding islands. Led by a local expert, you’ll hear stories about the town’s history, as well as be able to stop for some awesome photo opportunities.

Click here to check out this bike tour in Portsmouth!

4. Boothbay Harbor, ME

Distance From Portland: 1 hour and 10 minutes.

One of my favorite small waterfront towns in all of Maine is Boothbay Harbor, and this makes for one of the best day trips from Portland, Maine. Even though it’s such a short drive away, you’ll definitely feel like you’re in a different world. Between the charming downtown, beautiful waterfront restaurants and amazing opportunities to tour the waters and see wildlife, you’re sure to have a great day in Boothbay Harbor.

Some of the best things to do in Boothbay Harbor on a day trip from Portland:

• Walk the streets of downtown to visit the shops and eateries.
• Cross the footbridge for views of town and the water.
• Head out onto the water for a wildlife and lighthouse tour (see my suggestions below!).
• Have an awesome waterfront lunch or dinner at Boathouse Bistro .
• Get an ice cream from Downeast Ice Cream Factory .

If you come to Boothbay Harbor for your day trip, I highly suggest you consider a boat tour. There are so many options in Boothbay, and the views are incredible. My favorite boat tours in Boothbay are the wildlife and lighthouse tours.

A great tour option for your day trip from Portland, Maine is the Lighthouses, Lobsters & Seals Tour . For the price, I think this tour offers a lot a fun and spectacular views. During this tour, you’ll pass by two lighthouses, spot seals lounging on the rocks, and also learn all about the local lobstering community, as well as what it takes to haul lobster traps. And with packing all that into only 1.5 hours, it allows you spend the rest of your day trip exploring the town.

Click here to check out the Lighthouses, Lobsters & Seals tour in Boothbay Harbor!

Another great option if you love lighthouses is this cruise along Kennebec River , where you’ll get to see 7 lighthouses, and also learn about the local maritimes and ship-building history. Tour guides will also help you spot shore birds and other wildlife during the cruise.

Click here to check out the Kennebec River Cruise!

Lastly, definitely consider this Puffin Tour during your day trip to Boothbay Harbor. This tour is about 2.5 hours, and takes you out to Eastern Egg Rock to see a puffin colony. During the tour, you’ll pass by lighthouses and gorgeous scenery, and the you’ll be guided by a member of the National Audubon Society to learn all about the puffins and other shore birds.

Click here to check out the Puffin Tour in Boothbay Harbor!

Psst! I have en entire post on fun things to do in Boothbay Harbor , which includes more tips for your puffin tour, so be sure to check out if you need more information.

5. Newburyport, MA

Distance From Portland: 1 hour and 15 minutes

Newburyport in Massachusetts is another one of the best day trips from Portland, Maine. I love visiting this little town because it’s both a gorgeous place packed with beautiful, colonial-style homes and quaint side streets, but also has a charming downtown, a waterfront park and even the stunning Plum Island to explore. You’ll definitely be able to fill up a full day here.

Some of the best things to do in Newburyport on a day trip from Portland:

• Stroll through the shops downtown.
• Walk along the paths in the waterfront park.
• Get lost in the charming residential side streets.
• Head out onto the water (see my suggestion below!).
• Explore Plum Island and the scenic trails at Parker River National Wildlife Refuge .

A great option for a boat tour in Newburyport is this cruise through the harbor on a Yankee Clipper . There are a few different tour options available, including a narrated history tour, a Parker River National Wildlife Refuge tour, as well as a sunset cocktail cruise if you want to end your day out on the water.

Click here to check out this boat tour in Newburyport!

Psst! I have an entire post on things to do in Newburyport and Plum Island , if you’re looking for more ideas for your day trip!

6. Sebago Lake, ME

Distance From Portland: 1 hour and 20 minutes

Sebago Lake is one of the best options for day trips from Portland, Maine if you’re looking for a peaceful day. While it’s a popular destination, it doesn’t often feel super crowded, and definitely has a very chill atmosphere. There are also a good amount of of kid’s activities here, including mini golf places, and lots of opportunity to get out onto the lake.

Since Sebago Lake is the second largest lake in Maine, it covers a pretty big area, and there are a few different towns that surround the lake, which each offer really fun things to do.

Some of the best things to do in on a day trip to Sebago Lake from Portland:

• Walk around the lake on the Outer Loop Trail inside Sebago Lake State Park.
• Rent Jet Skis and head out onto the water.
• Hike the trails at Hacker’s Hill Preserve.
• Grab some snacks, Maine whoopie pies and other delicious baked goods at Gemmes General Store.
• Eat fresh lobster at Stoney Brook Lobster Pound.
• Taste the local beer at Sebago Brewing Company

One of the best ways to get out onto the lake for a peaceful afternoon is by renting kayaks and spending a few hours enjoying the views from the peaceful water. Along with your kayak rental, you’ll get a life jacket, as well as a map of the lake so you know the best areas to explore.

Click here tochecko it this Kayak Tour on Sebago Lake!

7. Conway, NH

Distance From Portland: 1 hour and 30 minutes

A great option for a day trip from Portland, Maine is Conway, NH, which is located in the White Mountains region. While this is a great destination year-round, I think it’s especially enjoyable in the fall season to really take advantage of the fall foliage views. There’s actually so much to do in Conway that you probably can’t experience it all in a day, but it definitely makes for a great day trip to get some fresh mountain air.

This is also a great destination if you’re traveling with children, as there are lots of kid-friendly activities such as the Conway Scenic Railroad, roller coaster rides at Cranmore Mountain Resort and the Kahuna Laguna Water Park.

Some of the best things to do in Conway on a day trip from Portland:

• Explore the cute downtown and visit the shops.
• Visit all the waterfalls at Diana’s Baths.
• Drive or hike up to Cathedral Ledge View Point.
• Tour the local covered bridges.
• Get some sweet treats to bring home (or eat on the drive!) at one of the town’s many bakeries.
• Have a memorable meal at Chef’s Bistro.

8. Lake Winnipesaukee, NH

Distance From Portland: 1 hour and 45 minutes

Another great destination in New Hampshire that also makes for an awesome day trip from Portland, Maine is Lake Winnipesaukee, which is also the state’s largest lake. Mostly known as a summer destination, Lake Winnipesaukee is also a very scenic fall day trip because the amazing foliage colors.

Lake Winnipesaukee is actually comprised of eight different towns, each with something unique and fun to offer.

Some of the best things to do on a Lake Winnipesaukee day trip from Portland:

• Rent a jet ski or boat to spend the day on the water.
• Go ziplining at Gunstock Mountain Resort.
• Do a little shopping for unique finds at the Old Country Store in Moultonborough.
• Enjoy a ride on the Winnipesaukee Scenic Railroad.
• Visit the mountain top mansion Castle In The Clouds for awesome mountain views.
• Feel like a kid again at Weirs Beach, and ride the roller coasters, play arcade games and go kart.
• Go beer tasting at the local breweries (there’s quite a few here!).

One of the most fun tours to take in Lake Winnipesaukee is a ride in an antique boat ! During your day trip, you’ll want to consider booking a tour on the Millie B, where you’ll get to take in the spectacular views of the region, and maybe even spot a loon or two. With each tour on Millie B, guests get free admission to the Boat Museum as well.

Click here to check availability for your vintage boat ride tour on Lake Winnipesaukee!

9. Camden, ME

A great option to consider when looking at day trips from Portland, Maine is Camden. Camden is a beautiful town along the New England coast that has a really great Main Street with shops and restaurants, a really lovely waterfront park, lots of opportunities for sailing, an amazing state park with an incredible view point, and lots of coastal charm at every turn.

Some of the best things to do in Camden on a day trip from Portland:

• Drive or hike up Mount Battie in Camden Hills State Park for an awesome view of Camden Harbor from above.
• Visit the shops and eateries downtown and along Main Street.
• Walk along the waterfront to admire the gorgeous sailboats.
• Get a lunch picnic from Camden Deli and bring it to a picnic table at the water front park.
• Stop in Owl’s Head on your way there or back to visit the lighthouse (it’s worth the extra stop!).

One of the best things to do in Camden, though, is to head out on a sailing tour . Camden has some gorgeous vessels you can climb aboard, and you’ll have the opportunity to admire the landscapes from a unique perspective out on the water. This Windjammer tour is an awesome option, and they have two types of tours: one is a day sail, and the other is a sunset sail if you want to end your day out on the water. You’ll also be able to see Mount Battie and Curtis Island Lighthouse during either sail.

Click here to check out the Windjammer Daytime Sailing Tour in Camden!

Click here to check out the Windjammer Sunset Sailing Tour in Camden!

10. Boston, MA

Distance From Portland: 2 hours

Even though you’re coming from a city, Boston is always a good idea (at least, that’s just my opinion!). Boston is one of my all-time favorite cities because of its deeply-rooted history, gorgeous architecture, amazing restaurants and charming streets. While Portland also has a lot of that, I still think Boston is one of the best day trips you can take because the two destinations are different enough to make it worth your while.

Boston can easily be done in a day, and while you won’t see it all, you’ll be able to cover a lot of ground, depending on what you’re looking to do. And definitely don’t forget to make a reservation for dinner if you’re hoping for a special meal out!

Best things to do in Boston on a day trip from Portland:

• Stroll through the Public Gardens.
• If you like to shop, be sure to hit up Newbury Street and Copely Place.
• Explore the most charming streets in the Beacon Hill neighborhood (my favorite thing to do!).
• Grab a famous cannoli from Mike’s Pastry.
• Walk around one of the many waterfront parks.
• Get off-the-beaten-path at the Isabella Stewart Gardner Museum.

Best Boston Day Trip Tours

I highly recommend checking out a tour while in Boston, especially if it’s your first visit, or you’re looking to explore something new. Boston has so many amazing tour options led my local experts that share tons of tips and knowledge.

One great tour to consider on your day trip from Portland, Maine is a Freedom Trail Walking Tour . The Freedom Trail is one of the best things to do in Boston for history buffs (and anyone who wants to appreciate the country’s earliest years). You can definitely walk the trail yourself, and do the whole thing or just parts of it. But if you love history, consider this tour by a local historian to get even more out of your experience.

Click here to check out Freedom Trail History Walking Tour in Boston

For day-trippers, a Hop-on, Hop-off trolley tour is a great choice to cover more ground, and also learn something along the way. Once you get to Boston, I always recommend you park your car for the day and explore on foot, but a trolley tour will allow you to see more sites without having to worry about getting around a historic city in your own car.

Click here to check out the Hop-On, Hop-Off Trolley tickets in Boston

For foodies, definitely check out this North End Foodie Tour , which is led by a local culinary expert that knows all the very best spots. You’ll get recommendations for places to eat during the rest of your visit, and get to sample some amazing treats along the way like meats, cheeses, baked goods, drinks and pizzas. This is a walking tour, so you’ll also get to see some charming streets in the North End for a well-rounded day trip to Boston.

Click here to check out the North End Foodie Tour in Boston

How To Get From Portland, ME To Boston Without A Car

If you don’t have access to a car in Portland, you can take the Amtrak Downeastern train from Portland to Boston for your day trip. The best option is to drive because the train will take you three hours one-way, but if you don’t have access to a car, this is a great option!

11. Rockport, MA

Rockport is one of the best destinations for day trips in Maine if you’re looking to see one of the most charming and unique towns along the Massachusetts coast. It’s definitely my most favorite town in the North Shore region of Massachusetts, and probably one of my all-time favorite destinations in all of New England.

Rockport is small, but feels very special and memorable. The downtown area is packed with awesome and unique shops and eateries, there’s a big local artist scene here, and everywhere you go, you kind of feel like you’re in a postcard. It’s no wonder that Rockport has been used in a lot of movies!

Best things to do in Rockport on a day trip from Portland:

• Admire the most painted building in the U.S. – Motif 1.
• Stroll through Bearskin Neck and visit all the shops.
• Grab a lobster roll at Roy Moore Lobster Company.
• Walk on the Rockland Breakwater.
• Visit all the art galleries.
• Hit the trails at Halibut Point State Park.
• Kayak out to Thacher Island to see the lighthouse.
• Take a boat tour of the harbor.
• Get an ice cream at the cutest little ice cream shack on the East Coast!

Psst! I have an entire post on all the amazing things to do in Rockport to help you plan your visit!

12. Marblehead, MA

Marblehead is another amazing day trip from Portland, Maine. It often gets over-shadowed by the neighboring Salem (more on Salem later in the post, though!), but it’s definitely worth a full-day visit, or even a whole weekend. Marblehead has an awesome historic district with beautiful houses to admire, cute little shops and cafes, plenty of waterfront to explore and is even home to some Hocus Pocus filming locations!

Best things to do in Marblehead on your day trip from Portland:

• Explore Chandler Hovey Park and Marblehead Lighthouse.
• Visit Devereux Beach.
• Pick up some sandwiches and see what else you can find at Shubie’s Marketplace .
• Walk around Old Burial Hill Cemetery (a Hocus Pocus filming location). Be sure to find the gazebo at the top to admire the views.
• Grab a lobster roll at Little Harbor Lobster Company.
• Take in the views at Castle Rock.

Psst! I have an entire post on the best things to do in Marblehead, MA if you need even more ideas.

13. Gloucester, MA

Gloucester is a great day trip from Portland, Maine to consider, and is also only about 15 minutes from Rockport, so you can easily combine the two into one trip if you wanted. Both are excellent destinations to dedicate a full day to, however, so it’s entirely up to you!

Gloucester is packed with maritimes history, and also has lots of waterfront to explore. On top of that, though, you’ll find amazing restaurants, a quaint little downtown, a beautiful lighthouse and lots of tour options that get you out onto the water.

Best things to do on a day trip to Gloucester from Portland:

• Explore the Gloucester HarborWalk.
• Visit Hammond Castle to feel like you’ve been transported to Europe.
• Walk along the shore at Good Harbor or Wingaersheek Beach.
• Head over to Eastern Point Lighthouse and walk almost a half mile out on the breakwater.
• Have a lovely lunch at Sugar Magnolia’s.

One of the best places to go whale watching in the entire world (yes, world!) is actually right here in Gloucester, so this is definitely something you’ll want to consider for your day trip. Whale Watch tours from Gloucester head out to Stellwagen Bank, a national marine preserve that’s only 12 miles offshore. This particular tour is great for day-trippers because the vessel is a high-speed catamaran, so you’ll be able to cover more ground in the same amount of time, allowing you to really maximize your time.

Click here to check out this Whale Watching Tour in Gloucester

To get around Gloucester faster and easier, a great option for your day trip is to rent e-bikes ! E-bikes are so much fun to ride, and allow you to pack more into your schedule than just walking. And with e-bikes, you’ll be able to ride some of the bikes through all of Cape Ann since you’ll have them for 8 hours, allowing you to see even more of this gorgeous region.

