boston trip day

How to Spend One Perfect Day in Boston, MA (Itinerary + Tips!)

Boston is one of our absolute favorite cities in the USA, and luckily, even one day in Boston, MA is enough to get an overview of what makes the city so special!

We once spent a delightful summer living in Boston, and return visits have continued to leave us increasingly enchanted with the city.

With its gorgeous architecture, deep ties to American history, and impressive walkability, Boston is incredibly fun to explore, whether you have a mere 24 hours in Boston or months to uncover Beantown’s best attractions.

We designed this one day Boston itinerary to help you discover as many of the city’s highlights as possible in a single day–all of which are found along a walkable route!

The famous Freedom Trail, the charming North End (also known as Boston’s Little Italy), stately Beacon Hill, and the bustling Market District are all touched on here, and our hope is that you say goodbye to Boston already excited to plan your next visit.

Here’s how to see the best of Boston in a day!

Table of Contents

The Perfect One Day in Boston Itinerary

What about the freedom trail, where to stay in boston, ma, more than 24 hours in boston, getting around during one day in boston, quick tips for seeing boston in a day, read more about visiting boston (and new england), your one day boston itinerary map.

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Start your morning in the Boston Public Garden.

The Boston Public Garden is one of our favorite places in the city and the perfect place to kick off your day in Boston.

The garden is quiet and beautiful, and it’s a great place to relax, take a walk, and enjoy a bit of peace in the midst of the hustle and bustle of the city.

With only 24 hours in Boston (or less, if you’re planning a day trip to Boston) you don’t need to spend long here, but it’s worth stopping by and makes a convenient starting point.

Be sure to check out the Make Way for Ducklings Statue, put in place for the famous children’s book that features Boston, while you’re there! If you’d like to enjoy views of the Public Garden from the water, the swan paddle boats in the garden’s pond are famously inexpensive at $3.00/ride.

Stroll through the Boston Common and enjoy views of the Massachusetts State House.

Located right next door to the Public Garden, the Boston Common is the heart and soul of the city.

Established in 1634, it’s the oldest public park in the USA–though the surroundings are quite a bit different than they were back in the 17th century!

Today, the Common is extremely centrally located, and within a few minutes walk from here you can be in Beacon Hill, in Back Bay, at the Massachusetts State House, in the Theater District, shopping at Downtown Crossing (where you’ll find all the standard chain stores), or exploring a piece of American history (which, of course, the Boston Common itself also is).

The park is gorgeous to walk through–be sure to take in plenty of views of the gold-domed Massachusetts State House while you’re there!

Meander through Beacon Hill, one of the prettiest places to visit in Boston.

Located directly north of the Boston Common (more or less behind the state house), Beacon Hill is widely considered one of the most beautiful neighborhoods in Boston and is my personal favorite to explore.

This is where you’ll find the Boston that you see on postcards: redbrick mansions, black shutters, a cobblestone path or two, tree-lined streets.

We recommend walking from Boston Common up to Louisburg Square, which boasts some of the most prestigious addresses in Boston (former Secretary of State John Kerry lives here).

From there, take a quick stroll to Acorn Street to take advantage of one of Boston’s most photogenic spots.

Just be sure to be cognizant of the residents as you snap photos!

Beacon Hill is a very residential neighborhood, and while photos and admirers are generally welcome, blocking doorways and climbing stoops is not.

Stop by Park Street Church and the Granary Hill Burying Ground.

After enjoying a bit of time in Beacon Hill, head back down to Boston Common and pay a visit to the Park Street Church and Granary Burying Ground, which are located right next door to the Common.

While you can see the bulk of the cemetery from the street, it’s a shady, peaceful spot, and worth a quick peek inside (only a quick one, though: this one day Boston itinerary features a somewhat outsized number of burying grounds).

As you step inside, you’ll notice a large monument with a very familiar name in Granary Burying Ground!

Benjamin Franklin’s parents are buried here, and a monument to the family is erected toward the center of the cemetery.

Visit King’s Chapel and Burying Ground.

The King’s Chapel is my favorite church in Boston to go inside–not because it is ornate, but because it is so unusual among US churches.

Built originally as an Anglican Church in the 18th century, the church has enclosed “boxes” instead of rows of pews.

Originally, prominent families who were members of the church would have a box of their own that they would sit in each Sunday.

The King’s Chapel still has an active congregation–but these days, instead of Anglicans, Unitarians call the chapel home.

Sample the original Boston Creme Pie at the Omni Parker House.

Think you need to make a reservation and sit down to a meal to eat the original Boston Creme Pie?

You definitely don’t!

The Omni Parker House has a small shop on the first floor selling the delicious cakes, and stopping to pick one up is a great way to sample the flavor without eating up too much of your one day in Boston (pun intended).

If you want to also try the original Parker House rolls (which are, in fact, delicious), then consider following in the footsteps of Ulysses S. Grant, John F. Kennedy, Franklin D. Roosevelt, and many more by planning a meal ( or even an overnight stay ) at the Omni Parker House as well.

Stop to admire the Old Corner Bookstore.

The former home of Anne Hutchinson has acted as a bookstore, an apothecary, a private home, a Boston Globe souvenir shop, a diamond store, and now a Chipotle: talk about evolution!

The building is still worth a nod as you go by, though (and is officially part of the Freedom Trail, despite its concurrent status as a place to grab a burrito).

The Old Corner Bookstore also happens to be set right across from the Irish Famine Memorial–a striking statue worth taking a look at during your day visiting Boston.

Pay a visit to the Old State House and the site of the Boston Massacre.

As the oldest surviving public building in Boston, the Old State House has seen more than its fair share of American history!

This building was once the seat of the colonial government, then became the seat of the Massachusetts state government, and eventually Boston City Hall.

And, of course, it was the site of an important moment in the American Revolution: the Boston Massacre, which is commemorated with a plaque in the exact location of the altercation.

The Old State House has been a museum since the 19th century, after more than 100 years in public service and a brief stint as a commercial building.

As you wander your way through Boston on your way to the Old State House, be sure to note the Old South Meeting House along the way!

Head to the Boston Market District to browse (and snack).

The Market District is easily one of the most iconic places to visit in Boston, and a must-see when sampling Boston in a day!

Made up of several markets that are found in very close proximity to each other, there have been markets operating in this area since at least 1743.

Starting with the most famous (though not necessarily the best place to shop), keep an eye out for:

Faneuil Hall Marketplace

Made up of closely located Faneuil Hall, Quincy Market, South Market, and North Market, this is the heart of Boston’s historic market district.

It’s also one of the most touristy places in the USA, comparably with places like Fisherman’s Wharf in San Francisco or Navy Pier in Chicago .

It’s definitely worth stopping by this historic spot during your day in Boston, but we wouldn’t recommend spending long here (and based on the usual levels of crowds, you probably won’t want to).

Boston Public Market

Looking to purchase some New England specialties, whether to devour immediately or to take home as souvenirs?

Boston Public Market is the perfect spot for that: featuring exclusively New England-based products and companies, you can pick up anything from produce to donuts to crafts here.

This is one of my favorite spots in Boston–and not just because of how good the ice cream is!

If you’re lucky enough to have your 24 hours in Boston overlap with a Friday or Saturday, be sure to swing by Haymarket (located right in front of the Boston Public Market) to check out a fabulous farmer’s market!

Pause at the New England Holocaust Memorial.

Right in between the Boston Public Market/Haymarket area and the Faneuil Hall Marketplace sits the sobering New England Holocaust Memorial.

It takes very little time to walk through–no line, no entrance fee–but is absolutely worth taking a moment to slow down and appreciate.

Make your way into the North End for some sightseeing.

Boston’s North End (also known as “Little Italy”, though you won’t catch a local calling it that) is the oldest neighborhood in Boston and a fascinating sort of place.

Once a neighborhood popular with Italian immigrants, today it is more popular with tourists thanks to its beautiful architecture, many historic sights, dozens of restaurants, and famous pastry shops.

Here are a few things to be sure to check out when visiting the North End!

Paul Revere House

The oldest remaining building in downtown Boston once belonged to none other than Paul Revere!

Whether you head inside for a tour as part of your one day Boston itinerary, or simply admire the facade as you stroll by, be sure to note this piece of American history sitting in the North End.

Old North Church

And speaking of Paul Revere…

The whole “one if by land, two if by sea” story?

That lantern was said to have been hung here, at the Old North Church (which also happens to be the oldest church in Boston that is still standing today).

You’ll find a statue of Paul Revere on his horse nearby as well.

Copp’s Hill Burying Ground + The Spite House

Boston’s second-oldest cemetery holds more than 1200 marked graves that include plenty of notable burials from the colonial era… but that’s not the only reason to visit.

Right across the street from Copp’s Hill Burying Ground sits the Spite House (also known as the Skinny House), which is home to one of my favorite Boston stories.

As the story goes, two brothers inherited land from their father.

While one was away serving in the American Civil War, the other brother built a large home, taking over part of the soldier’s inheritance.

When the soldier returned home, he built the “Spite House”–incredibly skinny, and yet incredibly effective at blocking his brother’s view.

The legitimacy of the story is somewhat questionable, but it’s a classic Boston tale.

Enjoy an Italian-American dinner in the North End.

While the North End is indisputably touristy today, it still serves up incredible Italian-American food… if you know where to look.

Like many iconic neighborhoods around the world, you’ll find a mix of mediocre-to-terrible tourist traps and delicious restaurants here, so it’s imperative to check reviews before sitting down!

We have loved our experiences at both Ristorante Euno and Tresca (pictured below: everything was delicious, but their house special of chicken parm made with vodka sauce was a standout!).

Not in the mood for Italian-American food?

I can’t say I understand, but you do have options!

The Bell in Hand Tavern (the burger is one of my favorites) and the Union Oyster House are both Boston classics that you can find nearby, and Neptune Oyster is another excellent option (I’m not an oyster fan and found plenty of tasty options when visiting).

More into ambiance than anything and not ready to hang up your sightseeing hat?

A scenic dinner cruise on the Boston Harbor might be right for you!

Book your dinner cruise on the Boston Harbor today!

… and some classic pastries for dessert!

If you’ve heard one thing about eating dessert (and specifically cannoli) in the North End, it’s probably about how delicious Mike’s Pastry is.

If you’ve heard two things, it’s probably that Modern Pastry is better and more “unknown”.

Here’s what we can tell you firsthand: Modern Pastry is tasty (though it’s no longer unknown and getting more popular every day), and the line at Mike’s Pastry is always too long for us to bother with (though we’ve heard from others it dies down sometimes–if you visit in the winter, you might get lucky!).

Looking for something slightly further off the beaten path?

We found the beautiful Caffé Vittoria thanks to my stepmom (a Boston local of 30 years) and it’s now our go-to pastry spot in the North End, with great prices, a beautiful interior, and delicious desserts.

If you know of one attraction in Boston, it’s probably the Freedom Trail.

This famous 2.5-mile sightseeing trail covers 16 historical sights related to American history in Boston and it is easily (and deservedly!) one of the most popular things to do in the city.

So don’t worry–it’s definitely on the list!

In fact, the vast majority of the  16 sights on the Freedom Trail  are covered as part of this one day Boston itinerary, including the Boston Common, Park Street Church, King’s Chapel, Faneuil Hall, every historical sight I discuss in the North End, and more.

By following this Boston itinerary, you’ll spend quite a bit of time walking the Freedom Trail, and you’ll have tons of opportunities to check out the brick markings that denote where it leads!

Rather than simply list something so vague and malleable as part of the itinerary, though, we wanted to be sure to give specific suggestions.

After all, the trail can be seen in any order and doesn’t need to be seen all at once!

With only 24 hours in Boston, you likely won’t be able to tour the interior of each building, but you’ll see them from the outside and can pick and choose which ones to enter.

With only 24 hours in Boston, we recommend staying somewhere close to a Boston T (metro) stop that is near the center of the action.