Click here to check out renting e-bikes in Gloucester

14. Rangeley Lake, ME

Distance From Portland: 2 hours and 30 minutes

The furthest day trip from Portland, Maine is still definitely worth your time! Rangeley Lake in Maine is located in the Northwestern corner of the state, and is a beautiful destination to consider. And actually this region is home to several lakes, and covers a lot of ground, so you’ll have lots of options when it comes to towns to visit, activities on the water and places to eat. Rangelely Lake is also a quiet and peaceful destination, which makes for a wonderful escape from the city.

Best things to do on a day trip to Rangely Lake from Portland:

• Take a scenic drive along the Rangeley Lakes Scenic Byway.
• Cool down at the swimming holes at Small Falls.
• Enjoy the views at the Height of Land Overlook.
• Drive to the top of Quill Hill for more amazing bird’s eye lake views.
• Explore the charming shops in downtown Rangeley.
• Rent a kayak and head out onto the water.
• Have a lakefront dinner at the Loon Lodge Inn.

For something really fun and special (and a bit of a splurge that’s totally worth it), consider booking a seaplane tour over the region. This tour often spots moose from above on the lake shorelines, so if seeing a moose in Maine is on your list, this will be a great option. You’ll pass over two lakes and get to spot other wildlife as well. Even though it’s a splurge, the price is very fair for a private tour, especially in such a gorgeous area.

Click here to book your Seaplane Tour in Rangeley Lake!

Day Trips From Portland, Maine In the Fall

15. salem, ma.

Distance From Portland: 1 hour and 30 minutes.

Pretty much any destination in New England is wonderful to visit in the fall, but one of the best day trips from Portland, Maine in the fall is Salem, MA , especially during the month of October. I think Salem is a great town to explore year-round, but of course, there’s something extra fun and special about it in the fall season. From haunted tours, to fun street fairs, to a picture-perfect New England streets covered in leaves, this is one of the best day trips from Portland, Maine you can take during the autumn season.

One of the best tours in Salem is this Hauntings & History walking tour , and you can select either a day option, or a night option if you want to increase the spooky factor. The tour is led by a local historian and shares stories of the town’s incredible history, which dates back to the 1600s.

Click here to book your Hauntings & History Walking Tour in Salem!

If you’re a fan of the movie Hocus Pocus (and honestly, who isn’t?), then you may enjoy this walking tour of the movie’s filming locations in Salem. You’ll see five movie locations, learn some fun trivia about the movie, and also hear about the town’s fascinating history to get the best of both worlds.

Click here to book your Hocus Pocus Filming Locations Tour in Salem!

If you’re looking for a super spooky tour and lots of goosebumps, then you’ll love the Voodoo, Vampires & Ghosts Walking Tour . Done at night, this tour is led by a local history expert and takes you to some of the most haunted locations in town. You’ll also listen to authentic stories from the Salem Witch Trials and hear about ghost sightings around Salem.

Click here to book your Voodoo, Vampires & Ghosts Spooky Walking Tour in Salem!

Psst! I have an entire post on taking a day trip to Salem, MA , if you’re looking for more information!

Day Trips From Portland, Maine Without A Car

In all honestly, getting outside of Portland to explore the local areas without a car is very difficult, and sometimes not even possible. New England in particular really requires a car to get around, and public transportation between towns isn’t great, unless you’re going from one city to another.

But if you’re willing to stay in Portland, and head out for fun tours that will feel like day trips, this is an excellent option if you don’t have a car! Below I’ve also listed two options for companies that will drive you around Maine in a private tour if it works in your budget, and well as one tour in Portland that will feel like an escape.

Best Day Tours From Portland, Maine

A great option for day trips from Portland, Maine without a car is this full-day Maine in the fall tour . This tour will start at Portland Head Light, and take you out to Camden, Bangor and some of the best sites in Acadia National Park, including to the top of Cadillac Mountain and Bass Harbor Lighthouse. You’ll even have time to explore downtown Bar Harbor for a bit. This is a private tour for your group, and considering how much ground you’ll cover, the price for the whole group is very fair! Keep in mind that this is a fall-specific tour, and it’s not available year-round.

Click here to check out this full-day private fall tour from Portland!

If you’re willing to stay in Portland and explore the coastline, this awesome bike tour is 5-hours long, and will make you feel like you’re away from the city. You’ll head out to Cape Elizabeth, and explore the local lighthouses and dramatic coastline views, and also stop for an amazing lobster roll from a food truck that’s included in the tour cost.

Click here to check out this bike tour (with a lobster roll!) around Portland’s coast!

This company offers customized and private luxury tours throughout Maine, and if you’re looking to get around the state from Portland and don’t have access to a car, it’s worth reaching out to them to plan your perfect day trip.

Click here for more information on customized and luxury private day tours from Portland!

Can You Do A Day Trip From Portland, Maine To Acadia?

Yes, you can, but just keep in mind that it will be a long day and you’ll have to carefully plan what sights you really want to see and be strategic. Especially in the summer because of traffic and crowds. The drive is 3-hours one-way, but if your only opportunity to get to Acadia National Park is by taking a day trip, it’s definitely worth it!

There’s so much to do in Acadia that I usually recommend at least 2-3 nights, but you can also see a lot on a day trip. With a day, I would recommend doing Ocean Path (walking from Sand Beach to Otter Cliffs), one hike (Great Head or Gorham are both great choices), and then heading into downtown Bar Harbor for dinner before driving home. If your schedule allows, see if you can also do lunch at Jordan Pond House inside the park overlooking the mountains.

Here’s my guide on the perfect Acadia National Park itinerary if you need some day trip ideas, or are planning to spend a few nights there!

Hiking Day Trips From Portland, Maine

The destinations from this list that offer amazing hiking opportunities as a day trip from Portland would be Acadia National Park, Camden (Camden Hills State Park), Conway, Sebago Lake and Rangely Lake.

Day Trips From Portland, Maine In The Winter

Kennebunkport and Ogunquit are excellent options for days trips from Portland, Maine in the winter because of their holiday celebrations. The Kennunkport Christmas Prelude is one of the best Christmas festivals in New England, and Ogunquit’s Christmas by the Sea event will fill you with all kinds of holiday cheer. And since these two towns are so close to one another, you could easily combine them into one festive day trip.

Once the holiday season is over, a great option for a day trip from Portland, Maine in the winter is to head just a few minutes north to Freeport and explore the charming town covered in snow, explore the trails at Wolfe’s Neck Center & Farm and then head back into town for a very cozy meal at Tuscan Brick Oven Pizza.

Conway, NH from this list is also an awesome day trip in the winter. Known as an incredible ski destination, you’ll be able to hit the slopes, or just enjoy the quaint town and its attractions covered in a beautiful blanket of snow.

More Of My Maine Travel Guides:

• Maine In November: Is It Worth Visiting?
• Maine In The Spring: Where To Go & What To Do
• Maine In October: Best Fall Foliage Spots & Things To Do
• Maine In The Winter
• Portland, Maine In The Winter
• Best Stops To Make On A Portland, Maine To Acadia National Park Road Trip
• Best Breweries In Portland, Maine
• Where To Find The Best Whoopie Pies In Maine
• The Best Maine Lighthouse Road Trip Itinerary
• Blueberry Picking In Maine
• My Unforgettable Boston To Bar Harbor, Maine Road Trip Itinerary
• Maine In The Summer

You may also enjoy:

• Best Christmas Towns In New England
• Best Day Trips In New England
• The Most Incredible New England Lighthouses To See

That’s A Wrap On The Best Day Trips From Portland, Maine

Now that you know all about the best day trips from Portland, Maine, you’re armed and ready to plan your own perfect day. Whether you’re excited to head to Boston and relive history and enjoy the amazing culinary scene, or you’re looking forward to a quiet day at one of the best lakes in the region, the opportunities for seeing amazing landscapes and taking some awesome tours are endless. Happy planning!

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Portland Maine Itinerary | Perfect For A Few Days

Maine has a favorable reputation of being a wonderful place to visit. This tucked away New England state has become even more popular in recent years and really is a great place to vacation. My sister and friend came to see us while in Portland making it even more special. We had a few days packed full of activities from shopping, exploring, eating, drinking, tours and time on the water. So if your looking for ideas on the perfect Portland Maine Itinerary, we have lots of ideas for you!

Disclosure: Some of the links below are affiliate links. This means that, as an Amazon Associate or other affiliate, I earn a small commission from qualifying purchases.

What to expect from Portland Maine

Portland is Maine’s largest city, and it was the first stop on our tour of Maine. (Our Maine stops include Portland, Freeport, Boothbay, Camden, Belfast, Acadia and Bar Harbor). 

Portland is actually a peninsula with water views on three sides from Old Port to West End and East End. It is a city without tall building (no more than 175 feet) and no billboards. This is a Maine state rule to preserve the beauty and protect the views. Therefore maintaining Portland’s small town feel even though its Maines largest city.

The city offers many things to do. You can choose from a variety of indoor activities such as great restaurants, coffee shops, best breweries, historic buildings, art galleries and museums. Or try some outdoor activities such as relaxing on sandy beaches, enjoying a scenic drive, exploring walking trails or being on the water.  

Portland Maine has activities for everyone. So after we spent a week exploring downtown Portland and the surrounding area, these are my recommendations. So, here you’ll find the best places to add to your Portland Maine itinerary.

Where is Portland, Maine

Portland is located in lower Maine on the Atlantic coast. Maine borders New Hampshire and specifically Portsmouth along the east coast.

If you’re driving into Portland, the nearest highways are I95 and I295. These are the driving distances from nearby cities: 

• from Boston MA 107 miles 
• from Montreal Canada 256 miles
• from Manchester NH 95 miles
• from Bar Harbor ME 175 miles

If you plan to fly into Maine, then you have a few options. You can fly into Portland International Jetport, Manchester NH, or Boston MA. Sometimes you can find better deals by flying into MA or NH and driving in. 

Having a car in downtown Portland is not necessary, however if you want to explore beyond that, I would recommend a car.  

Best time to visit Portland

Maine has four seasons: June, July, August and winter. Well, that’s what we were told on our trolly tour. But all joking aside, Maine winters are cold. So the best time to visit is between late spring and early fall. 

Summer months have the best weather but also the most crowds.

After Labor Day in September and October are considered shoulder season and temperatures are still pleasant with less crowds. 

Anytime during these months, should be a nice visit. So with that being said, lets talk about the best things to do for a Portland Maine Itinerary.

Ideas for a Portland Maine Itinerary 

1. make a stop in kennbunkport .

If you are driving into Portland, then you have to make a stop at Kennebunkport along the way. This cute coastal town is how you image small towns in Maine must look: waterfront, historic, charming with fresh seafood everywhere! And Kennebunkport is no exception.

Our group only had a few hours in Kennebunkport, and could have definitely spent more time. We walked around the shops and had a delicious dinner. We ate at The Boathouse Restaurant where we sat outside with waterfront views.

Kennebunkport is a great option to experience small town Maine.

Did you know Walker’s Point Estate (or the Bush compound) is the summer home of the Bush family, in the town of Kennebunkport, Maine. So, yes, its a nice place!  

2. Visit the Old Port District

If you like shopping, historic buildings, craft beer, delicious food and especially lobster rolls, then you will love Portland. It’s a fun city!

Geographically the Old Port District is bordered by Franklin Street (U.S. Route 1A) to the east, Commercial Street to the southwest by the water, and 19th-century buildings to the north.

The Old Port is also surrounded by the neighborhoods of Bayside, East Bayside, Munjoy Hill and the West End. However most of the action in Old Port is on Commercial Street, Fore Street, Exchange Street and at night, Wharf Street. 

Below are all great ideas in within Old Port to add to your Portland Maine itinerary:

Explore local shops and art galleries 

Did I say shopping? There are so many great shops in Portland. So if you like to shop, you found your spot other than driving to Freeport.

Explore Portland’s boutiques and specialty stores for one-of-a-kind finds, including handmade crafts, vintage items, all things lobster, whoopie pies and more.

You will also find numerous art galleries and pottery stores. 

I purchased some red lobster lollipops for my sister to take back to my nephews. They loved them!

Indulge in a potato donut at Holy Donut

We always like to find tasty treats in new places. So when I heard about Holy Donuts and their potato donut, well I knew we had to give it a try. It definitely has a different texture from regular donuts.

In my opinion, the potato makes the donut more dense and therefore more filling. The donuts are big in size and I recommend getting one with a flavorful frosting. If you like unique sweet treats, give it a try!

They also have vegan and gluten free options.

Donut Tours are also available in the city. So if you want to learn more about donuts and visit other donut shops around Portland, you might consider one.

Dine on delicious fresh seafood

The food scene in Portland is really good. There are many well rated restaurants in the downtown area. Almost too many to mention.

I will say this, if you have a place you really want to eat at, then make a reservation in advance. With our group of 4 the wait time at the best restaurants like Central Provisions was over an hour. 

The city is full of great options for a lobster roll, clam chowder, fresh oysters and other ocean-inspired dishes.  

A really fun place for lobster rolls or lobster on a stick is The Highroller Lobster Co . This diner style restaurant started off as a food truck and has continued to grow and expand ever since! 

Culinary Tours are also a popular option to experience what the city has to offer from seafood, cheese and more.

And if at the end of your trip you can’t eat any more lobster and you just want some pizza. Give Pizzaiola a try. After our sunset trailing trip, we all had a slice, and it totally hit the spot!

Drink craft beer from local breweries

Portland is a hub for craft beer. It has the more craft breweries than any other US city. So for all the beers fans out there, get ready to do some tasting. 

There are many local breweries just a short walk from each other in downtown Portland. Offering a variety of beer selections such as pale ales, fruit beers, sours, belgian-style beers and many others.

Here are some popular ones to visit, but its just a short list, as there are many more!

• Shipyard Brewery Company 
• Allagash brewing Company
• Bissell Brothers Brewing Company
• Sea Dog Brewing Company

We enjoyed a great beer flight at Shipyard Brewery Company and loved Portland Mash TUN on Wharf Street for a cool vibe tavern offering a variety of local craft beer. 

You an also opt for a guided brewery tour .

There are many ways to taste your way through Portland!

Walk down historic Wharf Street 

Wharf Street comes to life at night. This cutest of cobblestone streets is a narrow, almost alley way street. It is pedestrian only during the summer months, that way you don’t have to worry about cars when its busy.

This street represents Portland’s rich history and lively present. So even if you’re not dining along the street, you should at least walk down it. That way you can experience some of the history and the ambiance of this high energy street.

PARKING TIP : Parking in Portland is both expensive and can be hard to find. We found two affordable lots, so if you’ll be spending more than 4 hours in town, they are worth it. 

• One lot is only $5 for the day, with a little further to walk at 450 Commercial Street  
• The other lot is $20 for the entire day located near the pier at 2 Commercial Street

Take a trolly tour around town 

This was our first time in Portland, so we were unfamiliar with the city layout and neighborhoods. Therefore we decided to take a trolly tour to get acquainted with the city.

The trolly tour has two options: Tour with Lighthouse or Tour without the Lighthouse . So, if you plan to visit the lighthouse on your own, then opt for the NO lighthouse tour. 

On the trolly, you will see many areas of the peninsula. It gives you a nice overview of the city and then you can decide if you want to come back and experience more. Here are some highlights of things you will see and can do later:

Walk the Eastern Promenade

With beautiful views of Casco Bay, this is the perfect place to enjoy outdoor activities. You can walk or bike along the 2.1 mile Eastern Promenade trail that connects to downtown.

At the park you can plan a picnic, enjoy East End Beach or just relax and take in the scenic views. Its a beautiful 68-acre historic landscape, worth a visit. The perfect place for a morning walk or afternoon stroll. 

Visit the Portland Art Museum

For the artists at heart, immerse yourself in art at the Portland Museum of Art located in the Arts District of downtown Portland.  

Known for being the oldest and largest art institution in Maine, the museum features an impressive collection of American, European, and contemporary works.

It is closed Monday and Tuesday although open throughout the year.  

Tour the Victoria Mansion 

Tour the lavish Victoria Mansion , a National Historic Landmark that showcases stunning architecture and interior design from the mid-1800s. The mission is to conserve, maintain and restore, as the house still has over 90% of the objects that were in the house in 1860.

Tickets available from May 1 to October 31 with advance tickets recommended.

Climb the Portland Observatory 

For panoramic views of the city and the harbor, climb to the top of the Portland Observatory , a historic maritime signal tower.

So, if you would like to see a birds eye view of the city, you should plan to visit. 

Open seasonally with guided tours offered Thursday to Monday and self-guided tours on Saturday.

As you can see, the Old Port District is full of fun things to do. However, if your looking for a more quintessential Maine small town feel, then you may want to consider adding smaller cities into your travels too. 

Portland Maine Itinerary outside of Old Port District

4. enjoy beautiful views of the portland head light .

Just a few miles from downtown, in Cape Elizabeth is the Portland Head Lighthouse. This iconic lighthouse one of the oldest lighthouses and also one of the most photographed lighthouses in the United States and for good reason. 

With breathtaking ocean views, historic surroundings and scenic walking trails the park is both beautiful and peaceful.  Because the park is so nicely landscaped, you really just want to hang out and enjoy it all day. We walked the cliffside path and enjoyed views of the lighthouse from both directions. 

With 90 acres of space, Fort Williams Park is the perfect place to spend an afternoon. And being an outdoor and nature lover, this was one of my favorite things to do. 

The park is free to visit, you only pay for parking and a small fee to tour the museum. Food trucks are also onsite if you need lunch or a snack. 

There are 5 other lighthouses nearby to visit including Bug Light Park and Spring Point Ledge Lighthouse. 

5. Spend time on the water

Downtown Portland is located on the water. And that means there are lots of options when it comes to water activities. So whether you want to learn about lobsters, search for whales, relax on the water or head over to a nearby island, there is an activity waiting for you. 

So for your Portland Maine itinerary, make sure to include some time on the water.

Lucky Catch Cruises

If you like lobster and looking for a totally Maine experience, then check out Lucky Catch Cruises. This 1.5 hour lobster tour cruises the harbor while you get a hands on lobster fishing experience. And as you can see they go out rain or shine! Unfortunately Scott and I had to postpone our tour and got the rain.

At the end of the tour, you will know how to trap lobster, be able to determine the sex, learn how they protect against overfishing, and purchase a fresh lobster for lunch or dinner.

The experience was more informative rather than adventurous, however, we really enjoyed it.

Whale Watching Tour 

There is something magical about whale watching. And if you’ll never experience it, you definitely should. 

In Maine, whale watching season is mid April thru October. So if you visit during these months, You will have the opportunity to see humpback, finback, mine and pilot whales. Try to pick a clear sky day, because Maine’s fog will take away your visibility to spot the animals. 

The Odyssey Whale Watch Tour is 4 hours and they go out about 15 miles looking for whales. While there is never a guarantee for seeing whales, it is highly likely to spot a few in season.

Sail the harbor in a Schooner

Another great way to get on the water is a 2 hour Windjammer cruise. Sail around the Casco Bay and enjoy the views of picturesque lighthouses, the rugged Maine coastline line, spot a harbor seal and just relax. 

We went on the Portland Schooner sunset sail and even though it was cloudy and lacked a sunset, the sail was very relaxing and enjoyable. Its BYOB, so you can enjoy a beverage while sailing around.

It was a great evening on the water sipping wine with friends and family. 

Take the ferry to Peaks Island 

Maine has so many small islands off the coast. So, if you’re curious about them, take the Casco Bay Ferry and explore the nearby Casco Bay Islands. 

Peak Island is the most populated and makes a fun day trip. On the island you can bike, hike and enjoy the stunning coastal landscapes. We didn’t get a chance to visit. However, we did get a peek from the water on our schooner sail. 

Kayak the salt marshes 

We stayed just outside of Portland in Scarborough. Nearby our campground was Scarborough Marsh Audubon Center. Little did we know, this is the largest salt marsh in the state. We rented a kayak and spent about 2 hours on the water paddling out and back. It was fun, even though we got caught in the rain. 

Maine’s tidal elevation change is around 8 feet or more. So, make sure you watch the tide chart because at low tide, there is not enough water to paddle through.

6. Day trips for your Portland Maine itinerary

Want to experience Maine outside of its largest city? Consider a little day trip outside of the Portland area. These are some other places we visited:

Freeport 

The small town of Freeport is less than an hour away. With a plethora of outlet stores, this small town is also home to the LL Bean flagship store.

LL Bean has a great story and continues to offer exceptional service to its customers. As the stores are open 24 hours a day. That’s right, they never close. So if you feel like late night shopping, its available. 

Boothbay Harbor

Just a little over an hour away, this Mid-Maine coastal town is small and charming with a harbor side downtown. Boothbay is another classic seaside Maine town with a chill coastal vibe, fresh local seafood and quintessential clambakes.

Camden 

Another really cute coastal town is Camden. It is a place where the mountains meet the sea, with a charming downtown, historic architecture and scenic mountain hilltop views.  

Acadia National Park 

While not recommended as a day trip, it is as a side trip. Acadia National Park is by far the most popular national park in Maine. And a great place to visit.

However, if visiting another small city is not on your agenda. You can still explore outside of Portland by visiting a blueberry farm, apple orchard, maple sugar house or even a vineyard. 

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In conclusion.

As you can see, the Portland area has so many fun things to do! From a day trip, long weekend or week long stay. Portland is full of activities from land, sea and sport. 

So whether Portland is your final destination or part of your road trip, this Portland Maine itinerary will help you discover the best parts of town.

Enjoy and have fun on your Portland adventure!

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Meet Kim, a spirited adventurer and full-time RV traveler who, along with her partner and small furry companion, is on a perpetual journey to explore the wonders of the open road. With a passion for wanderlust, Kim has embraced a nomadic lifestyle, making her home on wheels as she crisscrosses the country in search of hidden gems and breathtaking landscapes.

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3 Days in Portland, Maine: The Perfect Weekend Itinerary

Portland , Oregon , tends to be the more famous of the two Portlands, but for Mainers, Portland , Maine , is the big city. Filled with rich history, scenic parks, and an incredible food and drink scene, this Portland more than deserves a trip.

If you’re planning a 3-day weekend in Portland, Maine , you’ll likely want to arrive between late spring and early fall. Although summer is the peak of tourist season, you’ll find that much of Portland shuts down when the weather turns cold. So many of the top attractions in the city may not be open if you arrive later in fall or winter.

Plus, with Portland being a coastal city, you’ll likely want to take advantage of the beautiful coastline and nearby islands when the weather is nice enough. And summer is also when you’ll find the most events and festivals. June brings about Portland Wine Week , while nearby Yarmouth holds its annual clam festival in July, and you can enjoy the famous Maine lobsters at their own festival in nearby Rockland in August.

Planning a weekend in Portland? We’ve put together a Portland itinerary to help you see the very best of the city in just three days. Stick to this list, and you’re bound to have an incredible time on your coastal getaway!

Please keep in mind that this Portland, Maine, itinerary assumes that your three days in the city begin on a Friday, as there are time-sensitive activities on this list. The Portland Museum of Art is not open on Monday, and therefore, you cannot visit this stop if your last day is Monday. Additionally, the farmers’ market, which you’ll see on your second day, is only open on Wednesdays and Saturdays. 

If you’re still deciding where to stay then make sure to check out our article on the  cool boutique hotels in Portland, Maine !

Disclaimer: This post may contain affiliate links. If you make a purchase or booking through one of our links we may earn a small commission (don’t worry, it’s at no extra cost to you).

How to Spend a Weekend in Portland, Maine

Getting around portland.

If you’re arriving in Portland via plane, the most convenient airport is the Portland International Jetport , not to be confused with Portland International Airport, which will take you to the other city of the same name in Oregon. The Portland International Jetport is just 2 miles from Downtown Portland, making it easy to start your 3-day weekend in Portland, Maine, when you arrive here.

From there, you have several options. To start your trip, you can take Route #5 of the METRO’s bus service to get to the downtown area. If you choose to rely on public transportation during your 3 days in Portland, you’ll be taking the METRO quite a bit, as it makes it easy to get to many of the top destinations in Portland. 

However, it’s worth considering getting a rental car in Portland. While you won’t need it to get around the downtown area, you may want it if you plan on venturing further out. Uber and Lyft do operate in Portland, but service can be spotty and slow. Plus, taxis aren’t always easy to find. So, if you’re without a rental car and want to go somewhere that’s difficult to get to with public transportation, you may be waiting for a while to get a ride. 

If you have more than 3 days in Portland, you should definitely consider getting a rental car, especially if you want to venture outside of the city proper. Portland has many day-trip options. If you want to visit a major city, Boston is under two hours away by car, but you can also check out smaller cities with unique offerings. 

Rockland in Maine, for instance, is a great place to visit for its quaint arts scene, while you can’t beat Salem in Massachusetts if you’re visiting during the spooky season. And Acadia National Park is only 3 hours away by car for those looking to experience scenic hiking and other outdoor adventures.

Explore Portland on a Trolley Tour

Portland, Maine Itinerary – Day 1

Explore old port.

You’re going to start your 3 days in Portland, Maine, at the heart of the city, the Old Port. Here, you’ll find cobblestone streets that will transport you back in time as you venture past 18th- and 19th-century buildings that now house some of the best dining, drinking, and other attractions you’ll find in Portland. 

Breakfast at The Holy Donut

Before you get started exploring, you’re going to need to fuel up. And we can’t think of a better way to do it than by chowing down on one of the best doughnuts in the Northeast, which can be found at The Holy Donut . 

These massive doughnuts are made with potatoes, making them rather hearty and filling. If you can only eat one, we highly recommend the Maple Bacon, the Blueberry Holy Cannoli, or the Honey Lavender. Or you can buy all three and split them with your fellow travelers because, trust me, these doughnuts are too rich to try and eat three at a time by yourself!

Learn All About Maine Lobsters on a Cruise

Next up, you’re going to do something that you can only really do in Portland. Maine is famous for its lobsters, so you’re first activity is to learn just where they come from. Lucky Catch Cruises offers the chance to climb aboard a lobster boat and see it in action. Keep in mind that this cruise tends to sell out, so be sure to get your tickets in advance.

You’ll venture out on the waters of Casco Bay, where you’ll be guided through the day-to-day of a real Maine lobsterman. How much you participate is up to you. You can just enjoy taking in the sights, or you can help haul up the traps yourself. 

No matter which you choose, you’ll also get to enjoy listening to a knowledgeable guide who will tell you all about the history of Maine’s lobster scene, today’s conservation efforts, and little-known facts about your favorite crustacean!

Once your cruise comes to an end, you have the option to buy the lobster you catch at a reduced price than what you’ll find elsewhere. Didn’t catch anything? No problem. 

The tour company also keeps a fresh supply for visitors, just in case. If you do decide to purchase one, you can bring it home to cook yourself, or you can turn the lobster into your lunch by venturing over to the Portland Lobster Company , where they’ll cook it up for you. 

Didn’t buy a lobster? We have another great lunch option for you. Stay in Old Port and head on over to Duckfat . If you’re a poutine fan, you’ll hardly find a better place for it than this local favorite. 

The gravy is made from scratch with roasted duck bones, while the cheese curds are locally made. No matter if you’re getting the poutine or simply an order of their incredible fries, they’re always made in true Belgian style and fried in the restaurant’s signature duck fat. 

Discover the Best of Portland Food

Go Brewery Hopping

Hopefully, you didn’t fill up too much because your next activity is a tour of Portland’s famous brewery scene . Did you know that Portland has the most breweries per capita of any US city? It has 18 breweries for every 50,000 people. For some comparison, the other Portland, which is also considered a top place for brewery lovers, only has nine for every 50,000 people. 

Maine Brews Cruise can help you see some of the best breweries Portland has to offer. If you want to stick around Old Port, you can take their Old Port Walk, Talk, & Taste Tour, which is as focused on the craft beer scene as it is on Portland’s history. While you stroll along with your guide, you’ll learn about important Portland landmarks, like the US Custom House, the Workingmen’s Club, and the Mariners’ Church. 

From there, you’ll make your way to three of Portland’s top breweries: Shipyard Brewing Company , Gritty McDuff’s , and Liquid Riot Bottling Company . Included in your ticket price are samples of craft beer and hard seltzer at the three locations, as well as a snack at one location.

Visit Portland’s Breweries

Go Shopping in Old Port

Depending on when your tour is, you should either do some shopping around Old Port before or after. Old Port is filled with charming boutiques and storefronts, especially if you want to experience Portland’s food scene. Over on Fore Street, you’ll find the Old Port Candy Co. , famous for its fresh fudge and chocolate. It’s a must-do on any Portland, Maine, itinerary if you have a sweet tooth!

Or, for an even more unique option, visit Washington Avenue’s Onggi Ferments + Foods . This market, bakery, and cafe specializes in all things fermented, believing deeply in the health and flavor benefits of fermentation. Whether you want to learn to ferment yourself or just want to chow down on some fermentation-forward treats, like sourdough chocolate chip cookies and matcha and black sesame butter mochi, Onggi is worth a stop. 