The North End is a tempting option, but it is fairly difficult to get in and out of.

Back Bay or the Historic Downtown area along the Freedom Trail are both ideal places to stay.

The Theatre District (near Downtown Crossing and Chinatown) is another solid option with a great central location.

If budget is an issue, you may need to go a bit further out. That’s not a problem–just make sure you’re within walking distance of a T stop!

For budget travelers not willing to sacrifice on location, the HI Boston Hostel is a great option.

Mid-range travelers will love the location (and breakfast) at the Boston Park Plaza .

Want access to a kitchenette in your room? Copley House features some studios and apartments!

For travelers looking to splurge, the Boston Omni Parker House Hotel has it all: history, a prime location on the Freedom Trail, plenty of ambiance, and of course, the original Parker House rolls and Boston cream pie served right on-site.

Check rates & book your stay in Boston today!

If you’re lucky enough to have more than 24 hours in Boston, it’s safe to say that you absolutely will not run out of things to do!

With a full weekend in Boston or more, the first things we’d recommend adding on would be plenty of time exploring the neighborhood of Back Bay, getting out on the water with a whale-watching cruise or harbor cruise , and visiting at least one museum.

Boston is chock full of world-class museums, but you can’t go wrong with the Isabella Stewart Gardner Museum (the Venetian-style building alone is worth a visit, and the museum is famously the victim of a heist ), the Museum of Science, or the Boston Tea Party Ships and Museum (especially if you’re visiting Boston with kids, but it’s fun for all ages).

Other fun things to do in Boston include visiting Fenway (or even attending a Red Sox game), saying hello to the penguins at the New England Aquarium, or digging into some of Boston’s hidden gems and visiting quirky attractions like the Mapparium (one of the most memorable maps we’ve ever laid eyes on!).

If you’d like to complete the Freedom Trail, the USS Constitution, and the Bunker Hill Memorial are both a bit further from the city center than the attractions covered in this one day Boston itinerary, but they’re well worth a visit!

And, while it doesn’t make sense with only 24 hours in Boston, if you are staying longer and checking out some of the above attractions, be sure to price out a Boston Go Card to see if it can save you money on your trip!

Here’s our full guide to 55 cool things to do in Boston.

Thanks in large part to the fact that Boston’s historic core was built long before horseless carriages took over the roadways, the best things to do with a day in Boston are found surprisingly close together!

This entire one day in Boston itinerary is found along a walkable route that takes about an hour in total to cover, though that depends highly on how much you meander in places like the Boston Common and Beacon Hill (and meandering is truly one of the best parts of visiting Boston).

Walking doesn’t appeal?

If so, the wildly popular Boston Duck Tour or a Hop-On/Hop-Off Bus Tour might be right for you.

If you want to trim just some walking, or need an efficient way to get back to your hotel at the end of the night, Boston’s subway system (the T) has several stops near this route that you can take advantage of.

If you’re driving into the city for the day, there’s a very convenient parking garage right under the Boston Common that will deliver you more or less right to the starting point of this Boston itinerary.

Alternatively, you could park in a garage outside the city center and take one of the commuter rails into the city (less convenient, but generally less expensive and allows you to avoid driving into the city center).

Pick and choose your indoor attractions (weather permitting).

This itinerary for Boston mentions several buildings-turned-small-museums that don’t take long to step inside individually, but add up to eat up a decent chunk of your day (and in the case of some, your wallet).

For places like the King’s Chapel, Old South Meeting House, Paul Revere’s House, etc., we’re assuming that you’ll see each from the outside as you walk the Freedom Trail, and pick and choose which to enter based on your personal sightseeing style.

And, you may be more inclined to spend more time inside museums on a winter day than a summer one!

Tickets generally run between $5 and $15 per adult for each attraction.

Some Freedom Trail attractions, like Faneuil Hall , the Boston Common, and the burying grounds, are free to visit.

Don’t want to walk? Consider a Duck Tour.

Cheesy? Yes.

Entertaining? Absolutely.

Boston’s Duck Tours are famous for the unmistakable truck-slash-boat contraptions that they cart tourists around in by both land and sea, and they’re very popular with visitors of all ages.

Corniness aside, if you’re looking for an excellent way to get an overview of Boston’s most famous sights and history without too much walking, a Duck Tour might be the right choice for you!

The tours do sell out, especially in the summer, so be sure to book in advance if you want to make a Duck Tour part of your 24 hour Boston itinerary!

Book your duck tour in Boston today!

… but wandering is at least half the fun.

I truly can’t overstate this enough: Boston is one of the absolute best cities in the US to explore on foot (personally, I’d say Savannah is the other city closest to its level, with places like New York , Charleston , and New Orleans also ranking extremely close).

If you arrive in Boston with dry weather and no mobility issues, wear your most comfortable shoes and spend the day hitting the pavement!

You’ll see and experience much more on foot in Boston than you would any other way, and hopefully have a lot of fun as you do.

Keep the season in mind.

Boston is an extremely seasonal destination, with sightseeing crowds peaking in the summer and fall (when the fall foliage is at its best in New England, the crowds are plentiful in Boston).

… but Boston can be enjoyed year-round.

Summer and fall may be most popular, but there are benefits to visiting Boston year-round… as long as you’re willing to bundle up!

Winter, while cold and dark, is a much less crowded time to spend a day in Boston (and it’s much easier on the wallet).

Spring brings temperamental weather, but increasingly longer days and the fun of watching the city wake up.

With a big enough coat and thick enough boots, we’d be happy to visit Boston year-round.

Make your dinner reservations in advance.

This itinerary for Boston in a day suggests having dinner in Boston’s famous North End… and while the experience is absolutely worth it, you don’t want to show up without a reservation!

The neighborhood’s restaurant scene is incredibly popular, and without planning ahead, you may end up finding yourself without a table–or worse, at a tourist trap restaurant rather than a delicious one.

Same-day or next-day reservations are generally all that’s needed on weekdays and/or if you’re willing to eat on the early or late side, but ideally, it’s best to plan at least a couple of days in advance (or longer if you’re heading out on a summer Saturday night and are hoping to nab a table at a trendy new place).

Planning a trip to Boston soon, and want to keep reading?

You can browse all of our 100+ USA blog posts here , or check out these guides:

• 55 Best Things to Do in Boston (+ Travel Tips!)
• 21 Best Places to Visit in New England
• 17 Fun Weekend Getaways from Boston
• 15 Amazing Things to Do in Acadia National Park
• 15 Wicked Fun Quotes About Boston

Take This Map With You! Click each highlight to pull up the name of the destination. To save this map to “Your Places” on Google Maps, click the star to the right of the title. You’ll then be able to find it under the Maps tab of your Google Maps account! To open the map in a new window, click the button on the top right of the map.

About Kate Storm

In May 2016, I left my suburban life in the USA and became a full-time traveler. Since then, I have visited 50+ countries on 5 continents and lived in Portugal, developing a special love of traveling in Europe (especially Italy) along the way. Today, along with my husband Jeremy and dog Ranger, I’m working toward my eventual goal of splitting my life between Europe and the USA.

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The 16 best day trips from Boston

Take a break from city life and visit these nearby New England destinations—no packing required

While many of us could easily spend every waking moment in Boston, it can be refreshing to escape the city for 24 hours or so. Fortunately, this picturesque New England region offers an array of potential day trips from Boston, including quaint seaside villages, historic towns and stunning mountain vistas. So grab your pals or significant other, and hop on a ferry, train or automobile to one of these lovely destinations. Once you're back in town, you'll once again feel ready to take advantage of the  best Boston attractions ,  best free things to do in Boston  and  best museums in Boston . And when you need a little longer time away check out our list of the best weekend getaways in New England . RECOMMENDED: The Best Hotels in Boston

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Best day trips from Boston

1.  Newport, RI

The Newport mansions of the Gilded Age still impress with their grandeur—just as they were built to do. If you have time to only tour one estate, check out The Breakers . Near the International Tennis Hall of Fame , the Audrain Auto Museum houses a seasonally rotating display of incredible cars inside a gorgeous Art Deco building.

Take the Cliff Walk, which has stunning views of the ocean, or relax at the public Easton’s Beach . Stroll past cool shops and eateries on narrow Thames Street. On Marlborough Street, dine at the White Horse Tavern , which claims to be America’s oldest restaurant, or duck over to The Reef at Howard Wharf for dinner and drinks with a view. Near the harbor, Bowen’s Wharf’s buildings date back to the 1700s, now offering an inviting maze of restaurants and shops. Stroll over the causeway to Goat Island where the Newport Harbor Lighthouse is overlooked by the upscale Gurney’s Resort.

2.  Portland, ME

​​Maine's largest city, located about a two-hour drive north of Boston, attracts epicureans from around the country to its cobblestone streets. Wander the charming, hilly Old Port district, where every kind of boutique imaginable touts colorful wares. Pop into one of the many quaint pubs and dimly lit cocktail bars, like the excellent Jewel Box or Blyth & Burrows —the latter of which pairs the best in innovative mixology with equally scrumptious small plates. In the West End arts district, enjoy the I.M. Pei-designed Portland Museum of Art and the State Theatre , which hosts national acts, both musical, comedic and theatrical.

The food scene here lives up to the hype:   Cong Tu Bot for nationally celebrated Vietnamese fare;  Green Elephant for an inventive vegetarian meal;   Evo Kitchen + Bar for progressive twists on Mediterranean cooking; or  Union , a vibrant locavore haunt located at  The Press Hotel , whose historic building was formerly the home of the Portland Press Herald.

3.  Newburyport, MA

The Newburyport Historic District, which encompasses most of the downtown, is listed in the National Register of Historic Places. This treasure trove of well-preserved, Federal-period architecture includes the notable Cushing House Museum & Garden , home of statesman Caleb Cushing, and the Custom House Maritime Museum , which also unravels local history. The beautiful Waterfront Park and boardwalk has regular concerts during warmer months.

Catch a play or see a show at the Firehouse Center for the Arts , grab a gourmet sandwich and bottle of wine at Joppa Fine Foods ,  relax with excellent cocktails and modern Middle Eastern bites at Bar25 ,  dine on classic seafood at The Black Cow  or head to the Newburyport Brewing Company ,  offering a friendly tap room and beer garden.

Newburyport includes part of neighboring, sedate Plum Island , a barrier island overlooking salt marshes.

4.  Gloucester, MA

Shipbuilders and fishermen put Gloucester on the map, and both industries still exist there today —just  on a smaller scale. The Fishermen’s Memorial on Gloucester Harbor honors all those lost at sea, including the Andrea Gale and its crew, the real-life victims of The Perfect Storm . Check out the Cape Ann Museum , which has an amazing collection of art and artifacts specific to Gloucester and its surroundings.

Across narrow Main Street, you can savor straight-off-the boat seafood at the chic basement restaurant  Tonno . Oak to Ember  will impress with its menu of hearty, wood-fire-cooked dishes and thoughtful cocktails. Or, if you're more about ocean views, head to the Beauport Hotel , whose 1606 Restaurant has a great deck overlooking the water. Next door to the hotel, Beauport Cruise Lines offers seasonal jaunts around the harbor.

5.  Salem, MA

Salem is forever linked to its horrifying and fascinating 1692 Witch Trials. The curious flock to the home of presiding Judge Corwin, which today is a museum known as The Witch House . Halloween is a big thing here—so are new age and cult shops. On a less spooky note, the Peabody Essex Museum houses a wonderful art collection, and Salem is the birthplace of Nathaniel Hawthorne, author of The House of the Seven Gables. You can even tour the house he may have been writing about, the 350-year-old Turner-Ingersoll Mansion.

Though it only dates back to 1930, Pioneer Village —a 10-minute drive from downtown, in Forest River Park—reenacts early 17th-century colonial life. Eat like a local at Ledger or Settler , or nerd out with old school arcade games and pinball machines at Bit Bar . 