Dinner at Eventide Oyster Co.

When you’re ready for dinner, head over to Eventide Oyster Co. Hopefully, you’re not too lobstered out from your morning cruise to enjoy Eventide’s famous brown-butter lobster roll. But if you are, there’s plenty more to enjoy at this oyster bar.

You’ll find oysters aplenty on this menu, as well as many more seafood options. From clam bakes to their signature scallop waffle-yaki, there’s so much to choose from. The same goes for their extensive drink menu. The hardest part of eating and drinking here is trying to make up your mind on what to order.

Portland, Maine Itinerary – Day 2

Visit the portland farmers’ market.

Start the second day of your weekend in Portland, Maine, feeling like a local by visiting the Portland Farmers’ Market . Held in Deering Oaks Park, this farmers’ market is where you’ll find over 40 of Maine’s best farmers and food producers. 

From fresh berries and oysters to cheese and maple syrup, there’s a little bit of everything to try here. Sample your way around the market and help support local farmers in a beautiful setting. 

If sampling the market’s treats didn’t fill you up, take a short stroll over to the Bayside American Cafe , a cozy spot that’s famous for its brunch offerings. From homemade corned beef hash to buttermilk pancakes stuffed with cheddar, bacon, and scallions, Bayside turns classic American breakfast dishes into new and inventive options that are bound to leave you stuffed and satisfied. 

If you’re an eggs benedict fan, you have eight different variations to try, from a Cajun-inspired benedict to one served with famous Maine lobster. Don’t forget to grab yourself one of their innovative cocktails to go alongside your breakfast!

Tour the Portland Observatory 

From there, catch a bus or enjoy a leisurely walk to the Portland Observatory , a historic landmark that offers one of the most incredible views of the city. The 86-foot octagonal tower was built in 1807 and is today the last remaining maritime signal town in the US. 

You’ll find the tower over on Congress Street, where 45-minute guided tours run every half hour from Thursdays through Mondays. On your tour, you’ll be able to climb the long and winding stairs to the top. 

There are just over 100 steps to climb, and there is no elevator to reach the top, so this activity may not be an option for those unable to make that trek. But if you can reach the top, the view is well worth it.

Lunch at Navis Cafe

For lunch, stop by Navis Cafe , which offers hearty sandwiches and all-day breakfast options. From lobster rolls to ham, egg, and cheese bagels, it’s comfort food at its finest. Grab a cold brew or a craft beer and make yourself at home in this cozy cafe. 

Explore the Maine Narrow Gauge Railroad Co. and Museum

Just a short stroll away is the Maine Narrow Gauge Railroad Co. and Museum . This unique museum focuses on preserving the history of Maine’s railroading heritage. But it’s much more than a museum.

Here, you can take a ride in a vintage train car, enjoying the beautiful scenery sweeping past you. Your journey also includes onboard narration that will tell you all about Maine’s railroading history, as well as the history of the landmarks you’re going past. 

Since you’re visiting on a Saturday, you can take the Sunset Express, assuming you’re planning your weekend in Portland in the summer. On summer Saturday evenings, the Sunset Express allows you to take in the usual route with all its beautiful sights, with the added benefit of seeing it all as the sun begins to set. 

Plus, all passengers get a complimentary beverage. Adults can partake in craft beer, hard seltzers, or wine, while little ones also get their pick of alcohol-free drinks.

Dinner at The Front Room

For dinner, head over to The Front Room , a true Portland hidden gem. This neighborhood gathering spot is quaint and comfortable, almost as comfortable as the comfort food on the menu. From burgers to carbonara to duck breast, there’s a little bit of everything on the menu, so you can guarantee that every member of your party will find something to fall in love with.

Portland, Maine Itinerary – Day 3

Breakfast at two fat cats bakery.

To start the last day of your 3 days in Portland, Maine, you’re going to visit one of the best bakeries in the city: Two Fat Cats Bakery . This shop specializes in fresh baked sweets made with real butter, local eggs, and other locally-grown ingredients. Stop in for breakfast and help yourself to a delicious treat, like their Blueberry Buckle, a New England-style cake-like pastry made with wild Maine blueberries and a brown sugar and oat streusel topping. 

Is it too early for a whoopie pie? We’re inclined to say the only acceptable answer is: “Never!” It’s never a bad time to get this classic Maine dessert. If they’re available, be sure to get one of their whoopie pies. 

The traditional one comes with two moist chocolate cake rounds with vanilla buttercream sandwiched between. But there are also seasonal options, like their lemon zucchini cakes with wild Maine blueberry filling. You absolutely can’t leave Portland without getting yourself a whoopie pie.

Peruse the Portland Museum of Art

Now, you’re fueled up to start your day, so stroll on over to the Portland Museum of Art . As the oldest and largest art museum in Maine, they claim that it would take you nearly 10 years before you could see everything in their collection. While you don’t have 10 years and you only have 3 days in Portland, you should still stop in to see all that you can. 

The museum’s permanent collection includes everything from American and European artwork to pottery and silverware collected throughout time. You’ll find both local artists on display, as well as works by some of the greatest artists of all time, like Claude Monet and Winslow Homer.

This museum also hosts numerous events, so you never know what will be going on when you visit. From film screenings to artist talks to workshops, a morning at the Portland Museum of Art is always well spent.

Lunch at Artemisia Cafe

Next, get lunch at the Artemisia Cafe , which serves brunch until 2 pm on Sundays. Their menu is packed with traditional brunch favorites done right. 

If you’re in the mood to go the breakfast route, you can choose between options like French toast, breakfast burritos, and vegetarian hash. If you’re more in the mood for lunch, you can dine on burgers, salads, and sandwiches. Or get the best of both worlds with the egg-topped Brunch Burger.

Go Back in Time at the Victoria Mansion

Your next stop is a historic landmark you’re not going to want to miss. The Victoria Mansion was built between 1858 and 1860 and is considered one of the best-preserved examples of pre-Civil War architecture in the US. 

Though the outside is stunning, you can also venture inside, where you’ll see the hand-painted murals, marble fireplaces, and intricately-carved woodwork throughout. Ninety percent of the original furnishings are still on display, which really helps transport you back in time.

If you decide to take a guided tour, they run every 20 minutes, with tours lasting between 45 and 55 minutes. While some days offer self-paced tours, other days only allow docent-led tours, so you may have to take a guided tour on the day you visit. 

Be sure to purchase your tickets in advance and check the website’s calendar to learn if you’re visiting on a day when you’re allowed to do a self-guided tour or if you’ll need to take a docent-led tour.

Admire Victoria Mansion

Set Sail with Portland Schooner Co.

After you tour the mansion, venture back to the Old Port region for the last activity of your weekend in Portland. The Portland Schooner Co. offers sails on a Maine-crafted wooden schooner. 

While you will have a knowledgeable captain and crew to guide you, there’s no narration, and it isn’t so much a tour as it is simply a relaxing, scenic experience. You’ll be able to sit back and enjoy the ride as you watch the coastline go by. 

The company has two-hour-long sails throughout the day, but it’s hard to find a better time to go out on the water than at sunset. Their sunset sails occur as early as 4 pm or as late as 6 pm, so be sure to check the website to make sure you don’t miss your departure time.

Dinner at Street & Co.

Next up, grab dinner at Street & Co. over on Wharf Street. You already know that lobster is famous in Maine, but did you know that scallops are another specialty? Street & Co. is where to get some of the best scallops in Portland. 

This bistro-style restaurant is all seafood, all the time. All ingredients come from local fishermen and farmers. If you’d rather skip the scallops, you can also get lobster here, as well as mussels, clams, shrimp, and many different kinds of fish. 

The restaurant also has one of the best wine and cocktail lists in the city, and their innovative dessert menu is delightful. Their Limoncello Mousse makes for a great way to end your weekend in Portland, Maine!

More Places to Eat & Drink in Portland, Maine

Drink and play at Arcadia : Named for the Acadia National Park, this arcade bar is perfect for date night. Share some cocktails while you challenge each other to beat your pinball scores. There’s even a monthly board game night if you’re more into analog fun.

Try Maine classics at Fore Street :

Made with only local ingredients, the dishes on this upscale restaurant’s menu change daily depending on what’s in season and what the local farmers, fishermen, and foragers can provide. But it’s always serving Maine favorites, like oysters and mussels.

Split small plates at Central Provisions :

This rustic restaurant is designed for groups to share both food and drinks as well as conversation. You’ll find plenty of unique offerings on the menu, like pear wine and sheepmilk cheese.

What to Do If You Have More Than 3 Days in Portland, Maine

Eastern promenade trail.

Walk along the Eastern Promenade Trail. The Eastern Promenade is a scenic 68-acre park right on the waterfront, featuring several hiking and walking trails. The Eastern Promenade Trail was an old railway line that’s easy to follow and takes you right through the heart of the park.  

Cape Elizabeth

See the lighthouses in Cape Elizabeth. Cape Elizabeth is home to stunning views, a tranquil beach, and two of Portland’s most well-known lighthouses. The Two Lights and the Portland Head Light are each famous in their own right, though the latter is actually the most photographed lighthouse in the world! 

See the Lighthouses of Portland

Peaks Island

Take the ferry to Peaks Island . Portland is surrounded by small islands, with Peaks Island being the most popular of them. Hop on the ferry and then spend the day enjoying the island’s beaches, galleries, and museums.

Mailboat Run

Take the Mailboat Run . The Mailboat Run offered by Casco Bay Lines is a ferry that delivers mail to the islands around Casco Bay, and it’s one of the most unique things to do around Portland. It’s also a great way to see the other islands outside of Peaks Island.

Acadia National Park

Visit Acadia National Park . About 3 hours away by car, Acadia is one of the best day trips from Portland. There’s a reason why it’s one of the top 10 most visited national parks in the US. Here you can go hiking, biking, stargazing, tide-pooling, kayaking, swimming, and see historic landmarks.

Discover the Best of Acadia National Park 

We hope you enjoy your weekend trip to Portland, Maine! Should we add something else to our 3-day Portland, Maine itinerary? Let us know in the comments.

Planning a trip to Maine? Check out our favorite travel guides and resources!

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About the Author:

Jacqueline is a writer and editor pursuing the freelance life to explore the world. Born and raised in New Jersey, she spent her college years in Boston before settling down with her partner and puppy in Monterey, California. When she’s not writing, you can often find her planning her next trip. Road trips are her favorite, whether it’s driving across the country or simply exploring a new city in her own backyard. She loves uncovering the history of every new place she goes. Jacqueline has a restless passion for learning and makes it a goal to pick up a new skill every year. She’s picked up embroidery, crocheting, knitting, and cross-stitching, but she’s hoping to master more languages to help her in her travels. She’s also a published author, with short stories and poetry appearing in several anthologies.

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A Long Weekend Portland, Maine Itinerary for 4 Days

A New England road trip itinerary must not exclude Portland, Maine . This coastal city is on a scenic peninsula along the Casco Bay in Southern Maine. It’s a beautiful destination to visit during the warmer months and offers picturesque fishing wharves, the best seafood restaurants, old-world charm, microbreweries, lighthouses and memories to be made.

Overall, the state of Maine is known for its lighthouses; six are within a half-hour drive of Portland ! There are also 3,100 off-shore islands in Maine, including the picturesque Casco Bay Islands off Portland.

I’ve been to Portland, Maine twice and believe it’s an underrated city in the United States that deserves more recognition. The times I visited were during Memorial Day Weekend in 2017 and on a fall trip in October 2023. Visiting Portland between May through October is best because the weather is warmer, making it perfect for outdoor activities and exploration.

Portland is Maine’s largest city behind Lewiston and Bangor and is known for its marine and culinary industries, along with art galleries. From wandering through the city center to enjoying the best views from the nearby lighthouses, here are the best things to include in an itinerary for a long weekend in Portland, Maine .

  **Please note that this blog post uses affiliate links meaning that if you make a purchase via my affiliate link, I receive a small commission at no additional cost to you. I only promote and talk about products and services that I have used and like. During my time in Portland in 2023, the Blind Tiger Portland hosted me.

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Traveling to Portland, Maine for a Getaway:

Between the poetic harbors and wharves, delicious lobster, picturesque lighthouses and the charming city, there’s so much to fall in love with in Portland, Maine and that’s why it makes for the best long weekend in New England.

The two times I visited Portland, Maine were during road trips. Please note that it’s around a six-hour drive from the NYC area to Portland, a two-hour drive from the Boston area and around a five-in-a-half-hour drive from Montreal. If you decide to drive to Portland and don’t want to put miles on your vehicle or don’t have a car to take with you, it’s best to rent one .

If you plan to fly into Portland , the nearest airports are Portland International Jetport or Portsmouth International Airport at Pease . You can find affordable flights through Skyscanner .

Overall, you don’t need a vehicle to get around the city of Portland, Maine, but if you plan to venture to different areas of Maine, you’ll need a rental car .

Walking everywhere downtown is easiest when getting around Portland since all the best restaurants, shops, bars, etc., are within walking distance. You can also utilize rideshare and the Greater Portland Metro , a bus service with regional transit options. There is also a ferry system in Portland, Maine, called Casco Bay Lines , where you can enjoy year-round water transportation services during your long weekend itinerary.

In addition to the city ferry, you can enjoy private cruises with a captain through Casco Bay Custom Charters and Fogg’s Water Taxi & Charters .

If you want an RV for your next trip, reserve it here !

How Many Days in Portland:

From exploring the city and enjoying Portland’s renowned seafood restaurants, coffee shops, local breweries, art galleries and beautiful surroundings, to enjoying the jaw-dropping surrounding beach towns, I suggest spending at least four days there.

During a Portland, Maine itinerary for 4 days , you must dedicate a day or two to experiencing everything the city offers and another two days to venturing out to the charming coastal towns and witnessing the most photographed lighthouses.

When planning your Portland, Maine itinerary , please consider that things are spread out in the area, ranging from 20-minute to 40-minute drives. You’ll become overwhelmed if you try to fit too many activities in one day. Plus, you’ll want to dedicate much time to each location.

Where to Stay in Portland, Maine:

Located in the West End of Portland, within a short walk to the downtown area, is the Blind Tiger by Lark Hotels . This luxury boutique hotel is the best place to stay in Portland. It’s welcoming, cozy and convenient!

There are two Blind Tiger Portland locations: one on Danforth Street , where I stayed, and one on Carleton Street , which is in the same residential area. Both properties are also in historic buildings that offer cozy living spaces, comforting rooms and modern amenities.

The Blind Tiger on the charming Danforth Street is in a 19th-century guest house and is perfect for a staycation, a girl’s trip and a romantic getaway. Booking a stay at this lovely accommodation will make you feel like a true Portlander!

Staying at Blind Tiger Portland :

Overall, the Blind Tiger Portland on Carleton Street boasts vintage furniture and items that have been collected over time and Danforth Street has unique pieces from all over the world. Only six rooms are at Blind Tiger ’s Carleton location and nine at Danforth Street.

While at Blind Tiger Portland , I stayed in the Event Records room in the 1901 John Calvin Stevens-designed wing. It features a large bay window that offers a lot of natural lighting and views of the lovely Danforth Street, a wood-burning fireplace and a sitting area. A large ensuite bathroom is also attached to the room, which includes a walk-in shower and bath amenities from Lather .

The other rooms you can choose from at Blind Tiger on Danforth Street are the Baxter , Bon Viveur , Daymark , Diavolo , Eight Bells , Evangeline , Green Eyes and Vandercook . The rooms you can stay at on Carleton Street are here .

During a stay at the Blind Tiger Portland , you can also enjoy a complimentary breakfast every morning. There’s a toast and yogurt bar where you can savor homemade bread, fresh fruit, pastries and Danishes, jams, oatmeal, fresh coffee or tea and more.

The Blind Tiger also has high-speed WiFi, open pantry access for mid-day and evening snacks, basic hotel room essentials, personalized concierge services, a Peloton studio, a billiard room in the guest house’s historic speakeasy and picnic amenities.

Staying at the Blind Tiger is a great option if you’re looking for a place to make you feel at home during a long weekend in Portland.

Long Weekend Portland, Maine Itinerary for 4 Days:

If you plan to do a Portland, Maine weekend getaway , it’s best to follow the below itinerary for 4 days:

Day 1: Explore Portland, Maine

Stroll through portland’s old port:.

The Old Port of Portland, Maine is one of the very few working waterfronts that remain in the U.S. It’s also the second largest fishing port, making it one of the best places for seafood in the world!

All travelers must include exploring the Old Port in their Portland, Maine itinerary . Portland’s Old Port is one of the most charming spots in New England and boasts cobblestone streets, historic brick buildings, a lively atmosphere during warm and sunny days and a poetic vibe during cooler, rainy days.

One of the best things to do in Old Port is stroll along Congress Street, considered Portland’s Main Street. Not only are there a lot of great restaurants, clothing boutiques, bars and souvenir stores situated along Congress Street, but it’s also a cultural center with street art to admire, small parks to relax at and museums like the Portland Museum of Art to enjoy.

Other great things to do in Old Port are to walk the piers, grab a drink and listen to live music at a microbrewery like Stars & Stripes Brewing on Spring Street, savor a lobster roll at High Roller Lobster Co. on Exchange Street or a delicious sandwich from Duck Fat on Middle Street and enjoy a sweet treat at Gorgeous Gelato on Fore Street.

Savor Warm New England Clam Chowder:

Gilbert’s Chowder House is an iconic eatery you cannot exclude from your Portland, Maine itinerary. Located off the wharf on Commercial Street, Gilbert’s Chowder House is a cozy spot to savor a heartwarming New England clam chowder and other delicious soups.

You can sit inside or enjoy the Portland waterfront outside at Gilbert’s Chowder House . This award-winning restaurant also has fresh seafood, local microbrews and more. It’s a must-visit spot near the 1862 U.S. Custom House Wharf.

Enjoy Scenic Views on the Eastern Promenade Trail:

Portland is a beautiful city and one of the best ways to enjoy its scenic views is by walking along the Eastern Promenade Trail . It’s a coastal trail built along an old rail corridor that offers views of the harbor and Casco Bay.

The Eastern Promenade Trail is an easy, flat 2.1-mile path that follows the water’s edge and leads to Portland’s East End Beach.

Not only can you get exercise by walking along the Eastern Promenade, but you can also enjoy a picnic, go swimming during the summer months, bird watch and visit the Eastern Prom Food Truck Park, where you can savor everything from Asian food to vegetarian falafel.

The Maine Narrow Gauge is a railroad and museum that takes visitors around the promenade and teaches people about Portland’s history. During the holiday season, this historic train is made into the Polar Express™ .

Sip Craft Beer at Shipyard Brewing Company :

The perfect place to sip incredible craft beer during an afternoon in Portland, Maine is Shipyard Brewing Company , in the heart of downtown.

Overall, Shipyard Brewing Company is a family-owned brewery that serves award-winning beer sold all over the United States. The most famous beers are the Summer Ale, American Pale Ale, Discovery IPA, Export Golden Ale and the Pumpkinhead Ale.

Shipyard Brewing Company is a great spot to enjoy a flight of beers and has live music and great food like pizzas, sandwiches and salads.

Have Dinner on the Wharf:

During the first evening of your Portland, Maine itinerary, it’s a must to enjoy a delicious seafood dinner at Boone’s Fish House & Oyster Room on the Custom House Wharf or DiMillo’s On the Water on DiMillo’s Marina.

Boone’s Fish House & Oyster Room is a fantastic spot to cozy up since there are several fireplaces and you can have incredible seafood comfort dishes like a Maine crab roll or a lobster mac and cheese.

For an upscale waterfront dining experience, DiMillo’s On the Water is a wonderful restaurant to savor whole Maine lobsters, and freshly caught local fish like haddock, sea scallops, tuna tartare, oysters and more.

Day 2: Admire Historic Lighthouses during a Weekend in Portland, Maine

Have a lovely brunch in downtown portland:.

A Portland, Maine vacation is incomplete without enjoying brunch. Overall, Portland has a lot of great brunch spots and one of the best is a farm-to-table gastro-pub called Little Tap House . You can get anything from breakfast bowls to omelets.

Other wonderful brunch places to add to your Portland, Maine long weekend itinerary are Becky’s Diner , Hot Suppa , Miss Portland Diner and Union at the Press Hotel .

Visit Spring Point Ledge Light in South Portland:

Situated right off the Southern Maine Community College campus, the Spring Point Ledge Light is a dangerous obstruction on the west side of the metro area, on the main shipping channel. It’s around a 15-minute drive from downtown Portland.

Unlike many of the lighthouses in Maine and New England, the Spring Point Ledge Light is built of brick instead of cast iron and is located at the end of a 900-foot breakwater. The large pieces of rock allow you to walk across the breakwater to the lighthouse easily. Plus, walking over these giant rock boulders is a lot of fun.

When you visit Spring Point Ledge Light , you can enjoy views of the harbor, historic forts and the glistening Casco Bay. I recommend wearing comfortable shoes when you walk across the breakwater because there are many ways you can fall and get hurt. Always be mindful!

See the Oldest Lighthouse at Fort Williams Park:

The oldest lighthouse in Maine, Portland Head Light , is 15 minutes south of Spring Point Ledge Light .

This picturesque lighthouse is located in the affluent town of Cape Elizabeth in Fort Williams Park.

The park features 90 acres of rugged beauty along Casco Bay. There are also several hiking paths with beautiful cliffside views of the water crashing onto the rocks. Additionally, there are many great lookout spots, a rock beach, picnic areas, a playground, ball fields and more.’

As you continue to walk south in the park, you can see the symbolic Portland Head Light , modeling its beauty on the coastal cliffs of Cape Elizabeth.

The Portland Head Light is located at the head of the primary shipping channel into Portland Harbor. Gazing out at the beautiful lighthouse reminded me why I chose to visit Maine in the first place.

Situated in Fort Williams Park is Bite Into Maine , an airstream selling some of the best lobster rolls in Portland. It’s a great place to grab lunch in the area!

Do a Casco Bay Cruise:

A long weekend getaway to Portland, Maine is incomplete without doing a cruise around Casco Bay. It’s one of the best ways to see the beauty of Maine!

Through Casco Bay Lines , you can enjoy specialty cruises (weddings, lobster bakes, corporate events, etc.), concert cruises, sunrise/sunset cruises and more. These cruises go to six islands in Casco Bay, like Peaks Island, the most famous island off Portland; Little Diamond Island; Great Diamond Island; Long Island, Chebeague Island and Cliff Island.

If you only have time to visit one island, you must explore Peaks Island! It’s a popular summer destination and home to many artists, historical sites, a charming downtown area and natural beauty.

Most people get around Peaks Island via a golf cart. Some of the top things to do are to get cinnamon buns from Peaks Café , enjoy fantastic seafood with incredible views at Island Lobster Company , go on a kayak or bike tour around the island, shop at the local boutiques, learn about the island’s history at Fifth Maine Museum and cool off to homemade ice cream from Down Front .

Savor Fresh Oysters at Eventide :

A long weekend itinerary for Portland, Maine must include having dinner and drinks at Eventide Oyster Co. in Old Port. This award-winning restaurant is swanky, cozy and offers the best oysters you’ll ever have! (There is also a location in Boston.)

During my evening at Eventide , I savored the raw oysters on a half shell from Maine and the surrounding area. Eventide is also known for its cocktails and buns/rolls. I had the Mez-Call Me Maybe cocktail, which included mezcal, tequila, house tonic and Luxardo, along with a Maine crab roll.

Day 3: Enjoy Portland’s Beaches during Your Portland, Maine Getaway

Grab breakfast at the holy donut :.

You must stop at a Holy Donut location during your weekend trip to Maine ! The Holy Donut is home to Maine’s potato donuts made from scratch daily.

There are two locations in Portland – one located downtown on Commercial Street and the other on Park Avenue. The other Holy Donut locations are in Scarborough and Arundel, Maine.

You can find various flavored treats at The Holy Donut , including seasonal flavors. The most popular are maple bacon, pomegranate, vanilla glazed and chai. It’s a great spot to grab a quick breakfast and enjoy a freshly brewed cup of Wicked Joe Organic Coffees .

Explore Two Lights State Park:

Another beautiful area of Portland to explore is Two Lights State Park in Cape Elizabeth. It’s a breathtaking rocky coast with twin lighthouses and a light station that can be seen up to 17 miles at sea.

Two Lights State Park is 41 acres and is one of Maine’s most breathtaking places. There are shoreline trails, picturesque lookouts, incredible biodiversity and a wonderful lobster shack.

The Lobster Shack at Two Lights is a gem in the Portland area and must be included in your Maine itinerary! There is indoor and outdoor seating, but you’ll want to sit outside, overlooking the ocean. You can savor Maine lobster rolls, which are chilled and made with mayo, along with crab rolls, clam cakes, whole lobsters, freshly caught fish and more.

Overall, this lobster shack is one of the best places to have lunch during a trip to Portland, but please note that when you visit on a beautiful day, there will be a line to order food. Waiting in line is worth it because the food and atmosphere are incredible! It’s one of my favorite spots in New England!

Walk around Old Orchard Beach and Biddeford Pool:

A 4-day weekend itinerary for Portland, Maine must have you visiting the local beach towns. Two wonderful locations to enjoy a scenic drive to are Old Orchard Beach and Biddeford Pool.

If you skip breakfast downtown and don’t visit Two Lights State Park, I suggest heading to Old Orchard Beach in the morning and starting your day at Joseph’s by the Sea . This beach town is a 25-minute drive from the city.

Known as Maine’s premier beach resort, Old Orchard Beach has something for everyone, whether strolling along Old Orchard Pier, relaxing at the beach on a warm day, going mini golf, biking the Eastern Trail and more.

Another 20 minutes south of Old Orchard Beach is Biddeford Pool, a large tidal pool off Saco Bay. It’s a peaceful location with a 1.5-mile historic walking trail at East Point Audubon Sanctuary .

At the sanctuary in Biddeford Pool is the haunting Wood Island Lighthouse , a picturesque rocky shoreline where you can see a variety of bird species. It’s also a lovely spot to have a picnic!

In addition to conquering the trail, you must also visit the Fortunes Rocks Beach on a warm and sunny day, go paddle boarding, watch a performance at City Theater , visit Banded Brewing or Round Turn Distilling , and see a movie at the Saco Drive-in .

Stroll through the Charming Kennebunkport:

Located another 15 minutes south of Biddeford and over 35 minutes from downtown Portland is the charming coastal town of Kennebunkport. It is one of Maine’s most popular vacation destinations, making for a wonderful day trip from Portland.

Kennebunkport is one of the oldest European-settled towns in the USA and offers a charming downtown area to wander through, shop, eat and make memories.

Other great things to do in Kennebunkport, Maine are to go whale watching , relax at Gooch’s Beach on a warm day, learn about the U.S. Presidents that have vacationed in this town at the First Families Kennebunkport Museum , hike the 2-mile Parson’s Way, see the Wedding Cake House and go antiquing.

The best restaurants in Kennebunkport are Alisson’s Restaurant & Pub , White Barn Inn Restaurant , The Clam Shack , Nunan’s Lobster Hutt and Rococo Artisan Ice Cream .

Enjoy Dinner in Old Port:

If you return to Old Port for dinner, an excellent restaurant to eat at is Central Provisions on Fore Street. It features incredible small plates, craft cocktails and a great atmosphere.

Afterward, head to Three Dollar Deweys on Commercial Street for live music and a good time!

Day 4: Conclude Your Portland, Maine Vacation

On the last day of your Portland, Maine itinerary, you could extend your trip and head north to Bangor, adventure through Acadia National Park and Bar Harbor or head south to Portsmouth or Boston .

Explore Portsmouth, New Hampshire:

Since I was heading south, I chose to make a pit stop on my road trip in Portsmouth, New Hampshire.

Located a little less than an hour south of Portland, Portsmouth is a charming port city along the Piscataqua River. It features colorful Colonial buildings, a quaint downtown area, an iconic church, excellent coffee shops, restaurants, breweries and stores.

During your time in Portsmouth, you must learn about Portsmouth’s history by visiting the Strawberry Banke Museum .

You must also see the iconic North Church , enjoy a drink and good read at Portsmouth Book & Bar , savor delicious pizza at Flatbread Company , shop through the local boutiques, admire breathtaking views from the Portsmouth Harbor Lighthouse , stroll along the scenic Portsmouth Harbor Trail , taste local craft beer at Portsmouth Brewery and treat yourself to something delicious at Fezziwig’s Food & Fountain .

Love this article? Then, you’ll enjoy the below:

Fall Vacations on the East Coast

Girl’s Trip on Martha’s Vineyard

Visiting Salem in October

I hope you all enjoyed discovering the best things to do during a 4-day long weekend itinerary for Portland, Maine. If you have any questions, please email me at [email protected].

Make sure to pin this post if you find it useful!

Basic Facts of the United States:

Currency: United States Dollar, Capital: Washington D.C., ME State Capital: Augusta, Time Zone: Eastern Standard Time

*Anything could happen during your travels. Always make sure you are insured in case there are unforeseen circumstances such as lost luggage/theft, natural disasters, personal liabilities and more.  Click here  to get insured for your next trip.