6.  Provincetown, MA

Creative, sassy P-Town—located only a 90-minute ferry ride from Boston—is an artsy LGBT hotspot. It’s got a great mix of galleries, restaurants and nightlife hangouts. Lined with dozens of colorful shops, friendly eateries and local businesses, Commercial Street is the bustling heart of the town. Seek out one of the many events and festivals that fuel the thriving arts scene.

The famous and seasonal  Lobster Pot is the biggest name in town for classic lobster rolls and fresh seafood treats. Climb the 252-foot granite Pilgrim Monument for dramatic harbor views, then escape to Race Point Beach to enjoy the sights, sounds and smells of the open ocean.

Eat innovative seasonal dishes at Strangers & Saints and great seafood at Mac’s Fish House , which has crispy fish and chips and Happy Hour dollar oysters. Explore the beautifully barren Outer Cape’s stretch of the Cape Cod National Seashore , including Truro’s picturesque Highland Light .

7.  Ogunquit, ME

Set on the breathtaking Maine coast, Ogunquit is a popular, classic beach town with a quiet ambiance, particularly in the cooler months when crowds disappear. But it’s also a historic arts community; the Ogunquit Museum of American Art was started in the 1950s by native artist Henry Strater, a student of Ogunquit’s Perkins Cove artists colony.

Wander the galleries around town, explore the Barn Gallery on Shore Road and get tickets to a show at the Ogunquit Playhouse —which boasts eight decades of professional theatre and summertime children’s productions—or another summer stock theater.

8.  Watch Hill, RI

A coastal village that’s part of the town of Westerly, Watch Hill has one of the best beaches on the East Coast, and celebrity glamour to spare. Get to town early and take a walk out on the Napatree Point Conservation Area , where  you’ll find the remains of Fort Mansfield and lots of beautiful birds like osprey and piping plovers.

After your nature walk, head into the charming town for a stroll and some shopping. The kids will love the vintage carousel, and be sure to have lunch at the Olympia Tea Room (supposedly Taylor Swift’s fave—you can take a peek at her house from afar, too, because it’s hard to miss). Finish the day with cocktails at the gorgeous Ocean House , where you can have a drink and a bite to eat.

9.  Concord, MA

Stroll to the Old North Bridge and explore the Minute Man National Historical Park’s five-mile Battle Road Trail, dedicated to the Battle of Concord (April 19, 1775), where militia engaged with British troops and ignited the Revolutionary War. The 19th-century Transcendentalist movement and its influential authors and thinkers—Ralph Waldo Emerson, Henry David Thoreau and Bronson Alcott—were rooted in Concord, and the Concord Museum is a good place to connect the dots. Located just outside of Concord Center are Walden Pond , which honors Thoreau’s famed naturalist journal, and Orchard House , where Louisa May Alcott wrote Little Women 150 years ago.

Pick up a picnic lunch at The Concord Cheese Shop . The Saltbox Kitchen’s tasty dishes and small-batch brewery are both fueled by produce from its nearby Saltbox Farm. For dinner, Woods Hill Table  also sources from their own farm at Woods Hill in Bath, NH, and the sleek, seasonally-focused 80 Thoreau is worth the day trip alone.

10.  Providence, RI

Providence is a foodie’s dream. Why does this small capital city have so much kitchen talent? Nearby Johnson & Wales University’s College of Culinary Arts is a major factor. Hemenway’s downtown is the grand dame of area seafood restaurants;  Waterman Grille is a vibrant jewel on the East Side near Brown University; and Aleppo Sweets is a lauded Syrian bakery and cafe—just to name a few spots. Federal Hill, the city’s impressive Italian neighborhood, is also loaded with Italian eateries and shops. 

Waterplace Park is a lovely gathering spot, and it anchors the city’s annual WaterFire program, which runs from spring through late fall; braziers along the Providence River are lit at sunset and stoked with aromatic wood by black-clad figures on boats, while themed music plays.

Providence is home to the notable Trinity Repertory Company , and The Strand Ballroom & Theatre, one of the nation’s best rock venues. The Rhode Island School of Design’s museum includes one the country’s finest university art collections.

11.  Mystic, CT

Settled in 1654, Mystic was once a shipbuilding seaport village. Now, it's a quintessential New England town, packed with mom-and-pop shops and activities for the whole family to do. 

During warm weather, spend a few hours on the sea with a day sail or sunset cruise from Argia Mystic Cruises , or visit the famous Mystic Aquarium or the Mystic Seaport Museum .  

After working up an appetite, stroll through the village to see the famous weighted Bascule bridge . P ick up a sweet treat from award winning Sift Bake Shop  and  splurge on a Connecticut lobster roll at the The Shipwright's Daughter  or a hearty, grass-fed burger at the Engine Room .  And, if you must eat pizza in Mystic, head to Nana’s Bakery and Pizza for inventive takes on personal pies.

12.  Falmouth, MA

Falmouth is nestled on the southwestern part of Cape Cod, 20 miles south of the Sagamore Bridge. Lined with great beaches, cool boutiques and relaxing spots to eat and drink, it's also one of The Cape’s easiest towns to get to. Do breakfast or lunch like a local at The Pickle Jar Kitchen .

The Falmouth Museums on the Green brings 1700s Cape Cod to life; the Federalist home of Dr. Francis Wicks is wonderfully preserved and packed with original artifacts. The Shining Sea Bike Trail ,  which hugs the coast and brings you past lovely views of both the Vineyard Sound and Buzzards Bay, runs from Falmouth to Woods Hole. The trail’s name comes from “America the Beautiful,” the famous poem by Katherine Lee Bates, a Falmouth native. (Though once a railroad, the path follows ancient Wampanoag Indian trails.) One more highlight: the Woods Hole Oceanographic Institution Ocean Science Discovery Center .

13.  Lexington, MA

The best part of taking a day trip to Lexington? You can easily do it by bicycle by traveling down the Minuteman Bikeway , which begins in North Cambridge and runs right through the leafy suburb, some 15 miles northwest of Boston. This posh town is most famous for its historic Battle Green , where the bloody Battle of Lexington took place and patriotic Minute Men engaged the British Army on Lexington Common. Many of the original homes flanking the battleground are preserved, including one that serves as a visitor’s center.

Stroll Lexington Center’s mom-and-pop shops, enjoy homemade ice cream at Rancatore’s or dine at il Casale   from local chef Dante de Magistris, who draws from his family’s roots to make handmade pastas, delicious sfizis and classic dishes, all in a rustic-chic atmosphere. For an elegant Sunday brunch or dinner, The Inn at Hastings Park’s Town Meeting Bistro  is a modern pleasure involving sleek, seasonal dishes.

14.  Kittery, ME

Kittery, while most famous for its shopping, has so much more to offer. First stop: Bob’s Clam Hut , a 60-year-old roadside diner that serves incredible fried clams, sustainable local fish and amazing milkshakes. Next stop? Yes, shopping at the adjacent Kittery Premium Outlets , whose stores include everything from discounted Calvin Klein to Lindt chocolate.

Also known for the historic Portsmouth Naval Yard —which is in Kittery, not neighboring Portsmouth, NH—this sleepy town includes Tributary Brewing Company , which has a cool tasting room and live music on weekends.

The heart of Kittery Foreside, which is the downtown area, is Wallingford Square and it's dotted with all kinds of restaurants including the sleek bistro Anneke Jans  and casual asian eatery  Anju Noodle Bar . Or  stop by Lil’s Café , a quaint spot set in a former bank whose old walk-in safe is now its Vinyl Vault, a small alcove with used records for sale. Lil’s bakery downstairs turns out some of the best pastries in New England and excellent chai, too.

15.  Washington, CT

For a small town in rural Connecticut, Washington has a big reputation for its arts and architecture. The Judy Black Memorial Park and Gardens is set in a once-abandoned gas station and boasts lovely landscaping and revolving art exhibits.

Every July, the Litchfield Jazz Festival takes place at venues around town and world-renowned modern dance company Pilobolus holds its Five Senses Festival . In September, Gilmore Girls fans take over—the town inspired the beloved TV program’s fictional Stars Hollow. Surrounded by colonial architecture, you can shop at unique boutiques and treat yourself to dinner (and a room, for a real spurge) at the historic, luxurious Mayflower Inn .

16.  Stockbridge, MA

Just off I-90, Stockbridge is the gateway to the beautiful Berkshires, part of the Taconic Mountains. Main Street is home to the venerable Red Lion Inn , a one-time frontier town tavern that maintains a casual eatery called Widow Bingham’s Tavern, as well as a gorgeously original main dining room with traditional favorites and an award-winning wine list.

Nature and art dominate the area: Just off Park Street, behind Main Street, take the wooden footbridge and walk the Laurel Hill Association’s beautiful trails. Visit the Norman Rockwell Museum and see where the renowned illustrator and artist lived and worked. Nearby, visit Chesterwood , the home of the Lincoln Memorial sculptor Daniel Chester French, and Naumkeag , a Gilded Age architectural masterpiece. A few miles away in Lenox is the Tanglewood Music Center , the Boston Symphony Orchestra’s summer home. Nearby, you can take a guided tour of Edith Wharton’s home, The Mount , and learn about the woman behind the building and the books.

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Boston Itinerary: How to Spend Five Days in Boston

One of the most historic cities in the United States , Boston is the city I called home for the first 25 years of my life.

More a collection of towns than a metropolis like New York , Boston is a city steeped in history (it contains a lot of historical firsts for the United States and played a pivotal role in its founding), delicious food, wide-open green spaces, first-rate museums, and warm, welcoming people.

Visiting Boston offers all the benefits of a big metropolis without the intensity and fast pace of New York.

Boston is easy to get around and compact, making it perfect for travelers. The subway will take you wherever you need to go.

So how many days do you need to visit Boston?

Most people visit for three to four days, and I think that’s a perfect amount of time. As someone who’s lived there, I can say that, since Boston is so small, you won’t waste a lot of time “in transit,” so you can pack a lot into your days. Obviously, you can spend longer here (slow travel is the best travel), but for the first-time visitor, three to four days is enough.

Here’s a suggested Boston itinerary that will allow you to see the best of Boston:

Table of Contents

Boston Itinerary: Day 1

Boston itinerary: day 2, boston itinerary: day 3, boston itinerary: day 4, boston itinerary: day 5, other things to see and do in boston.

• Boston Common
• Massachusetts State House
• Park Street Church
• Granary Burying Ground
• King’s Chapel Burying Ground
• Benjamin Franklin statue and the former site of Boston Latin School
• Old Corner Bookstore
• Old South Meeting House
• Old State House
• Site of the Boston Massacre
• Faneuil Hall
• Paul Revere House
• Old North Church
• Copp’s Hill Burying Ground
• USS Constitution
• Bunker Hill Monument

You follow a brick road through the city, and there are signs and historical markers all along the way. Given all the walking that’s involved, I would make this the main activity of the day. You’ll want to take your time and see all the sites thoroughly.

You can also take a guided tour from the visitor’s center. Tours run hourly between 11am and 1pm, with additional tours in the afternoon in the spring and summer. Tickets are $17 USD for adults, $15 USD for students and seniors, and $8 USD for children 6-12 (free for kids under 6).

4 S Market St, +1 617-523-1300, faneuilhallmarketplace.com. Open Monday-Saturday 10am-9pm and Sunday 12pm-6pm.  

Browse for Books Located a stone’s throw away from the Boston Common, Brattle Book Shop is a family-run used bookstore that dates back to 1825. It’s actually one of the oldest surviving bookstores in the country! It’s home to over 250,000 books, maps, postcards, and other odds and ends. In addition to used books, the store is also home to an impressive collection of first editions and antique books.

9 West Street, +1 617-542-0210, brattlebookshop.com. Open Monday-Saturday 9am-5:30pm.

Walk Around the Back Bay This area used to be an actual bay. Before the Europeans arrived, the indigenous population used the tidal bay to catch fish, as the bay drained completely during low tide. When the land was colonized, a dam was built and the tidal bay was eventually filled in, creating the Back Bay area.

The end of the Public Gardens meets Boston’s Back Bay, our version of New York’s SoHo and West Village. This is where Boston’s elite and wealthy live, and nearby Newbury Street is our Madison Avenue, with lots of expensive shopping and high-end eateries. It’s a beautiful space to stroll around, with pretty brownstones and tree-lined streets. You can still see plenty of old Victorian homes in this neighborhood that date back to the 19th century. ( Here’s a list of other neighborhoods worth checking out as well!

You’ll also find the Boston Public Library here. Opened in 1852, it’s one of the largest municipal libraries in the country, home to over 23 million items, with almost 4 million visitors each year.

206 Clarendon St, +1 617-536-0944, trinitychurchboston.org. The church is open for prayer and tours Tuesday-Saturday 10am-5pm and Sundays 12:15pm-4:30pm. Tours are $10 USD for adults, though it is free to enter for worship.

Head up to the Prudential Tower Head back toward Copley to see the Prudential Tower, colloquially known as “The Pru.” You can actually go up to the top and get a bird’s-eye view of Boston. There are 52 floors in the building, which was built in the 1960s. These days, it’s the second tallest building in the city (the John Hancock Tower is first).

800 Boylston St, +1 617-859-0648, prudentialcenter.com. Open daily from 10am-8pm (10pm in the summer). Admission is $34.99 USD for adults, with discount available for students, seniors, and children.

47 David G. Mugar Way, +1 617-626-1250, hatchshell.com. See the website for an up-to-date list of events.

1 Science Park, +1 617-723-2500, mos.org. Open Saturday-Thursday 9am-5pm and Fridays 9am-9pm. Admission is $29 USD for adults, with discounts available for seniors and children.  

1 Central Wharf, +1 617-973-5200, neaq.org. Open Monday-Friday 9am-5pm, weekends 9am-6pm. Admission is $34 USD for adults, with discounts available for kids and seniors.

See the Skinny House When you’re in the North End, visit 44 Hull Street. Known as “the Skinny House” (or the Spite House), this incredibly narrow house has a rather interesting history. Built after the Civil War, it was a passion project of Joseph Euestus, who came home from the war to find that his brother had taken over more than half of the inherited land they were meant to share. Joseph decided to build on the remaining land — which his brother thought was too small to build anything on. Joseph went ahead and built a narrow four-story home on the small slice of land to block his brother’s view.

Visit an Art Gallery or Museum Boston has a lot of great galleries and museums, so depending on your interest, you’ll want to check out some (or all) of the galleries and museums below. It will take more than an afternoon to see them all but you can always spread these visits out over a few days!

• Institute of Contemporary Art : If contemporary art is your cup of tea, this is for you. While it’s not my favorite style of art, I have to admit this place does put on some insightful exhibits. 25 Harbor Shore Drive, +1 617-478-3100, icaboston.org.
• Commonwealth Museum : This museum explores the history of Massachusetts. It’s actually really interesting and entirely underrated (especially if you’re a history nerd like me). 220 Morrissey Blvd, +1 617-727-2816, sec.state.ma.us/arc.
• Harvard Museum of Natural History : This natural history museum has exhibitions showcasing dinosaurs, animals, and minerals (including meteorites). It’s a great choice if you’re traveling with kids, though there is plenty of informative content for adults too! 26 Oxford St +1 617-495-3045, hmnh.harvard.edu.
• Harvard University Art Museums : Harvard actually has three art museums – the Fogg Museum, the Busch-Reisinger Museum, and the Arthur M. Sackler Museum. They are home to both modern and historical art exhibitions. See what exhibitions are running by checking their website. harvardartmuseums.org
• Museum of Fine Arts : This museum has an impressive collection of over 450,000 pieces of fine art. It also runs all sorts of art classes throughout the year, both multi-week classes as well as single-day workshops. If you’re looking to learn something new or improve your skills, check out the website for more details. 465 Huntington Avenue, +1 617-267-9300, mfa.org.
• Warren Anatomical Museum : Founded in 1847, this macabre museum is filled with Civil War–era medical tools as well as some unique (and perhaps unsettling) medical mysteries. It’s super weird but super neat. A definite must if you’re looking for an off-the-beaten-path museum! 10 Shattuck St, +1 617-432-6196, countway.harvard.edu/center-history-medicine/warren-anatomical-museum.
• Boston Tea Party and Ships Museum : This interactive museum is home to some historic ships that have been authentically restored to show you what life was like at sea during the Boston Tea Party. It also has a really informative documentary about the events that led up to the Tea Party and the American Revolution. Best of all, you can actually throw fake crates of tea into the river yourself to see what it was like! 306 Congress St, +1 617-338-1773, bostonteapartyship.com.
• Paul Revere House : Built in 1680, this is actually the oldest building in the entire city (it’s been renovated but it’s still the original building). The museum is filled with the family’s furniture and artifacts, giving you a sense of what life was like in Boston before the Revolution. 19 N Square, +1 617-523-2338, paulreverehouse.org.
• Museum of Bad Art : The name says it all! This is a museum filled with terrible art. The MOBA has rotating exhibits throughout the year, so there is always something new and terrible to behold. If you feel like a laugh, definitely check out this quirky gallery! 55 Davis Square, +1 781-444-6757, museumofbadart.org.
• Isabella Stewart Gardner Museum This museum is home to an amazing art collection of over 20,000 items, including European, Asian, and American art. Opened in 1903, the museum is made up of a wide-ranging collection of paintings, tapestries, decorative arts, and sculptures. It’s one of the best museums in Boston. Don’t miss it. 25 Evans Way, +1 617-566-1401, gardnermuseum.org.

Harvard University, +1 617-495-1000, harvard.edu/on-campus/visit-harvard/tours.

125 Arborway, +1 617-524-1718, arboretum.harvard.edu. Open daily 7am-7pm. Admission is free.

Take the Sam Adams Brewery Tour After four days of sightseeing, you deserve a beer or five. Luckily, this brewery is located near the Arboretum so it’s easy to visit and a great way to end your day. Sam Adams is a major brewer in Boston, and locals drink it widely and frequently. The brewery offers free tours, starting in mid-afternoon and departing every 45 minutes. You get a few free samples along the way. If you’re under 21, don’t worry. You can still go — you just can’t drink.

30 Germania St, +1 617-368-5080, samueladams.com. Tours are available Monday-Thursday and Saturdays 10am-3pm. On Friday, tours are available between 10am and 5:30pm. Their Sam Signature Experience is 45 min long and costs $10 USD.

4 Yawkey Way, +1 877-733-7699, mlb.com/redsox/ballpark. See the website for an up-to-date schedule.

(The Sox not in season? No worries. We have the Bruins, Celtics, and Patriots. No matter the time of year, you’ll be able to find a game to see!)  

Visit the Children’s Museum If you’re traveling with kids, this is a great place to spend part of your visit. It’s the second oldest children’s museum in the US and has permanent exhibits on health and exercise, construction, space, art, and diversity. It also has a real two-story house from Kyoto, Japan, that teaches kids about life there (it’s actually pretty cool!).

308 Congress Street, +1 617-426-6500, bostonchildrensmuseum.org. Open Wednesday-Sunday 9am-12pm and 1:30pm-4:30pm. On the first Saturday of the month, the museum opens at 10am. Admission is $20 USD for both adults and kids (free for infants under 12 months).

Charlestown Navy Yard, +1 617-426-1812, ussconstitutionmuseum.org. The ship is open Tuesday-Sunday 10am-6pm (with extended hours in the summer); the museum is open 10am-6pm (with extended hours in the summer as well). Admission is free, though the museum has a suggested donation of $10-15 USD.

Visit More Museums – With any extra time, visit more museums! There’s plenty of them to see! Try not to skip the big ones!

725 Commonwealth Avenue, +1 617-353-2630, bu.edu/astronomy/community/open-night-observatory/. Viewings are Wednesday evenings at 7:30pm in the autumn and winter and 8:30pm in the spring and summer. Make sure to get there 10 minutes early as they don’t permit entry once it starts.

See the Mapparium – Located in the Mary Baker Eddy Library, this three-story inverted globe serves as a giant map of the world that you can walk into via a glass bridge. It is constructed of over 600 stained-glass panels and shows the world as it looked in 1935.

200 Massachusetts Avenue, +1 617-450-7000, marybakereddylibrary.org. Open daily 10am-5pm. Admission to the Mapparium is $6 USD for adults, with discounts available for students, children, and seniors.

Head to Castle Island – Castle Island is located in South Boston and is famous for Fort Independence. When the fort was no longer needed for defense, it was actually used as the first state prison. The island covers 22 acres and has excellent beaches, as well as some running trails that are popular with the locals. There’s also an area for picnics and you can visit the old fort for free. The place gets pretty busy on the weekends during the summer, and you can often see school groups exploring the fort during the spring.

Relax at the Lawn on D – This massive green space is new to the city (when I was growing up, there was nothing in this area so you would never go there). There are all sorts of free activities happening year-round, from concerts to festivities and everything in between! There’s public seating, free Wi-Fi, art exhibitions, and a few games, like table tennis and bocce. To see what events are happening during your visit, check the website for details.

420 D St, +1 877-393-3393, signatureboston.com/lawn-on-d. Open Monday-Wednesday & Friday-Saturday from 7am-11pm and Thursday & Sunday from 7am-10:30pm (hours may vary for events). Admission is free.

Hike the Blue Hills – This park is a bit out of the way, but it’s definitely worth a visit if you want to get out and stretch your legs. The 7,000-acre park is home to over 100 miles of trails and offers some picturesque viewpoints. There are also plenty of activities to keep you entertained, such as boating, fishing, skiing, and rock climbing (depending on the season). It can get busy in the summer on the weekends, so just be sure to arrive early.

Tour the Custom House – Built in the 17th century, the Custom House is one of the most recognizable buildings in the city. In 1915, a tower was added to the building, making it the tallest building in the city at the time. The building is owned by Marriott Hotels now, though you can still take a free tour (by appointment) to go up to the observation deck on the 26th floor.

3 McKinley Square, +1 617-310-6300, marriott.com/hotels/travel/bosch-marriott-vacation-club-pulse-at-custom-house-boston. Tours are free though they are by appointment only.

Boston is a great city (and I’m not just saying that because I grew up there). I’ve never encountered a person who hasn’t liked it. This Boston itinerary will give you a good overview of the city at a relaxing pace. You’ll be moving around a lot, though, so make sure you get an unlimited “T” pass (subway/train pass). If you have more time, you can squeeze in some other activities .

But why rush such a beautiful place?

Take it slow. Mix and match the itinerary to suit your needs but this is how I’d structure my days if I was visiting Boston!

Book Your Trip to Boston: Logistical Tips and Tricks

Book Your Flight Use Skyscanner to find a cheap flight. They are my favorite search engine because they search websites and airlines around the globe so you always know no stone is left unturned.

Book Your Accommodation You can book your hostel with Hostelworld as they have the biggest inventory and best deals. If you want to stay somewhere other than a hostel, use Booking.com as they consistently return the cheapest rates for guesthouses and cheap hotels.

For the best hostels, check out this post on the best hostels in the city.

If you want to know the best neighborhoods, here’s my guide to all the best areas in town !

Don’t Forget Travel Insurance Travel insurance will protect you against illness, injury, theft, and cancellations. It’s comprehensive protection in case anything goes wrong. I never go on a trip without it as I’ve had to use it many times in the past. My favorite companies that offer the best service and value are:

• Safety Wing (best for everyone)
• Insure My Trip (for those over 70)
• Medjet (for additional evacuation coverage)

Looking for the Best Companies to Save Money With? Check out my resource page for the best companies to use when you travel. I list all the ones I use to save money when I’m on the road. They will save you money when you travel too.

Want More Information on Boston? Be sure to visit our robust destination guide on Boston for even more planning tips!