Shop my Portland, Maine Look:

Click here  to shop my  Poshmark  closet!

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28 comments.

This is my husbands DREAM vacation!! We are hoping to get there ASAP lol!

Portland is so beautiful, you guys would love it so much! If you have the time too, I recommend visiting Acadia National Park too.:)

It sounds like a wonderful way how to spend a long weekend ♥! And Donuts for breakfast – seriously?? That must be soo amazing :D!!!

Yes, it was quite lovely and Maine is so peaceful! lol yes, I need to do better about not having donuts for breakfast, but they are amazing! 🙂

Didn’t realize there is a Portland in Maine! Gorgeous picture Taylor. Makes me want to visit this place!

Yes, it’s so beautiful and the seafood is amazing! You definitely have to go at some point.

I’m wondering where you saw that pretty white building? Which beach and how did you get there? Thank you!

Hi Amanada, If you’re referring to the white hotel on the beach, that was in Biddeford Pool, Maine. Overall, Biddeford isn’t a big town and it’s very quiet. You could easily walk around the beach and find it, that is what we did. We mainly walked around the East Point Sanctuary. Honestly, I don’t know the name of the hotel and I even tried looking it up and couldn’t find it. I visited in 2017, so it possibly may not even be there anymore. I couldn’t tell if it was abandoned when I was there.

Such a beautiful area of the USA. I haven’t been to this part yet, but it looks so beautiful. The food also looks delicious.

New England truly is beautiful and I love all of the seafood there. 🙂

Wow such an amazing post on Portland, Maine. The scenic beaches and landscape is tempting and so is the seafood! Makes me want to visit it!

Thank you so much Puloma! It really is such a beautiful part of the country. 🙂

Maine is just so beautiful in the photos. I would love to know more about campgrounds in the state.

It really is such a beautiful state. I don’t know much about camping there, but I can imagine it is wonderful! 🙂

I loved Portland and especially Vena’s Fizz House! Looks like you had perfect weather too.

Yes, it is such a cute spot! I’d love to go back. I went during Memorial Day Weekend in 2017 and it was quite chilly, but we were lucky with no rain. 🙂

Looks like you did all the quintessential things when visiting Maine! I pinned this post as I’ve always wanted to visit the state. Oh, those lobster rolls and a bowl of clam chowder are calling my name.

The seafood there is some of the best in the world! You would love Portland Vanessa. 🙂

We spent a week on the coast but only got a few hours in Portland. But we did find some great seafood for lunch one day! I can see that next time we need to spend some more time there. A great base to see the lighthouses along the bay.

Yes, it is such a nice city! I loved all the seafood there. 🙂

I love Portland! One of my best friends live there but I haven’t been in years. Your trip and photos look so fun!

It is such a great city! 🙂 Thank you!

Wonderful itinerary! You clearly enjoyed Portland, ME. As you note Airbnb is a great option for short or long stays. If you are travelling during the peak summer season, and you have your eye on a particular spot, I would encourage making restaurant reservations well in advance.

@Taylor, If you make the trek back to coastal Maine, we’d love to host you and have you review our vacation cottage. https://airbnb.com/h/buoysonbates

Thank you so much Dan! I’d love to revisit Maine and stay at your vacation cottage. Please email me at [email protected] .

We recently stumbled across your Portland, Maine, article and enjoyed reading it. There is certainly no shortage of things for visitors and locals alike to explore. I must add that there are many “Best Tattoo Parlors and Artists in Maine” , which will be another memorable experience while visiting here.

Thank you so much and yes, a lot of people love getting tattoos on trips to remember their experience! 🙂

Such an amazing post on Portland, Maine..!!!! I loved the fact that you mentioned every quintessential thing to keep in mind while visiting the place. The photos of Old Orchard Beach and Biddeford Pool are tempting me to visit them ASAP!

Thank you so much! It’s absolutely beautiful in Maine. I am hoping to revisit this upcoming fall.

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7 Day Maine Coast Road Trip Itinerary: Where to Go and What to Do

Seven days for a Maine coast road trip is the perfect amount of time to see some great cities and immerse yourself in the wonderful local culture of coastal Maine.

From charming small towns that are not-to-miss (and for reasons we explain, below) to bigger cities that will round out the trip, you're sure to have fun in this stunning New England state.

Disclosure: There are affiliate links in this post, which means we may earn a small commission if you click the link and proceed with a purchase, at no cost to you . We truly only recommend hotels, products, and services we personally use. As Amazon Associates, we earn from qualifying purchases. We were hosted by Visit Maine. All opinions are our own.

Maine Coast Road Trip Overview

We flew into Maine's airport in Portland from RDU airport in Raleigh to start our trip. Another easy airport to get to is Boston Logan International Airport, which is just a two-hour drive from Portland.

We rented a car to road trip north from that point. You can begin in Portland and do the reverse of our trip. It depends on your preference. However, we chose to go to the furthest point north of our trip and then drive back south so when we ended and needed to fly home, we were just minutes from the airport.

• Days 1 to 3: Bar Harbor
• 3 to 5: Boothbay Harbor
• 5 to 7: Portland

If you want to extend your time in Maine, we recommend a Maine Windjammer cruise . This will give you a completely unique view of the coast. We had a fantastic experience sailing Maine's coast this way for four days as an add-on to our road trip.

Days 1 to 3: Bar Harbor, in Northern Maine

Bar Harbor was so beautiful. If you like a bustling and walkable small town on the water, you'll love it here. Especially because you can do excursions like a lobster boat tour and go whale watching.

We stayed at the most amazing modern bed and breakfast called The Atlantean . The owners blew us away with their hospitality and cooking. (The breakfasts there were the best meals we had of our entire road trip along with Maine foods like lobster and blueberry donuts!)

One of the best things to do here was to simply take walks and stop for ice cream or coffee, and sit in the park to enjoy the view of the water. Another absolutely fantastic view was from the top of Cadillac mountain. It was special to see the water and its many islands like birds in the sky from that vantage point.

Acadia National Park is one of the main reasons many people add Bar Harbor to a Maine coast road trip itinerary. Truthfully though, the town alone is worth the visit.

That being said, Acadia National Park is refreshing and attractive. We enjoyed an easy hike there one afternoon around Jordan Pond and drove the loop road the next day to see some more of Maine's coast. (Jordan Pond is on the list of things to do in the park on the super helpful National Park Planner. If you plan on going to even two National Parks in the near future, you need this !)

If you're going to Acadia National Park during summer , we highly recommend getting a Bug Bite Thing to combat bug bites while you're there. We took a very leisurely short walk in the park at some pretty gardens they have and man oh man….I got eaten alive by the bugs! We are so grateful for this device that eliminates the itch in seconds.

Must-have item for your Tropical vacation:

The only thing we have tried that gets rid of bug bites from your skin is The Bug Bite Thing . This item is a MUST pack when we travel. We always pack one in our backpack/day bag and another in our luggage. Don't travel without it! And yes, it really works !

Days 3 to 5: Boothbay Harbor

One of the nice things about Boothbay Harbor was how it felt less busy than other areas we visited, and there were a bunch of charming hotel options. There was less to do there than in Bar Harbor and Portland. This meant we could relax a little more and sleep a little later when we were there during our vacation.

It was worth a stop for its Botanical Gardens alone. Secondly, we loved that there was a little local brewery and, thirdly, how walkable the town was. A simple pleasure in life is walking around a town during a Maine coast road trip on a beautiful New England summer day.

Days 5 to 7: Portland

Portland impressed us with its mix of old and new. It's very much a functioning port city – as it has been for well over a century – and the tourist scene was thriving.

This size city really speaks to the energized explorer in us that gravitates toward liking urban environments that aren't too big and aren't too small. (It's one of the reasons we chose Raleigh, NC , as our home city.)

There were great restaurant options where we could have local seafood, tours that helped us get familiarized with the city streets, a posh Marriott hotel we enjoyed, and boat tours where we could navigate the water on with an expert guide.

There were colorful murals, lighthouses, and waterfront views…what more could you ask for?

Sea Bags flagship store is also there and it was fun to learn about the bags made from recycled sails .

5 Day itinerary for Maine's Coast

If you only have 5 days, we would recommend the following abridged version of what we did:

• Days 3 to 5: Portland

If you have to skip a city, skip Boothbay Harbor. You can even stop at the Botanical Garden in Boothbay Harbor on your way to Portland from Bar Harbor, but simply continue your drive after you visit the gardens instead of staying overnight.

Extending Your Vacation for a Maine Windjammer Cruise

We feel so fortunate to have experienced Maine's beautiful coast by sea and by land. Taking a schooner boat, an overnight Maine sailing trip with Maine Windjammer Association aboard American Eagle, was really outstanding.

It's unlike any “typical” cruise you may think of. If you're used to sailing or have gone on a sailboat you can stay on overnight, it's very much like that.

Our seven-day Maine coast road trip started after the sailing and it was the perfect complement to the sea portion of our summer Maine vacation.

Read this next:

• Planning your Trip to Maine in the Summer: 20 Things to Know
• Food Maine is Known For (Lobster and Beyond)
• Best Bed and Breakfast in Bar Harbor: Atlantean Cottage (Our Favorite Accommodations in Maine)

I want to go to Maine after I have retired. My favorite food is seafood – shrimp, crab legs, and lobster. I would like to do a lobster bake in Maine! Thank you for this information.

Need a lot of advice from Kentucky to there. Thank you

Hi Bonnie – it would be best if you flew from Kentucky to Maine, then rented a car to do a road trip of the coast. Follow our road trip plan for the perfect 7 days!

So glad this inspired you, Bonnie!

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The Ultimate 5-Day Maine Itinerary: Unforgettable Adventures Await

Maine is a beautiful state located in the northeastern region of the United States. Known for its stunning coastline, delicious seafood, and charming small towns, Maine is a popular destination for travelers from all over the world.

If you’re planning a trip to Maine and want to make the most of your time there, this 5-day itinerary is for you.

Table of Contents

5-Day Maine Itinerary

Day 1: portland.

Portland is Maine’s largest city and a great place to start your trip. Spend the morning exploring the Old Port, a historic district filled with cobblestone streets, boutique shops, and delicious restaurants.

Be sure to stop by the Portland Head Light, one of Maine’s most iconic lighthouses, for some stunning views of the Atlantic Ocean.

In the afternoon, head to the Eastern Promenade, a beautiful park overlooking Casco Bay. Take a walk along the waterfront trail or have a picnic on the grassy hill.

For dinner, try Eventide Oyster Co., a popular seafood restaurant known for its delicious lobster rolls and raw oysters.

Day 2: Acadia National Park

Acadia National Park is one of Maine’s most popular attractions and a must-visit for any nature lover. Start your day early and drive to the park, which is located about 3 hours from Portland.

Spend the day hiking, biking, or kayaking in the park’s stunning natural beauty. Be sure to visit Cadillac Mountain, the highest point on the East Coast, for some breathtaking views of the surrounding landscape.

For dinner, head to Bar Harbor, a charming coastal town located just outside the park. Try the lobster bisque at Stewman’s Lobster Pound or the blueberry pie at Jordan Pond House.

Day 3: Camden

Camden is a picturesque town located on the coast of Maine.

Spend the morning exploring the town’s charming streets and visiting the local shops and galleries. Be sure to take a walk along the harbor and watch the boats come in and out.

In the afternoon, head to Camden Hills State Park, where you can hike to the top of Mount Battie for some stunning views of the surrounding area.

For dinner, try Long Grain, a popular Thai restaurant known for its delicious food and cozy atmosphere.

Day 4: Kennebunkport

Kennebunkport is a quaint coastal town located about 2 hours from Camden.

In the afternoon, head to Goose Rocks Beach, a beautiful stretch of sand and surf located just outside of town.

For dinner, try The Clam Shack, a popular seafood restaurant known for its delicious lobster rolls and fried clams.

Day 5: Freeport

Freeport is a small town located about 30 minutes from Portland. Spend the morning shopping at the town’s famous outlet stores, which include brands like L.L. Bean, Patagonia, and Nike.

In the afternoon, head to Wolfe’s Neck Woods State Park, where you can hike through the forest and along the coast. For dinner, try the lobster mac and cheese at Linda Bean’s Maine Kitchen.

What to Prepare

Before embarking on your trip to Maine, there are a few things you should prepare.

• First, be sure to pack appropriate clothing for the season. Maine can be quite chilly, even in the summer, so be sure to bring layers and a warm jacket.
• Second, make sure you have a good pair of hiking shoes if you plan on doing any outdoor activities.
• Finally, be sure to bring a camera to capture all of the stunning scenery and memories from your trip.

Maine is a beautiful state with so much to offer. Whether you’re a nature lover, a foodie, or just looking for a relaxing getaway, Maine has something for everyone. This 5-day itinerary is just a starting point – there are so many other amazing places to explore in Maine.

So pack your bags, hit the road, and get ready for an unforgettable adventure in the Pine Tree State.

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23 Incredible Road Trips in the U.S.

Whether you’re looking for sweeping views of the pacific ocean or a multiday adventure through national parks, these road trips provide plenty of opportunities to explore the united states..

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Glacier National Park is one of many scenic places you can visit on an American road trip.

Photo by Zack Frank / Shutterstock

In a country as large as the United States, there’s no shortage of destinations and detours to explore by car . Whether your idea of the perfect American road trip entails an epic, cross-country journey or a shorter jaunt through a few of its most iconic national parks , your options are as large and varied as the country itself.

Even if you don’t have the time to drive cross-country, there are plenty of road trip routes (ranging from three days to a week or longer): classic California itineraries , New England routes that shine especially well in the fall, scenic East Coast adventures, and a variety of Midwest journeys for folks farther from the coasts.

No matter your mode of transportation—be it van, RV, motorcycle, or four-door sedan—these are 21 of the best road trips in the nation to consider.

Plan your next Route 66 trip around thirst-quenching stops.

Photo by Peek Creative Collective/Shutterstock

There are many ways to do a cross-country road trip in the USA, but these two itineraries will take you through some truly iconic American places.

1. Chicago to Los Angeles: A Whiskey Road Trip on Route 66

It doesn’t get more American than a 2,000-mile drive along the entirety of Route 66. There are endless ways to take this legendary trip (including an EV version —but to take your cross-country road trip to the next level, we recommend exploring another American pastime: whiskey.

Starting in Chicago and ending in L.A., you’ll stop by some of the leading craft distilleries in the United States, like Few Spirits in Chicago, Still 630 in St. Louis, and Red Fork Distillery in Tulsa. In between tastings, make time for detours to natural attractions, like the Grand Canyon, and quirky roadside curiosities, like Cadillac Ranch in Amarillo, Texas. Just remember to drink responsibly—this is a road trip after all.

Plan your trip

The full itinerary: Put a New Twist on Route 66—Make It an American Whiskey Road Trip

No cars are allowed on Mackinac Island, so you need to park before taking the ferry to this spot.

Photo from Shutterstock

2. Bangor, Maine, to Seattle, Washington: The Great Northern on U.S. Route 2

Covering both the U.S. and Canada, a cross-country trip along U.S. 2 is ideal for anyone who wants to experience the vast diversity and expansiveness of North America. This drive runs the entire top border of the U.S. and showcases otherworldly natural wonders like Acadia National Park in Maine, the Apostle Islands National Lakeshore in Wisconsin, and Mackinac Island in Michigan. The route also passes through Canada, taking road-trippers through Ontario into Quebec—this route may focus on nature, but you won’t want to miss a stop in Montreal or Ottawa.

You’ll also get to explore Montana and Glacier National Park ( reservations may be required ) before passing the Columbia Plateau and ending in the Pacific Northwest’s largest city, Seattle. Don’t miss spending time in the Olympic Peninsula (home to Olympic National Park) for a peek at one of the most scenic places on the West Coast.

3. Dana Point to San Francisco: Driving California’s Pacific Coast Highway

The seemingly endless views of the Pacific Ocean along Highway 1 (also known as the Pacific Coast Highway) are what road trip dreams are made of, and exactly what makes this California road trip so popular. However, with so many stops along the 655-mile stretch, we pulled together a list of the ones well worth pulling over to view. Don’t miss the perfect surfing waves in Santa Cruz, seasonal cuisine in Malibu, an afternoon a the boardwalk in Santa Monica, or a night in Big Sur as you drive between Dana Point (just south of Los Angeles) and San Francisco.

• The full itinerary: The Best Stops for a Road Trip on the Pacific Coast Highway
• The AFAR Guide to San Francisco

The seaside town of Monterey was the setting for John Steinbeck’s Cannery Row .

Photo by Denise Lett/Shutterstock

4. Big Sur to Mono County: A Literary Road Trip Through Northern California

Yes, this itinerary requires you actually put down your book to drive, but seeing some of the pivotal places that shaped American authors will be so worth it. Follow in the footsteps of writers like Jack Kerouac, Maya Angelou, and Amy Tan on this road trip that takes you through literary landmarks in Northern California, such as Caffe Trieste, a meeting place for Jack Kerouac, Allen Ginsberg, Alan Watts, and other bohemian writers and thinkers. This 12-stop itinerary is perfect if you live in the San Francisco Bay Area because you’ll be able to stay make these trips in one or two days.

The full itinerary: The California Road Trip All Book Lovers Should Take

Arizona may take its nickname from the Grand Canyon, but the state has far more natural wonders than just that one.

Courtesy of Shutterstock

5. Phoenix to the Grand Canyon: An Iconic Arizona Road Trip

This 240-mile Arizona road trip takes travelers along some of the state’s most iconic highlights, including its most famous one, the Grand Canyon. A great itinerary for first-time visitors and returning travelers alike, it offers plenty of opportunities for scenic drives, hiking, and biking—as well as tasty food along the way. Hike the 2,704-foot-tall Camelback Mountain in Scottsdale or take in the beautiful red rocks of Sedona on a hike to Cathedral Rock while exploring the Grand Canyon State.

• The full itinerary: The Classic 5-Day Arizona Road Trip
• Grand Canyon guide: The First-Timer’s Guide to the Grand Canyon
• Where to eat in Phoenix: A Chef’s Guide to the Best Restaurants
• Where to stay: The Best Hotels in Arizona ; The Best Airbnbs in Sedona

The Delicate Arch living up to its name in Utah’s Arches National Park

Photo by tusharkoley / Shutterstock

6. Zion to Grand Canyon: A National Parks Road Trip in the Southwest

If you’re looking to visit as many national parks as possible in one road trip, this southwestern itinerary is for you. This journey through Utah and Arizona lets you hike Angel’s Landing in Zion, feel tiny under Delicate Arch in Arches National Park, explore Fairyland Loop Trail in Bryce Canyon, and, of course, raft down the Colorado River in the Grand Canyon. Most visitors to the Grand Canyon remain on the rim, but take at least four days to venture within the canyon and take advantage of the trails and river rafting.

• The full itinerary: The Ideal Road Trip Through U.S. National Parks
• Utah’s 8 Best National Parks and Monuments
• 10 Best National Parks and Monuments in Arizona
• The First-Timer’s Guide to the Grand Canyon

Stop and admire the winding roads of the San Juan Skyway.

Photo by Anh Luu/Shutterstock

7. San Juan Scenic Skyway Road Trip: An Adventure Through Southwestern Colorado

This Colorado trip takes you along the 232-mile loop of the San Juan Scenic Skyway, where you will see plenty of alpine forests, mining towns, and craggy peaks. And for anyone looking to enjoy refreshments after a long day of driving, this route features many opportunities to stop at some of the best breweries in Colorado , such as Ska Brewing Co. in Durango.

• The full itinerary: The Ultimate Southwestern Colorado Road Trip
• Five Classic Colorado Road Trips To Take This Year

In small-town Buena Vista, the riverfront Surf Hotel offers front-row seats to Colorado-style adventure seekers.

Courtesy of the Surf Hotel

8. Denver to Montrose: A 420-Mile Road Trip Through Colorado

Want to explore even more of the Centennial State? Head out on this weeklong road trip where you can fish for salmon in Colorado’s largest reservoir, visit numerous small towns, like Paonia and Crawford, with thriving art scenes along the Colorado Creative Corridor , and explore Black Canyon of the Gunnison National Park, one of the least visited national parks in the nation.

• The full itinerary: Art Stars, High-Altitude Wines, and a Remote National Park: The Ultimate Colorado Road Trip
• Where to stay: The Best Hotels in Colorado
• The AFAR Guide to Denver

Portland may be Oregon’s largest city, but with a population of some 652,000 (or 2.5 million in the larger metropolitan area), it isn’t intimidatingly large.

Photo courtesy of Travel Portland

9. Portland to Astoria: An Oregon Coast Road Trip for Outdoor Lovers

If you love the outdoors, then this six-day road trip along the coast of Oregon is for you. After driving to Coos Bay from Portland, travelers will meander along Oregon’s dramatic, rocky coastline, discovering some quintessentially Pacific Northwest vistas along the way: evergreen forests, seaside dunes, and marine ecosystems. Between stops, there are ample opportunities to stretch your legs hiking, kayaking, or strolling around the region’s small towns—like the historic old town in Florence.

Of course, it wouldn’t be an Oregon road trip without a stop (or three) at a craft brewery, such as Fort George Brewery in Astoria, or cozy coffee shop, like Bread & Roses in Yachats.

• The full itinerary: An Outdoor Lover’s Road Trip on the Oregon Coast
• The AFAR Guide to Portland

The State Capitol Building in Nashville marks the end of this road (trip).

Photo by photo.ua / Shutterstock

10. Seneca Falls, New York, to Nashville, Tennessee: Follow the Path of the Women’s Suffrage Movement

Starting in New York’s Finger Lakes region and ending at the State Capitol Building in Nashville, this road trip traces the route of the national women’s suffrage movement. Highlights include stops at the Susan B. Anthony Museum & House ; Union Square in New York City, which was the site of the first suffrage march; and the Belmont-Paul Women’s Equality National Monument in Washington, D.C.

• The full itinerary: Celebrate Women’s Suffrage on an Epic, Self-Guided Road Trip
• Where to stay: The Best Hotels in Nashville
• The AFAR Guide to Nashville
• The AFAR Guide to Washington, D.C.

Asheville is one must-stop on a North Carolina road trip.

Courtesy of ExploreAsheville.com

11. Charlottesville to Asheville: A Scenic Road Trip Through Virginia and North Carolina

The Blue Ridge Parkway is one of the most scenic drives in the country. Beginning in the soft hilly meadows of the Appalachian Mountains from Shenandoah National Park down into the Blue Ridge Mountains, then into the Great Smoky Mountains, this five-day road trip is best done at a slower pace, which is perfect for admiring the dramatic outlooks and green plateaus. This eclectic itinerary features stops at an art museum, a dairy farm, and plenty of hiking trails.

• The full itinerary: The Ultimate Blue Ridge Parkway Road Trip
• Where to stay: 12 Dreamy Blue Ridge Mountain Cabins You Can Rent on Airbnb and Vrbo
• 8 U.S. National Park Road Trips to Take in Your Lifetime

Dowa:kwe dance group from Zuni Pueblo in 2019

Courtesy of Indian Pueblo Cultural Center

12. Albuquerque to Las Cruces: Discover New Mexico on This Three-Day Road Trip

This route steers you away from New Mexican tourist hot spots like Taos and Santa Fe and instead takes you on a three-day adventure with places that teach you about Pueblo history. You’ll stop at Indian Pueblo Kitchen (formerly known as Pueblo Harvest), a restaurant inside the Indian Pueblo Cultural Center that features Indigenous cuisine ; pick up peppers at Three Brothers in Hatch; and slide down the dunes in White Sands National Park.

• The full itinerary: This New Mexico Road Trip Is the Perfect Introduction to the Land of Enchantment

Historic Fort Martin Scott is one of the places travelers can visit to learn about Fredericksburg’s history.

Photo by Mark König/Unsplash

13. A Five-Day Scenic Road Trip Through Texas Hill Country

This Texas road trip starts and ends in San Antonio with stops in small towns like Bandera, Boerne, and consider a stop in Fredericksburg, which is one of AFAR’s best places to go in 2024 ). Over five days, you’ll find opportunities to stroll in a Japanese tea garden in San Antonio, relax along the Sabinal and Frio Rivers by inner tube, and eat as many tacos as you want. Seriously: You could eat tacos for every meal on this road trip and not get tired of them.

• The full itinerary: Tree Houses, Tubing, and Tacos: The Ultimate Texas Hill Country Road Trip

Mount McKinley looms large on a drive through Denali National Park.

Photo by warnsweet / Shutterstock

14. A Weeklong Road Trip Through Alaska’s Most Majestic Sights

This weeklong drive in Alaska starts and ends in Anchorage. You travel along four scenic byways; explore Wrangell–St. Elias wilderness, the largest U.S. national park; catch sight of Denali, the tallest peak in North America; and enjoy the surprisingly stellar food scene of McCarthy, a one-road town with only a couple dozen residents.

• The full itinerary: Glaciers, Mountain Peaks, and Organic Farms: The Ultimate Alaska Road Trip
• Which Alaska National Parks Should You Visit?

More than geothermal pools, Kirkham Hot Springs features a piping-hot waterfall.

Courtesy of Idaho Tourism

15. Boise to Sun Valley: Explore Idaho’s Scenic Byways

Even a short road trip can be packed with adventure, good food, and scenery, which is exactly what this trip from Boise to Sun Valley along Idaho’s Ponderosa Pine Scenic Byway offers. Although the drive only takes six hours, we recommend taking a few days to explore all the stops and detours along the way. One can’t-miss spot is the Kirkham Hot Springs , where you can stand under a waterfall that will splash you with 135-degree mineral water year-round.

• The full itinerary: The Little-Known Idaho Road Trip You Need to Drive
• Things to do: The Best Outdoorsy Things to Do in Idaho

Grand Portage State Park is the only state park jointly managed by a state and a Native American band.

Photo by Shutterstock/QZ

16. Duluth to Grand Portage State Park: A Scenic Minnesota Sampler

Although there are many appealing road trips throughout the Midwest, this 143-mile, three-hour circuit, which starts and ends in Duluth, Minnesota, is worth keeping in mind. Meandering north on MN-61 with this itinerary, you will enjoy prime views of Lake Superior and towns like Grand Marais, as well as Grand Portage State Park, home to waterfalls, hiking trails, and opportunities to learn about the Ojibwe community who occupy the land today. Once back in Duluth, enjoy a beer at Canal Park Brewing Company before checking into the waterfront Canal Park Lodge nearby.

• The AFAR Guide to Minnesota

Wind your way through colorful foliage in New Hampshire.

Photo by Shutterstock

17. Kancamagus Highway: A Quintessential New England Drive

Yes, you can take a road trip in New England at any time of the year , but this region shows off its best colors in the fall, when locals and tourists alike head out into the country to view the changing colors of the trees. Join other admirers of fall foliage on this popular, 34.5-mile road trip along New Hampshire’s Kancamagus Highway, colloquially known as the “Kanc,” for picturesque ponds, hiking trails, and scenic overlooks.

• Plan Your Fall Getaway With This Peak Foliage Prediction Map

Ogunquit is home to the small, postcard-perfect harbor of Perkins Cove.

Photo courtesy of QualityHD / Shutterstock

18. Maine’s “Lobster Trail”: Travel Route 1 Along the Coast

Traveling Route 1, affectionately known as “the lobster trail,” along Maine’s jagged coastline is an exercise in indulgence. Sample lobster dishes in all forms—buttered, steamed, on a roll, or even in a decadent mac-and-cheese.

The trip starts in the quaint small town of Ogunquit , with its rare (for the area) 3.5 miles of white-sand beach. Make your first lobster of the journey count, steamed with a side of drawn butter at Barnacle Billy’s in picturesque Perkins Cove harbor. Stop at Big Daddy’s for a cone on your way to the shipbuilding center—and summer home of George H. W. Bush—Kennebunkport. Stay at the recently redesigned 150-year-old classic White Barn Inn , and consider a sailing trip for an afternoon. With lobsters cooked in ocean water, the legendary lobster roll at the Clam Shack is a must.

• 8 Scenic East Coast Road Trips to Take This Year

Throughout North Carolina’s Piedmont region, innovative restaurants, shops, and restaurants like Leah & Louise in Charlotte, above, are creating a buzz.

Photo by Peter Taylor Photography

19. Raleigh to Charlotte: A 4-Day Trip Through North Carolina’s Reinvented Core

North Carolina’s Piedmont region extends from the coastal plain to the Blue Ridge Mountains, and includes farmland and rolling wooded hills, especially on the 1-40 stretch near Hillsborough. Starting in Raleigh, drive the short distances to Greensboro, Winston-Salem, and Charlotte to see how these cities are innovating through art, food, and a celebration of the past. Take your time—four days should do—to experience downtown arts districts, James Beard Award–winning restaurants, and civil rights museums that speak truths. Plan your trip

• A Road Trip Through North Carolina’s Reinvented Core

Scenic South Walton is part of the Emerald Coast of Florida.