Got a comment on this article? Join the conversation on Facebook , Instagram , or Twitter and share your thoughts!

Disclosure: Please note that some of the links above may be affiliate links, and at no additional cost to you, I earn a commission if you make a purchase. I recommend only products and companies I use and the income goes to keeping the site community supported and ad free.

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Boston   Travel Guide

1-day Itinerary in Boston

• 1-Day Itinerary
• All Things To Do
• 2-Day Itinerary
• 3-Day Itinerary

Boston Public Garden Boston Public Garden free

Though the Boston Public Garden sits right next to Boston Common , the two are quite different. The public garden is newer (established in 1837) and holds the distinction of being America's first public botanical garden. Flowers and trees are beautifully organized and kept in quality condition throughout. You can see the colorful arrangements and exotic trees from the 6-acre pond as you glide along the water in a Swan Boat. Additionally, the park houses two of Boston's most iconic statues: Make Way for Ducklings (a bronze sculpture of a duck and her eight ducklings) and a sculpture of George Washington (which shows America's first president riding on a horse).

Visitors looking to relax after sightseeing will enjoy the Boston Public Garden. Parkgoers say you'll find plenty of shade beneath the park's trees, which comes in handy on hot summer days. Plus, you'll likely spot some ducks and geese swimming around the lagoon. And if you have a few dollars, visitors recommend taking a 15-minute ride on a Swan Boat. The large paddle boats cost $4.50 to ride (or $3 for kids ages 2 to 15 and $4 for seniors); travelers with Go Boston Cards ride for free. Swan Boats are usually available between mid-April and Labor Day.

Boston Common Boston Common free

The grounds of Boston Common started as a cow pasture in the mid-1600s. It was also used for Puritan punishments, like whipping, and even for hangings. In 1768, the area was transformed into a British camp. After the Revolutionary War, the park became a popular locale for public speeches and rallies. Now, the Common is best known because of its status as the oldest public park in the country. You'll also find a variety of activities and events – including theater and musical performances and free fitness classes – hosted here throughout the year. If you plan to traverse the Freedom Trail , you'll start the walk here at Boston Common.

Though some visitors say you won't find much to do in this park, Boston Common is great for picnics or a leisurely stroll. Travelers also mention that this site is a wonderful spot to take young children. In addition to ample running room on the park's green space, kids can play at the Tadpole Playground or Frog Pond. Frog Pond offers a spray pool during the warmer months and an ice skating rink in the winter. Some visitors do note that the park tends to draw Boston's homeless population, particularly at night.

Freedom Trail Freedom Trail free

Stretching 2½ miles, the Freedom Trail weaves past 16 of the city's most historic sites, including Faneuil Hall Marketplace , the Paul Revere House and Old North Church . Taking in all of the trail's attractions requires at least half a day (and some comfortable walking shoes), but you can easily plot points of interest before you begin your jaunt from Boston Common .

Though most visitors agree the trail is easy to navigate on your own, some recommend a guided tour or downloading an app to tell you about the sites. (You'll find a handful of apps available for Apple and Android devices.) If you have a Go Boston Card, standard guided tours given by the Freedom Trail Foundation are covered by your pass.

Faneuil Hall Marketplace and Quincy Market Faneuil Hall Marketplace and Quincy Market free

U.S. News Insider Tip: Every Friday and Saturday, Haymarket (one America's oldest open-air markets) pops up adjacent to Faneuil Hall. In order to navigate this often-chaotic scene successfully make sure to bring small bills, leave bulky bags at the hotel and keep it moving on the sidewalk. - Jill LeGrow

Four buildings – Faneuil Hall, Quincy Market, North Market and South Market – constitute Faneuil Hall Marketplace, with the oldest being Faneuil Hall. Built in 1742 and now a stop on the Freedom Trail , Faneuil Hall has had a long and important history in Massachusetts politics. Samuel Adams once stood here to push for resistance against the British, and abolitionists and suffragists have stood on their soapboxes here. In fact, this is where colonists famously challenged the Stamp Act of 1764 by proclaiming, "no taxation without representation." From those illustrious days, the marketplace has expanded to include more than 100 shops and restaurants.

New England Holocaust Memorial New England Holocaust Memorial free

Gaze up at the six 54-foot glass towers that comprise the New England Holocaust Memorial, and you're bound to be awestruck. Dedicated in 1995, each haunting tower is etched with numbers. The 6 million numbers represent the Holocaust's victims, while the towers represent the six major death camps. There is also a granite path covered in quotes from survivors that leads visitors inside the towers.

Recent visitors described walking through the columns as an emotionally charged and unforgettable experience. The monument's location next to Faneuil Hall Marketplace makes it very accessible while walking the Freedom Trail .

Paul Revere House Paul Revere House

For a glimpse of what life was like in the late 1700s, head to Paul Revere's former residence in the North End . The house, which is situated on the Freedom Trail , offers insight into how homes looked in Revere's time (it's even filled with period pieces, including fine silver). Inside, history fans can admire the building's sweeping beams, spacious fireplaces and some original furnishings owned by the Revere family.

If you like American history, travelers say you'll enjoy seeing the Paul Revere House. This house is small, though, so don't allot more than an hour to tour the property. Docents are friendly and knowledgeable.

Old North Church Old North Church

Most people who know anything about American history have heard of Paul Revere's famous midnight ride, when he rode through town to warn people about the arrival of British troops. Before heading off to Lexington, Revere gave orders at Old North Church. Robert Newman – the church's sexton – and Captain John Pulling Jr. – the church's vestryman – then climbed the steeple and held two lanterns as a signal that the British were indeed coming, but by sea.

The church itself, which is officially named Christ Church, is filled with beautiful relics from the past, including North America's oldest set of change ringing bells and chandeliers brought in from England in the early 1700s. The pews have a long history as well; Pew No. 54 was reserved for Paul Revere's son.

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THE 10 BEST Day Trips from Boston

Day trips from boston.

• Boston to Concord
• Boston to Salem
• Boston to Newport
• Boston to Plymouth
• Private Day Trips
• Up to 1 hour
• 1 to 4 hours
• 4 hours to 1 day
• 5.0 of 5 bubbles
• 4.0 of 5 bubbles & up
• 3.0 of 5 bubbles & up
• 2.0 of 5 bubbles & up
• Chinese (Simplified)
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• The ranking of tours, activities, and experiences available on Tripadvisor is determined by several factors including the revenue generated by Tripadvisor from these bookings, the frequency of user clicks, and the volume and quality of customer reviews. Occasionally, newly listed offerings may be prioritized and appear higher in the list. The specific placement of these new listings may vary.

1. Martha's Vineyard Daytrip from Boston with Round-Trip Ferry & Island Tour Option

2. Boston to Plymouth Day-Trip including Quincy, Plimoth Patuxet and Mayflower II

3. The Small Group Boston Tour, I know secrets that others don't!

4. Martha's Vineyard Day Trip with Optional Island Tour from Boston

5. New York City Day Trip from Boston

6. Boston to Newport Small-Group Day Trip with Breakers & Marble House Admission

7. Boston to Coastal Maine & Kennebunkport Guided Daytrip with Trolley Tour

8. Day Trip from Boston To Salem Witch Exhibits

9. Boston and Cambridge Private Day Tour

10. Best of Boston Small Group Tour w/Boat Cruise + View Boston

11. Boston to Kennebunkport with Optional Lobster Tour

12. Boston Lexington and Concord Revolutionary War full day tour

13. Salem and North Shore Full Day Private Tour

14. Plymouth & South Shore Full Day Private Tour from Boston

15. Private Tour of Lexington, Concord, and Boston

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These Are the 30 Best Things to See and Do in Boston

With historic sights, beloved hometown sports teams, a thriving arts scene, and local brews and bites, you'll never be bored in Boston.

Boston is consistently ranked as one of the top 10 most-visited cities in the United States — and for good reason. Home to a thriving food and drink scene, historic landmarks, and activities for all types of travelers, the city offers plenty to keep visitors occupied. So, whether you're on a solo adventure or traveling with the whole family, here are 30 of the best things to do in Boston.

Walk the Freedom Trail.

The two-and-a-half-mile, self-guided Freedom Trail tour takes visitors through the city, telling the story of the American Revolution with stops at museums, churches, meeting houses, and other historical markers along the way. Do it alone, or find tour options here .

Step back in time at the Paul Revere House.

Want even more Boston history? Head to the Paul Revere House . The home, which was once owned by Revere and sold in 1800, served as everything from a boarding house to a local shop to tenement apartments. Now, it's a museum offering guided tours of the restored home that will transport you back in time.

Stroll through the Boston Common.

The Boston Common is the very heart and soul of the city. First built in 1634, it is the oldest public park in the United States. On the park's 50 acres of land, guests will find the Frog Pond, a softball field, and monuments galore. Take your time strolling through the landscaped gardens and enjoying the sights.

See the animals at the New England Aquarium.

For more than 50 years, the New England Aquarium has invited guests to come and meet a few of the coolest sea creatures on Earth. From penguins to sharks, stingrays to seals, and everything in between, the aquarium has all kinds of animals for curious visitors. It's also a working research aquarium, meaning visits and donation dollars partially go toward ocean conservation and preserving these species for generations to come.

Take the kids to the Franklin Park Zoo.

For even more animal adventures, pay a visit to the Franklin Park Zoo . The 72-acre zoo is the place to be for a red panda, tiger, or zebra sighting right in the middle of the city. There are also plenty of expert-led chats to attend, as well as children's events, making it a place the entire family will love.

Or, see animals in their natural habitat with a whale-watching tour.

Take to the waters outside of Boston for a high-seas adventure like a whale-watching excursion . Hop aboard a tour with the New England Aquarium and Boston Harbor City Cruises to see whales, dolphins, and sea birds on their migration routes — all from a safe distance, of course.

Go for a walk around the Esplanade.

Another worthy place for a stroll is the Esplanade, a three-mile path that hugs the Charles River. It's an excellent spot for a walk or bike ride along the lovely green spaces on the banks of the river, where you can watch boaters. And if you're so inclined, you can donate to the Esplanade Association , a nonprofit working to preserve the space for more than two decades.

Violet Smirnova/Travel + Leisure

Take to the Charles River.

You may feel inclined to get on the water yourself — and you can do just that by joining Community Boating Boston on a sail. The organization offers sailboat, kayak, and stand-up paddleboard rentals for those feeling adventurous.

Watch a midnight movie at Coolidge.

The Coolidge Corner Theater, which first opened its doors during the golden age of cinema in 1933, is already one of the most incredible places to see a movie in the city. But to up the ante, try and visit for one of its After Midnite showings. The late-night programming includes horror films and off-beat flicks, making it great for an after-dark fright.

Visit the Isabella Stewart Gardner Museum.

Isabella Stewart Gardner was a woman who knew what she liked. She was a millionaire, a bohemian, and an intellectual, and the museum bearing her name is a gem of Boston's thriving art scene, with luxurious landscaped grounds. Perhaps some of the museum's most famous works aren't hanging on the walls, though, as eagle-eyed visitors can spot empty frames that once held priceless pieces, stolen from the space in a famed art heist in 1990.

Spend a day at the Institute of Contemporary Art.

The iconic Institute of Contemporary Art is housed in 65,000-square-feet of space, making it a spot where you can easily spend an entire day. The institute includes gallery exhibits, a theater, and a cafe, along with a gorgeous outdoor deck so you can get a breath of fresh air and reflect on all the works you've just seen. Plus, admission to the institute is free on Thursdays after 5 p.m., but make sure to snag your timed ticket in advance.

See the Arnold Arboretum.

The Arnold Arboretum of Harvard University is a living museum of trees and plant life, with a particular focus on flora and fauna from eastern North America and Asia. This National Historic Landmark is open every day and always free for visitors.

Scope out the treasures at The Museum of Fine Arts.

The Museum of Fine Arts is a crown jewel in Boston's museum scene. It includes American works of art and artifacts from around the globe, including pieces from across Europe, Asia, and Africa. The museum also holds collections in photography, musical instruments, textiles, and more.

Swing by Encore Boston Harbor.

Encore Boston Harbor is the place to go if you're looking for some good old-fashioned fun. The entertainment venue, which opened in 2019, includes a hotel, five-star dining options, shopping, and even a casino for those wanting to roll the dice and test their luck. Head out for a meal, stay for a game, and perhaps book an overnight stay so you can do it all again tomorrow.

Shop on Newbury Street.

Visitors to Boston could make an entire vacation out of just strolling down Newbury Street. The famed street is chock-full of boutique shops, restaurants, galleries, and more, so you may have to visit more than once to ensure you've seen and done it all. Keep track of pop-up events on the street's website here .

"Travel" the world at the Mapparium.

The Mapparium may just be the best way to "see" the world without ever leaving Boston. The three-story site is actually the world's largest walk-in globe. Guests can walk through the globe via a bridge dissecting its equator before leaving to check out "Our World: Mapping Progress," an exhibit highlighting "humanity's advancement since 1935."

Root for the Red Sox at Fenway.

There is arguably nothing more iconic in Boston than Fenway Park . If you visit during the regular baseball season, try to get tickets to a game. While inside, cheer for home runs over the Green Monster and get ready to sing "Sweet Caroline" at least once.

And cheer on the Celtics and the Bruins at TD Garden.

Visitors to Boston can continue to root for the hometown team by getting tickets to a Celtics or Bruins game, depending on the season. Luckily, both teams play under one roof at TD Garden , which also hosts plenty of concerts, so check the calendar to see what shows or games you can take part in next.

Grab a good book at the Boston Public Library.

When constructed in 1848, the Boston Public Library became the first large free public library in the nation. It remains a place where visitors can check out a good book or read in the public spaces. The library hosts both tours and regular events, so check its calendar and see what piques your interest.

Grab a bite at Boston Public Market.

The Boston Public Market , a year-round indoor marketplace, hosts nearly 30 New England-based food purveyors and artisans. It's also a place you can feel good about visiting, as it's a registered nonprofit with public impact goals to support "economic development, New England food system resilience, public health and education, affordability, and access."

Drink a local brew at Samuel Adams Boston Brewery.

Boston is home to a thriving craft beer scene, though the best-known spot for brews is popular brand Sam Adams. The company now sells its brews just about everywhere and even allows guests to come and taste its latest creations on a brewery tour. See all tour options here .

Devour dessert with a cannoli from Mike's Pastry.

There are plenty of excellent places to grab a cannoli in Boston's Italian mecca, the North End. Walk into any bakery in the neighborhood and you'll surely be delighted. But if you need a little guidance, we suggest heading to Mike's Pastry . It's the largest bakery in the neighborhood and wildly popular, but for good reason. Just be prepared to wait in line for your sweet treat.

Explore more city history on a walking tour of Chinatown.

In the 1880s, Chinese immigrants to Boston founded their own community, now known as Chinatown. The neighborhood has always played a significant role in the city's history and is a place where visitors can come to both learn and dine to their heart's delight. Hop on a Boston by Foot tour to ensure you see and dig in at all the right spots.

Watch a show at the Boston Ballet.

The Boston Ballet has delighted audiences since the 1960s, with performances ranging from classics like George Balanchine's "A Midsummer Night's Dream" and Mikko Nissinen's "Swan Lake," as well as modern pieces by William Forsythe, Jiří Kylián, Wayne McGregor, and more.

Waddle around on a Boston Duck Tour.

The Duck Tour may not have started in Boston, but the city has certainly perfected it. We'd be remiss not to mention this as a perfect Boston attraction for out-of-town visitors, as it goes to all the best city locations and even right onto the Charles River thanks to the amphibious vehicles. See all tour options here .

Shop and dine at Faneuil Hall Marketplace.

Want to pack as much Boston as you can into a single place? Simply head to Faneuil Hall . The famed marketplace is home to more than 70 retailers across its 200,000-square-foot space, including food, apparel, and specialty gift shops. It's a place to see and do it all, and it's especially magical if you can visit during the holiday season.

Learn something new at the Museum of Science.

Boston's Museum of Science may be one of the most fun spots in the city. It's filled with interactive exhibits that will surprise, delight, and leave you in awe. Head there to learn about the evolution of dinosaurs, see its exhibit on how vaccines work, and much more.

Stop by Trinity Church.

If you love architecture, design, and history, Trinity Church should be high on your list of things to see in Boston. A National Historic Landmark, the church is also considered by the American Institute of Architects to be one the country's top 10 buildings thanks to its Richardsonian Romanesque design and stained-glass windows. The church is open for both worship and tours throughout the week.

Get medieval at Castle Island.

Castle Island is a hidden gem that even locals tend to overlook. We're not quite sure how considering there is an entire castle-like fort hiding in plain sight. The 22-acre "island" isn't actually an island anymore after a small strip of land was added to connect it to shore, but that doesn't make it any less special. Visitors can come to tour the fort, walk the grounds, or head to its trails for a bit of rollerblading or biking.

Pick up new art at the SoWa studios.

Stroll through the SoWa studios and get a glimpse of the fantastic work from the city's artistic community. Visitors can swing by the first Friday of every month for open gallery tours or make an appointment with an artist to get up close to the works before buying.

The Perfect 3 Days In Boston Itinerary

Planning a trip to Boston? Welcome to one of my favorite cities in the United States. To help you have the best visit, I’m handing over the perfect 3 days in Boston itinerary.

This Boston itinerary takes you to all of the city’s must visit attractions, historic landmarks, charming neighborhoods, and world class museums. I also give you tips on where to eat, play, and stay.

I’m very familiar with Boston. I attended college at nearby Dartmouth, lived and worked in Boston, my daughter lived there, and my husband’s run in 4 Boston Marathons. I’ve likely walked every cobbled street.

I’m a hard core New England girl. And I love Boston, especially in the spring and fall.

The country’s oldest city, Boston is steeped in American history. Boston played a pivotal role in the Revolutionary War. Boston’s sometimes called the “hub of the world” or the “cradle of liberty” because it was the source and inspiration for key ideas that shaped America.

Boston is really a dream destination, especially for history buffs and culture vultures. It has a great foodie scene, wide open green spaces, quaint neighborhoods, and first rate museums.

Visiting Boston offers all the benefits of a big metropolis without the intensity and frenetic pace of New York.

Boston is easy to get around and compact, making it perfect for travelers. The subway will take you wherever you need to go. And Boston’s very walkable.

Before You Go: Here’s How To Plan Your Visit To Boston

Below are some of the top tours, hotels, and experiences in Boston. Donʻt forget to plan ahead!

Where To Stay:

• Kimpton Nine Zero
• Four Seasons
•   Ritz Carlton
• Whitney Hotel
• Charles Hotel

Best Guided Tours:

•   2.5 hour walking tour  of the Freedom Trail
•   2 hour guided walking tour  of the Back Bay 
• 1.5 hour guided tour of Harvard
• 3 hour food tour in the North End
• Boston sunset cruise

3 Days In Boston Itinerary

Let’s tour Boston in 3 days, taking in all its must see sites and some hidden gems. There’s so many things to do in Boston that you could be busy for a month.

But here are the attractions you simply can’t miss on your 3 day Boston visit. I recommend getting a Go City Boston all inclusive pass . It gives you skip the line access to over 40 attractions

Day 1: Hike the Freedom Trail

Start day 1 of your 3 day Boston itinerary at tiny Paramount near Boston Common. The diner is tucked into a street on Beacon Hill.

It’s a popular spot and there may be lines. After breakfast, you can embark on an activity that will take the entire day — hiking the Freedom Trail.

The Freedom Trail is a beloved 2.5 mile walk through historic Boston. It leads you through the major sites and monuments relating to the city’s founding and the Revolutionary War.

You follow a red brick road, with signs and historical markers along the way.

The trail begins in the Boston Common, the nation’s oldest park, and ends at Bunker Hill.

You can pick up a map and free guide at Faneuil Hall or the Boston Common Visitor Center at the beginning of the trail at 139 Tremont Street. Some stops are free and some charge admission.

Along the way, you’ll visit 16 historic Boston landmarks :

1. Boston Common — where the first white settler established a farm and the oldest city park in the US, dating back to 1634

2. Massachusetts State House — Federal style building with an iconic gold dome that celebrated independence, designed by America’s first professional architect Charles Bulfinch.

3. Park Street Church — where William Lloyd Garrison called for the abolition of slavery

4. Granary Burying Ground — the resting place of famous Patriots, including Paul Revere

5. King’s Chapel Burying Ground — burial grounds used by the Loyalists

6. Benjamin Franklin statue and a mosaic commemorating Boston’s first public school at Old City Hall

7. Old Corner Bookstore — once the epicenter of Boston’s literary life

8. Old South Meeting House — where Patriots triggered the Boston Tea Party

9. Old State House — seat of the British era colonial government

10. Site of the Boston Massacre — when British troops fired on tax protestors

11. Faneuil Hall — former political hotbed where Patriots gathered to protest British taxation, now Boston’s favorite marketplace

12. Paul Revere House — surviving house of the esteemed patriot

13. Old North Church — the launching pad for Revere’s famous Midnight Ride and where he arranged to have lanterns perched on the steeple warning that the Redcoats were coming

14. Copp’s Hill Burying Ground — resting place of the man who hung the lantern

15. USS Constitution — the ship known as Old Ironsides that survived British attacks, now a free museum

16. Bunker Hill Monument — granite obelisk marking the spot where the Patriots fought the British in the first pitched battle of the American Revolution

If you want to take a guided history and architecture tour of the Freedom Trail, click here to book one. You can also check out this 2.5 hour walking tour of the trail.

Stop for lunch at Faneuil Hall . Built in 1742, Faneuil Hall is the most visited destination in New England .

It has an open ground floor serving as a market, a covered assembly room above, and a grasshopper weathervane atop the roof. In the Revolutionary era, town meetings and ceremonies were once held in the assembly room.

You have tons of choices for lunch. You can get just about anything here. Since you’re in Boston, try clam chowder or a lobster roll, the local New England specialties.

If you’re not too tired from your long day of walking, consider taking in a concert at the Bottom Symphony Hall. The Boston Symphony Orchestra is one of the nation’s best, playing in a venue with world class acoustics.

Or head to a show at the Wang Theater , which showcases everything from dance to Broadway acts. Its lobby is opulent, built to resemble Versailles.

If you’re in the theater district, Yvonne’s is THE hipster restaurant in Boston. Have a classic cocktail turned out by the Library Bar and order some eats from the eclectic American menu with Asian and Mediterranean influences.

Day 2: Boston’s Neighborhoods: Fenway | Back Bay | South End

Start day 2 of your 3 day in Boston in the Fenway neighborhood. Fenway of course is known for its iconic ballpark. And the Red Sox have broken my heart more than once. But Fenway isn’t just a one trick pony. Fenway is home to some of the city’s best museums, music venues, and eateries.

Have breakfast at Tatte Bakery on Boylston Street. It’s a cozy rustic spot serving up delicious pastries, soups, and sandwiches. Alternatively, you can go to a Fenway landmark, Boston’s culinary delight Time Out Market. Try an haute couture donut at Union Square Donut.

Once you’re fueled up, visit one of the two most splendid museums in the Fenway area — the Museum of Fine Arts and the Isabella Stewart Gardner Museum . I love both, but am especially partial to the incredibly unique Gardner Museum. It’s one of the world’s best small museums .

Housed in a Venetian style palace, the exquisite Gardner Museum holds the in situ private collection of an eccentric heiress.

The museum has a real wow factor, with a skylit interior courtyard filled with sculptures and mosaics. Inside, the museum boasts an especially good Renaissance collection. There are art works by Rembrandt, Raphael , John Singer Sargent, Titian, and Veronese.