20. Scenic Highway 30A: A Sunday Drive Through South Walton, Florida

Florida is full of places to cruise with the top down, but it’s hard to beat a Sunday (or any day) drive along Scenic Highway 30A through northwest Florida, home to a postcard-perfect stretch of seaside towns known as South Walton.

The roughly 28-mile route through South Walton County kisses the coast for nearly all its length, taking you through gorgeous residential Gulf-front communities like Rosemary Beach, Grayton Beach, and Blue Mountain Beach . Roll down the windows and let the emerald-hued views in.

Pull over to explore, too—maybe to admire the New Urbanism architecture in Alys Beach or to swim in the clear waters at Grayton Beach State Park . (The beach here has been lauded among the best in the world.)

• The full itinerary: The Florida Road Trip You’ve Been Missing

Stand-up paddleboarding is just one way to enjoy a Florida Keys sunset.

Shutterstock

21. The Florida Keys: An Island-Hopping Getaway

For a sunny road trip itinerary in Florida, skip Miami and head farther south. Beginning in Key Largo and ending in Key West, the Florida Keys Scenic Highway is often overlooked for more well-known routes up north, but it is well worth going out of your way to experience.

As the name suggests, this route is very scenic, so plan to spend at least a few days exploring it and numerous stops along the way. Some highlights include driving across the impressive Overseas Highway, stopping to admire art in the town of Islamorada, and enjoying the historic sites, food, and (of course) beaches in the city of Key West.

• The full itinerary: How to Road Trip in the Lesser-Known Florida Keys

Sun Studio in Memphis was the site of the famous Million Dollar recording session that brought together Elvis Presley, Jerry Lee Lewis, Carl Perkins, and Johnny Cash.

Photo by f11photo on Shutterstock

22. Memphis to Bristol, Tennessee: A Music-Driven Adventure

If you have about a week to spare and a deep appreciation for music, take a road trip from one side of Tennessee to the other, starting in Memphis and ending in Bristol. The eastbound trip spans genres, including rock ( Graceland ), blues ( Beale Street) and, of course, country (did you really go to Tennessee if you didn’t go to Dollywood ?). Nashville serves as the halfway point on your journey—so consider penciling in an extra 48 hours to fully explore the state capital’s greatest hits.

• The full itinerary: 5 Great American Road Trips For Music Fans

The stunning coastline near Cueva del Indio has been the backdrop of star-studded films.

Photo by Alexsf.gr/Shutterstock

23. Arecibo to Condado, Puerto Rico: A Lesser-Known Side of a Well-Loved Island

In the minds of many, trips to Puerto Rico bring images of stunning beaches , delicious foods , and maybe a bioluminescent bay or two . But there’s plenty of history to be found here, too, as Puerto Rico was home to an Indigenous population known as the Taino, a heritage many Puerto Ricans embrace. That history can be explored via a road trip. Starting in the northern town of Arecibo, travel south to Ponce, then back north to Condado—along the way you’ll encounter petroglyphs, Indigenous sites, and breathtaking natural spots.

• The full itinerary: A Puerto Rico Road Trip That Puts Indigenous Culture First

Additional road trip planning resources Picking the route for your road trip is only one part of your planning. From what snacks to pack to which podcasts to listen to, these additional resources will help you prepare for your next adventure:

• Best road trip snacks
• Road trip planning apps
• Podcasts and audiobooks to download
• What to pack for a road trip

This article originally appeared online in August 2020. It was most recently updated on April 4, 2024, to include current information. Additional reporting by Jessie Beck, Erika Owen, Ray Rogers, Terry Ward, and Sheryl Nance-Nash.

10-Day New England Road Trip Itinerary

• New England offers a variety of destinations for a memorable road trip, including Boston, Cape Cod, Providence, and more.
• Boston, Massachusetts, is one of the best New England road trip stops, known for its historical landmarks and museums, although it can be pricey and congested.
• Bar Harbor, Maine, is a must-visit when road-tripping New England in 10 days; it's perfect for nature enthusiasts, as it's home to Acadia National Park, while Portland, Maine, is a charming waterfront city with a blend of history and innovation.

The moniker of New England brings a great deal of curiosity to those looking for a new area of the world to explore. As a collection of states spanning Maine, Connecticut, Massachusetts, Vermont, Rhode Island, and New Hampshire, ample opportunities exist to take in all the area has to offer through an old-fashioned road trip.

Deciding on a route that will accommodate the top destinations New England has to offer is half the battle. The 10-day road trip below combines heritage, entertainment, and cultural opportunities to ensure a well-rounded and memorable vacation. All that's left to do is to buckle up and enjoy the adventure yet to come!

Related: These Are The 14 Most Beautiful Places To Live In New England

Boston, Massachusetts

Boston has exceptional museums, restaurants, and landmarks to visit on a road trip.

Boston is the start for those looking to road trip New England in 10 days; it's one of the oldest cities in the United States and bears much historical significance. Founded in 1630 by John Winthrop , the area was brought forward by Puritans settling in the new country of America.

Today, the capital of Massachusetts is known for its European feel; plus, Boston's many famous landmarks are a major draw for tourists, like the Bunker Hill Monument , the home of Paul Revere, Fenway Park (the home of the Boston Red Sox) , The Freedom Trail , and Boston Common . Visitors to the area can partake in tours of the U.S.S. Constitution , The Boston Tea Party Ships and Museum , and Old North Church .

Boston is known for being quite pricey when it comes to accommodations and entertainment, so it's best to budget accordingly. Parking and traffic can also be a challenge. However, Boston is a walkable city, so it's easy to leave one's vehicle behind and explore on foot.

Cape Cod, Massachusetts

Enjoy fantastic restaurants, hundreds of miles of seashore, and historic museums.

Many look at Cape Cod, Massachusetts, as an idyllic and tranquil seashore destination that allows for adequate relaxation and an opportunity to take in the historical and cultural significance of the area. Located on Route 6A, a historic highway that has achieved National Scenic Byway Status , Cape Cod is home to many different lighthouses, whale-watching recreation, optimal hiking and birdwatching, and multiple art museums.

Those who stop in Cape Cod can particularly enjoy the Cape Playhouse for local theater performances and the Cape Symphony for timeless musical concerts.

• Distance: 70 miles from Boston
• Road Trip Length: Approximately 90 minutes

Providence, Rhode Island

Locals refer to providence as "the creative capital" due to its small-town charm and simultaneous big-city vibes.

Although it is well-known as the smallest state in America, Rhode Island isn't one that should be ignored. The tiny spot on the map packs in over 400 miles of coastline, earning Rhode Island the nickname "The Ocean State" . Located next to the Atlantic Ocean, vacationers will have their fair share of freshly caught seafood to enjoy during their visit.

Besides food, there are plenty of fun things to do in Providence as part of a New England road trip itinerary; stop at the Roger Williams Park Zoo for a day of exploring or go for a ride with Providence Kayak . Locals and guests alike will also appreciate the many local boutique shops and community events.

• Distance: 82 miles from Cape Cod

Related: 10 Beautiful Coastal Stops On A Road Trip In New England

New Haven, Connecticut

The ultimate blend of college town and seaside retreat.

New Haven, Connecticut, is the perfect blend of a college town and a seaside retreat. Younger generations come to advance their education while families, retirees, and vacationers appreciate the beauty the Long Island Sound provides to the area. With the addition of Yale University , the Ivy League establishment has brought multiple museums to the city, including the Yale University Art Gallery, Yale Center for British Art, and the Yale Peabody Museum.

Other points of interest within New Haven include public parks. Two of the most popular recreational areas include East Rock Park and Lighthouse Point Park . Another top contender is Edgerton Park , which is built on a demolished historical estate.

• Distance: 102 miles from Providence
• Road Trip Length: Approximately one hour and 45 minutes

The Berkshires, Massachusetts

Discover this mountain area's museums, orchards, breweries, wineries, and festivals.

There are many small towns and villages that make up the area that is called The Berkshires in Massachusetts. For those looking to learn more about the area, The Berkshires boasts over 100 cultural attractions . People visit the mountain area throughout the year, enjoying various recreational activities in different seasons.

There are many local festivals to take part in during a visit. Depending on the timing of the visit, there are ample orchards, breweries, and wineries to enjoy. Visitors also rave about the local boutique shopping, the Susan B. Anthony Birthplace Museum , Edith Wharton's Home , and Berkshire Art Museum .

• Distance: 78 miles from New Haven

Brattleboro, Vermont

Experience farm-to-table restaurants, a focus on all things local, and beautiful landscapes.

Another one of the fun stops on a New England road trip is the town of Brattleboro, previously known as Brattleborough , which is most commonly known to locals by the simple nickname of "Bratt".

One of the unique aspects of Brattleboro is that it's home to one of the top circus performance schools, NECCA . Visitors can also participate in activities frequently hosted on Retreat Farm ; this farm conservation effort is on 500 acres of forests, farms, trails, and waterways. Whether it's a guided round of "Hike and Seek" or craft beer and cheese tastings, people of all ages are bound to find a suitable activity.

• Distance: 93 miles from The Berkshires

Brattleboro, Vermont, is known as "one of the best small towns in America" and was the winner of the 2023 Strongest Town Award .

Burlington, Vermont

For those keen on ice cream and teddy bears, this stop is a dream come true.

The city of Burlington, Vermont, has an array of attractions to enjoy in a day when visiting as part of a New England 10-day road trip itinerary. The city boasts tons of amenities that suit any age; people can easily pack their days full of fun activities and sightseeing between the beautiful beaches, the various breweries, parks, and shopping centers.

Just a short drive away, road trippers can find the iconic Ben and Jerry's ice cream factory and the Vermont Teddy Bear Factory . Both attractions offer tours for a nominal fee. Visitors should not forget to check out the flavor graveyard at Ben and Jerry's, where the company has laid to rest their retired ice cream combinations.

Plus, a visit to Burlington isn't complete without checking out the Church Street Marketplace shopping center and the scenic overlooks sprinkled throughout the area.

• Distance: 151 miles from Brattleboro
• Road Trip Length: Approximately two hours and fifteen minutes

Related: 10 Cozy Towns To Retire To In Vermont

Bar Harbor, Maine

Although this leg is by far the lengthiest, a pit stop in this coastal town opens up acadia national park.

Home to Acadia National Park, the coastal area of Bar Harbor is outstanding for nature enthusiasts and is easily one of the best stops on a New England road trip route. Visitors have endless opportunities to enjoy hiking, swimming, biking, running, and more during a short stay in Bar Harbor. For those who aren't inclined to participate in such activities, the views of Acadia National Park are also worth the long drive.

Nature aside, Bar Harbor offers much more for locals and tourists to enjoy during their time in the city. The Seal Cove Auto Museum is a top destination, as well as The Natural History Center . Visitors can also enjoy a guided tour of the area through Oli's Trolley and participate in one of the many ghost walks that uncover the past of Bar Harbor.

• Distance: 339 miles from Burlington
• Road Trip Length: Approximately six and a half hours

Portland, Maine

By blending the present with the past, this waterfront city offers a combination of charm and innovation.

Next on the 10-day road trip itinerary for New England is Portland in Maine , which has a history of agriculture and shipbuilding; those two elements are still very present today. Nestled on a peninsula that enters the Casco Bay, visitors will be mystified by the laid-back approach to life that the locals enjoy. The waterfronts are home to many fishing piers that bring fresh seafood to the top-notch restaurants in the city, and the historical homes pay homage to the area's past.

Visitors can hop on a ferry that takes them around Casco Bay. A visit to Portland's many attractions , such as the Portland Observatory and Portland Museum of Art, gives a unique perspective to the cultural scene that is very prevalent in the area. To learn more about the beginnings of Portland, guests should pop into the Maine Historical Society for insight into the early days.

• Distance: 175 miles from Bar Harbor
• Road Trip Length: Approximately three hours

Portsmouth, New Hampshire

Take a break from the car with a visit to this walkable, historic city on the seacoast.

This walkable city on the coast is another one of the fantastic New England road trip stops. As one of the oldest cities in the United States, Portsmouth was settled in the early 1600s by founder John Mason. Today, the area has many attractions that speak to its unique elements and humble beginnings.

Visitors can enjoy the Strawberry Banke Museum, the Seacoast Science Center, and a tour of the Portsmouth Historic Sites, which include the former residences of prominent navy commanders and officials. Other noteworthy activities include a ride on a Portsmouth harbor cruise or taking in a show at The Music Hall.

• Distance: 52 miles from Portland
• Road Trip Length: Approximately one hour

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Mami’s yaki onigiri are grilled rice balls worth getting to know

The Japanese snack gets filled with different ingredients at the Portland restaurant.

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Mami’s yaki onigiri. Photo by Peggy Grodinsky

I was introduced to onigiri, and yaki onigiri, 35 years ago when I lived in Japan. For years after I returned to the States, I could rarely find either, and onigiri was among the foods I missed most. Now, onigiri (sometimes, in Hawaii, called omusubi) have caught on in the U.S., but yaki onigiri remain – at least in my experience in Maine – harder to find. “Yaki” means grilled in Japanese; “onigiri” are rice balls, so these are, you got it, grilled rice balls, although often, as at Mami, they’re in the shape of a triangle.

Typically in Japan, onigiri have a small knob of filling – things like pickled plum or spicy tuna – whereas yaki onigiri are not filled. At least that’s how I remember it. But Mami fills its yaki onigiri, and I am not complaining.

At lunch one day late last month, that filling was a small amount of carrots and garlicy sweet potato rendered with pork fat. The yaki onigiri was brushed with a soy-miso glaze and chili crisp (that last also non-traditional) before it was grilled. After the snack had burnished to a deep, caramely brown, it arrived at my table, nice and warm and scattered with scallions and furikake. I broke it open with chopsticks: The medium-grain rice was moist, chewy and soft all at once, the crispy crust a perfect contrast. If “umami” were a smell rather than a taste, it’d smell like this did.

Mami, a lunch and dinner cafe, says it sells about 30 yaki onigiri a day in the winter, double that come summertime. Other recent fillings have included spicy salmon and beef with shishito peppers. In Japan, I encountered yaki onigiri mostly on nights out drinking and sharing small plates of Japanese bar food. You eat them with very fresh oshinko (Japanese pickles), said my friend Dan, who grew up in Japan, worked there for years and speaks fluent Japanese, explaining, “at the end of the meal to absorb all the alcohol. The capstone.”

For me, yaki onigiri bring back memories of (specifically) dark, snug izakayas under the train tracks in Tokyo, and (generally) being young and carefree and on a grand adventure.

And Mami’s yaki onigiri are delicious.

Yaki onigiri, $7; Mami, 339 Fore St., Portland, 207-536-4702, mamiportland.com

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