Here ‘s my complete guide to the Isabella Stewart Gardner Museum

The Boston Museum of Fine Arts is a world class museum that can be daunting to visit because it’s massive. Founded in 1876 and housed in a Beaux Art building, the museum was expanded by architect I.M. Pei.

The collection has everything from Egyptian mummies to minimalist Mondrians. If viewing fatigue sets in, head to the peaceful Shapiro Rotunda on Level 2 with classical murals by John Singer Sargent.

When you’re done museum-ing, cross the verdant Back Bay Fens Park and head to the Back Bay neighborhood. When strolling though the fens, you can stop and smell the roses at Victoria Garden and/or Kelleher Rose Garden.

2. Back Bay

Boston’s Back Bay is New England’s version of New York’s SoHo and West Village. And Newbury Street is the equivalent of Madison Avenue.

On Newbury, you’ll find lots of expensive shopping and high end eateries. You’ll want to stroll down Beacon, Marlborough, Commonwealth, Newbury, and Boylston streets.

It’s a beautiful space to meander, with pretty (can I move in?) brownstones and tree-lined streets. There are plenty of old Victorian mansions and churches in this neighborhood that date back to the 19th century. If you want to tour a brownstone, pop into G ibson Ho use Museum at 137 Beacon Street.

Back Bay’s churches are adorned with heavenly stained glass, perhaps the neighborhood’s greatest architectural asset. The most notable glass is in Arlingto n S treet Church . It boasts 16 stunning stained glass windows created by Louis Comfort Tiffany.

More Tiffany stained glass decorates the Church of the Covenant on Newbury Street. This church also houses the Gallery NAGA, featuring New England artists.

Another jewel in Back Bay is the Ayer Mansion at 395 Commonwealth Avenue. A registered historic landmark, the mansion is a rare surviving home created and decorated entirely by Tiffany.

His trademark stained glass windows shine above the front door, Inside, you’ll find beautiful glass mosaics, intricate woodwork, and a jaw dropping chandelier.

The piece de resistance, though, is the mosaic staircase in the entrance hall.

If you need a Back Bay art fix, visit the Galerie d’Orsay on Newbury Street. Even if you aren’t planning on purchasing a Picasso or Dali, pop in to see what’s on display.

The gallery has a range of old master, Impressionist, and modern art. It has special exhibitions throughout the year as well.

If you want, you can book a 2 hour guided walking tour of the Back Bay and other architectural landmarks in Boston. Or go on this 2 hour guided tour of Back bay and the Freedom Trail.

3. Copley Square

Next, head to Copley Square, a pretty public square in the Back Bay formerly known as the Art Square. There’s a little park where you can buy discount theater tickets, listen to musicians, and gaze up at the towering Hancock Tower. Every Tuesday and Friday afternoon, there’s a farmers market.

You should also peak into Boston’s Trinity Church in Copley Square. It’s Boston’s oldest and most beautiful church. It was built in the 1870s after the original building burned down in the Great Fire of 1872.

The style is known as Richardsonian Romanesque, which embraces the use of clay roofing and rough hewn stonework. Upon its completion, the church’s distinctive style influenced architects across the country because it was so beautiful.

You’ll also find the Boston Public Library here, the third largest library in the country. Opened in 1852, it’s one of the largest municipal libraries in the country — home to 24 million items and receiving almost 4 million visitors annually.

It’s designed in a palatial Renaissance Revival style. The library is famous for its murals. The most beautiful one is upstairs in the dimly lit Sargent Hall. You can take a free art and architecture tour of the library from its Dartmouth Street entrance.

Next head to the Prudential Tower, colloquially known as “The Pru.” There are 52 floors in the building, which was built in the 1960s.

If you’re hungry for lunch, stop in at Eataly in a nook of the Pru. It’s an Italian inspired oasis with shops, wine bars, dessert stands, and restaurants. You can pick up truffles, fine cheeses, pasta, and extra virgin olive oil.

4. South End

South End is a hipper version of Back Bay, and gets high marks for all things trendy. It stretches southwest along Tremont and Washington Streets to Roxbury.

South End’s glorious concentration of undulating Victorian row housing is unmatched anywhere in the US. In 1983, the entire area was listed on the National Register of Historic Places.

The area resembles Beacon Hill, probably because the street plan was laid out by the same architect, the very busy Charles Bulfinch. There are many beautiful squares.

The prettiest and grandest one is Chester Square. Much of the Victorian cast iron is botanical in form.

If you want to pop into the South End’s tony art galleries, stroll down Harrison Street.

While in the South End, don’t miss the Cathedral of the Holy Cross at 1400 Washington Street. Completed in 1875, it’s a vast Gothic Revival building. Its construction heralded the emergence of Catholicism in a previously predominate Protestant state.

A fantastic place for dinner in the South End is the hip and trendy Barcelona Win e B ar on Tremont Street. It serves up Spanish-centric tapas and small plates in an intimate setting.

The Beehive and SRV are also excellent choices.

Day 3: Cambridge | Beacon Hill | North End

1. harvard university.

On day 3 of your Boston itinerary, head to Cambridge and explore the historic Harvard University and soak in the feel of cloistered academia.

Founded in 1636, Harvard is the oldest university in America. Head to its home in Cambridge (Harvard Square train stop on the Red Line).

If you want breakfast or brunch in Cambridge, head to Cafe Luna, Curio Coffee, or Clover.

You can join a free Crimson walking tour or book your own 1.5 hour guided tour . You’ll learn about the revered university’s history, architecture, learning programs, and mythology.

Wander around and experience the mix of life in Harvard Square. There’s always street musicians. Stroll into used book stores and coffee shops.

Watch artists, vagabonds, locals, and college students mingle. There are some cool little shops in the mini-mall called the The Garage.

Step into Harvard Yard, the nucleus of the campus. Start at the Johnston Gate on Massachusetts Avenue. You’ll be greeted by a statue of John Harvard, which doesn’t resemble the man himself.

Ranged around the statue are tree lined footpaths, trim lawns, scholarly libraries, and elegant Georgian and Federal architecture.

Massachusetts Hall is the oldest surviving building. But it pales in comparison to Gothic Matthews Hall.

University Hall was designed by Bulfinch, and was the first building to veer away from Harvard’s trademark red bricks. The New Yard is dominated by the colonnaded facade of Widener Library.

Harvard has many art museums – the Fogg Museum, the Busch-Reisinger Museum, Arthur M. Sackler Museum, the Peabody Museum of Archaeology, and the Harvard Museum of Natural History.

The first three used to be separate but were recently combined under a single roof and renamed the Harvard Art Museums, after renovations from 2008-14.

If you only have time for one, I’d go to the Harvard Art Museums . The museum has a very good collection of Italian art, including pieces by Botticelli , Ghirlandaio, and Bernini .

You’ll also find paintings by a whole roster of Western art luminaries — Van Gogh, Picasso, Gauguin, Toulouse-Lautrec, Manet, and Rembrandt.

2. Beacon Hill

Then take the subway/taxi/Uber to colonial chic Beacon Hill. It’s an extremely pretty and exclusive neighborhood of gaslit streets and brick sidewalks.

The homes, many designed by the ubiquitous Bulfinch, were built for Boston’s Protestant merchant elite, known as the Boston Brahmins.

Start your tour of Beacon Hill at Louisberg Square. The smart bow front homes date from the 1830s.

Drop down nearby Willow Street and take in the cobblestoned Acorn Street, America’s most photographed street. For the grandest homes, head back up Mount Vernon Street. Bulfinch’s home is on Chestnut Street.

End your walk on Beacon Street. The bow front William Hickling Prescott home (#55) is a Bulfinch masterpiece open to the public.

You can also tour the Boston Athenaeum , one of the oldest independent libraries in the US, which was once the center of intellectual life in Boston.

Beacon Hill is also home to some beautiful hidden gardens. Founded in 1928, the Beacon Hill Garden Club opens their doors once a year on the third Thursday in May.

If you want to grab lunch in Beacon Hill before hitting your next destination, there are some amazing choices.

Beacon Hill has everything from upscale Italian to romantic restaurants to casual eateries. Try Moo (a modern steakhouse ), Figs (pizza), Toscano (Italian), or The Hungary I (French).

READ : Complete Guide To Beacon Hill

3. North End

After exploring Beacon Hill, head to Boston’s historic North End. This neighborhood is the heart of Boston’s Italian community.

The first Italians to arrive were Genoese in the 1860s. You’ll hear just as much Italian as you will Boston accents. It has a distinctly Mediterranean vibe.

The North End is the place to indulge. You’ll find the best gelato outside of Italy.

The best pastries can be found on Hanover Street (the main drag) at Mike’s Pastry or Bova , which vie for Boston’s best cannoli. And the best Italian food is at Giacomo’s Ristorante or Carmelina’s .

The lines are epically long at all these spots. But the wait is worth it.

Because of all these great spots, the North End is a fantastic place to take a food tour. You can book a pizza, food, and history tour or take this 3 hour tour by Secret Food .

When you’re done eating, be sure to visit Old North Church on Salem Street. It’s Boston’s oldest surviving church. It’s famous in Boston history.

Thanks to legendary messenger and patriot Paul Revere, two lanterns were hung from its steeple, alerting citizens that British troops were coming by sea. Around the corner is the Paul Revere House , which is well worth a visit to see how wealthy colonials lived.

The North End is also home to one of Boston’s quirky landmarks, the Skinny House on Hull Street. It’s only 10 feet wide. Legend holds that it was built out of spite, to block sunlight from the house behind it.

Tips For Spending 3 Days in Boston

Here are some must know tips for planning your 3 day Boston itinerary.

1. When Is The Best Time to Visit Boston?

I like Boston best during the shoulder season, spring and fall, when tulips and fall foliage delight the senses. Late August to early September is peak sunflower field season.

In late September to late October, you can pick apples at a plethora of farms around Boston and indulge in hot cider and sugary cider donuts.

But the summer can be beautiful too and isn’t always notoriously hot. Winter in Boston is fun, especially if you’re lucky and get a bout of fairly mild weather. You can enjoy Christmas lights, beautiful snowfalls, ice skating, and popup bars.

2. How To Get To Boston

To get to Boston, you can fly into Logan International Airport. The Massport shuttle bus will take you to the Blue Line terminal at Airport Station and you can ride that into town.

You can also take a taxi, Uber, or book a private transfer .

3. How To Get Around Boston

The best way to get around Boston is walking. Boston is a self-proclaimed walking city and is set out to encourage pedestrians.

If an attraction you want to see is too far afield, you can take the subway system nicknamed the “T.” Check out the subway map to plot your route.

There aren’t scads of taxis in Boston. But Uber works well and is what I use if I need to get somewhere fast.

There are other fun ways to explore Boston too. You can:

• book a 2.5 hour bike tour throughs the city highlights
• book a tour through Cambridge by bike
• take the hop on hop off trolley bus
• take a sunset harbor cruise
• take a Duck Boat tour down the Charles River
• or a 4 hour narrated driving tour

4. Mark Your Calendar: Major Events in Boston

Want to visit Boston for a special event? These are the special festivals you should keep on your radar:

• Boston Wine Festival : January through March
• St. Patrick’s Day Parade in South Boston: Sunday closest to St. Patrick’s Day
• Boston Marathon : third Monday in April
• Boston Calling Music Festival at Harvard Stadium: late May
• ArtWeek : late spring
• Cambridge Arts River Festival : early June
• Boston Pride Parade : second Saturday in June
• Boston Harborfest : July 4th weekend
• St. Anthony’s Feast in the North End: last Sunday in August
• Head of the Charles Regatta : last weekend in October
• SoWa Winter Festival : early December
• First Night : December 31

5. Where To Stay in Boston

If it’s your first time visiting, I would opt to stay in the downtown or Back Bay Area. Those areas are central to everything.

If you opt for downtown, I like the small XV Beacon or the Kimpton Nine Zero Hotel. You could also splurge at the Ritz Carlton or the Four Seasons .

The Inn at St. Botolph , the Lenox Hotel , and the Hilton in Back Bay are also nice options and central too.

If you can’t resist historic Beacon Hill, check out The Boxer , Liberty , or the elegant Whitney Hotel . If you want to stay in historic Cambridge, check out the luxurious Charles Hotel .

I hope you’ve enjoyed my 3 days in Boston itinerary. You may enjoy these other US city guides:

• 2 day itinerary for Montreal
• 1 day itinerary for Portland Maine
• 2 day itinerary for Philadelphia
• 3 day itinerary for Boston
• 1 day in Hanover New Hampshire
• 35 Landmarks in Boston
• 1 day itinerary for Cambridge
• Guide to Salem Massachusetts
• Guide To Boulder Colorado
• 1 day itinerary for Denver
• 2 day itinerary for Cleveland Ohio
• Best Things To Do in Pittsburgh

If you’d like to spend 3 days in Boston, pin it for later.

11 thoughts on “The Perfect 3 Days In Boston Itinerary”

Where is the best place to stay (hotel) for your 3 day tour of Boston?

It totally depends on your budget. I usually stay in Air Bnbs in the Fenway area when I visit, just because it’s close to my daughter. But if it’s your first time visiting, I would opt to stay in the downtown or Back Bay Area. Those areas are central to everything. If you opt for downtown, I like the small XV Beacon. The Inn at St. Botolph in Back Bay is nice and very central too.

Loved your itinerary! My husband and I are visiting Boston for a long weekend at the end of Sept and your ideas were greatly appreciated!!

Perfect time to go to Boston! Enjoy the city!

This is a really thorough and fantastic guide! You clearly know your stuff. Is there a printable version? Thank you!!

Hope you have a great visit! You can only just print it. I don’t have a special plugin for a printer friendly version. Sorry about that.

Ah, it brings back memories of living In the Fenway area for a yr while my husband attended Harvard Med School. Unfortunately we did not get to tour much, so would really like to go back and visit the many places you have described

Very Informative article. I have been planning to spend my vacation in Boston. But I was seriously confused as to where to stay, which places to visit, and what to eat. Your article cleared all my doubts and now I can plan my trip more efficiently and with much ease. Once again, thanks for such a detailed article

You’re welcome! Enjoy Boston.

What day should I add the Boston tea party and ships?

You can see it while you’re doing the Freedom Trail.

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Last Updated on March 12, 2023 by Leslie Livingston

The Perfect 2, 3 or 4 Days in Boston Itinerary

Last Updated on January 29, 2024

by Audrey Webster

Disclaimer: This article contains affiliate links. That means if you click a link and make a purchase, we may make a small commission. As an Amazon Associate we earn from qualifying purchases. For more information, see our privacy policy.

As one of the oldest cities in the country, Boston is filled with history. It’s a mash-up of cobblestoned streets and historic buildings with modern skyscrapers. There are a few places you cannot miss during a 2, 3, or 4 days in Boston itinerary, as well as some lesser-known parts of the city we’ll cover here.

As one of the most dynamic and historic cities in the country, there is a lot to do in Boston and so much that you can’t miss. From American history to esteemed universities to excellent museums and fantastic food (there’s more than clam chowder!), Boston has something to offer everyone.

Table of Contents

How Many Days in Boston?

When in the initial stages of planning a trip, many do wonder how many days to spend in Boston in order to do this New England city justice.

With 2 days in Boston, you’re just scratching the surface. Most of the city’s main attractions are clustered together, so you could see a lot in 2 days, but you’re also missing out on some cool parts that make the city unique.

If you have 3 days in Boston, you’re in good shape to see all the highlights as well as some lesser-known sites. You’ll be able to strike a balance between visiting historic landmarks and more trendy neighborhoods.

If you’re lucky enough to have 4 days, you can see more of the city at your leisure or use the fourth day to take a day trip to somewhere nearby. There is no shortage of historic sites and beautiful nature just outside Boston. 

Getting To & Around Boston 

You’re most likely arriving in Boston through the Logan International Airport. You can easily hail a cab, take the GO Boston Shuttle, pre-book a transfer or use public transportation to reach downtown.

If you’re visiting from another city or town in New England or even some city further south such as Washington DC or New York , you might arrive on a train or bus. Make sure to find out which train or bus transfers you need to make depending on where you’re coming from. You can view schedules here.

The Massachusetts capital is a very walkable city and it’s not actually that big. In fact, one of the best things to do in Boston is walk the Freedom Trail. Many of the most historic landmarks are located near each other.

Boston is also well-connected via a subway system, known locally as the T. You can easily get around the city using this if you want to reach somewhere a bit further afield.

Alternatively, there is the Hop On/Hop Off Trolley Tour that provides a convenient way to see the city. Taxis and rideshare are both readily available as well. It is also included in the Boston Go City Pass , which will also save you on entrance fees to many of the paid attractions listed here.

2, 3 or 4-Day Boston Itinerary

If you’re spending a few days in the Massachusetts capital, then there are a number of guided tours that you can take to get an overview of the city such as this historical walking tour , this bike tour or this food tour.

Day 1 – Freedom Trail, Museums, Quincy Market & More

Walk the freedom trail.

This 2.5-mile trail covers many of the historical highlights in Boston. You’ll want to dedicate a few solid hours to walking the trail. You can opt to walk the entire thing or a portion of it.

There are also guided tours available such as this 2-hour walking tour , which could be helpful for providing context to the landmarks as you pass them. Here are the landmarks you can expect to see:

• Boston Common & Boston Public Garden
• Massachusetts State House
• Park Street Church
• Granary Burying Grounds
• Boston Latin School/Benjamin Franklin Statue
• Old South Meeting House
• Old State House
• Faneuil Hall
• Site of the Boston Massacre

Paul Revere House

• Old North Church
• USS Constitution
• Bunker Hill Monument

You could spend however long you’d like walking the Freedom Trail and note that it doesn’t cost anything to walk the trail, but there are generally entrance fees for the various sites.

Depending on how long you want to spend, take the time to walk by these places and pick one or two that interest you to plan to visit those places. With that in mind, plan to spend 2-3 hours on the Freedom Trail.

Boston Tea Party & Ships Museum

Veer off Freedom Trail just slightly to pay a visit to the Boston Tea Party and Ships Museum.

The museum is chock-full with historical experts, interactive exhibits, full-scale replica sailing vessels, and historic artefacts to make this monumental event in America’s history come to life. You can pre-book tickets here.

If you have some time to spare, you can watch an award-winning documentary in Minutemen Theatre that depicts the events that led up to the American Revolution. 

Next to the museum, don’t miss the Observation Deck at Independence Wharf, either, where you can get excellent views of the harbor.

Quincy Market

Quincy Market is where old and new seamlessly merge. Here you can find hundreds of shops, both inside and outside the building. The market was established in 1825 and spans three buildings: Quincy Market, South Market, and North Market.

It’s another great place to stop as you’re walking the Freedom Trail to grab a bite to eat or do some souvenir shopping. The market is especially charming during the winter months when it’s decorated for the holidays. Quincy Market was named a National Historic Landmark in 1966. 

Go to a Red Sox game

Go see the “Green Monster” for yourself during your visit to Boston. Even those who wouldn’t consider themselves baseball fans will enjoy seeing a game at Fenway Park.

It’s been the home of the Boston Red Sox since 1912, making it the oldest stadium in Major League Baseball. If you don’t have time to see a game, you can still take a guided tour of Fenway. It’s a great way to wrap up your first day of sightseeing in Boston. 

If it’s not the season for baseball or you don’t care to go to a game, then use this time to stroll along the Charles River Esplanade or, perhaps, visit the nearby Boston Museum of Fine Arts. You could also simply relax in the tranquil surroundings of Back Bay Fens Park.

Day 2 – Boston’s Museums

John f. kennedy presidential museum & library .

This exceptional museum is dedicated to the life and accomplishments of U.S. President John F. Kennedy.

Here, you’ll wander the permanent exhibit that uses large-screen projections, interactive displays, original artefacts, and re-mastered films to learn more about the former president’s life. Consider reserving tickets online in advance to save you time at the door. You can also opt for a guided tour.

A visit to the JFK Presidential Museum & Library is a great way to kick off your second day. 

Institute of Contemporary Art

If you have 2 days, you should consider visiting one of the many local museums. A city that’s so full of history has some great historical museums, but it also has notable art museums like the Institute of Contemporary Art.

Here you’ll find both permanent and rotating exhibits featuring contemporary artists and their work. The museum is located in a beautiful building on the waterfront overlooking Boston Harbor, so you can also take in the view. It’s recommended that you book tickets in advance. 

Isabella Stewart Gardner Museum

This museum is known for its beautiful architecture and courtyard garden. It’s a great museum to visit if you want one that is a little less crowded than other larger museums in the city. Beginning in the late 1800s, Isabella started collecting rare books, manuscripts, and pieces of art to fill her home.

Over the course of her worldwide travels, she acquired art like Rembrandt’s Self Portrait and Titian’s Europa. The museum as it stands today was built in 1901. She lived on the fourth floor and spent the remainder of her life arranging the art throughout its halls.

It’s a unique museum that’s a quiet way to spend the afternoon. If this or any of the other museums don’t interest you, there are plenty of other museums in Boston to take in. For instance, the Museum of Science – located in a building overlooking the Charles River, is an excellent place to visit if you happen to be traveling with children.

Day 3 – Boston Common, Trinity Church, Paul Revere House & More

Boston common.

You might’ve already passed through Boston Common if you walked the entirety of the Freedom Trail. If you didn’t stop for long then, it’s worth your time to dedicate a couple hours to really enjoying the park. Boston Common is America’s oldest public park having been established in 1634 and is located in the Beacon Hill neighbourhood of Boston.

Today, the park is filled with fountains, picnic tables, and green spaces for visitors to lounge and enjoy the day. Make sure to stroll through the adjacent Public Garden, as well, to truly enjoy this urban green space. If you’re seeing Boston in 3 days, then a visit to Boston Common is a great idea.

Trinity Church

When you start exploring Boston, you’ll immediately notice Trinity Church in Copley Square. This historic stone church sits squarely in the middle of downtown’s towering skyscrapers. It’s considered by the American Association of Architects as one of the top 10 buildings in the country.

The parish located there today was founded in 1733, which is more than 150 years before the church was built in 1877. You can enter Trinity Church on your own or schedule a tour with a knowledgeable tour guide to learn more about the church’s history. 

It looks striking as it’s sandwiched between modern skyscrapers like the John Hancock Tower and the Prudential Tower and really symbolises Boston’s mingling of old and new.

Located in the North End neighborhood, the Paul Revere House was the former home of the famous Founding Father Paul Revere. He played a pivotal role in the American Revolution, noted in history books for his famous “midnight ride” to warn colonists that the British were approaching Boston.

The home was built in 1680 and is downtown Boston’s oldest building. Inside, the home is set up to mimic what it would have looked like while Revere lived there. In fact, 90% of the structure today is original material, including doors, windows, flooring, and internal wall material.

You can pop into this Boston museum for a self-guided tour or try to time your visit to see colonial reenactors demonstrate key moments of America’s history. 

If this doesn’t interest you as much or if you’re traveling with children, consider, as well, heading to the nearby New England Aquarium where you can learn all about local marine life or you can take a food tour of North End.

The Museum of Bad Art

You’ve probably never been to a museum that focuses on bad art. The Museum of Bad Art houses “art too bad to be ignored” and is a highlight worth adding to your time in Boston. It’s the world’s only museum dedicated to bad art that began in the basement of a private home.

The museum has since grown into a local favorite that shines the spotlight on quality bad art. It’s a quirky and fun addition to your Boston trip, especially if you happen to be planning a 3-day itinerary. 

Day 4 – Lexington & Concord, Salem or Cape Cod Day Trip

Lexington and concord.

Lexington and Concord is arguably the most famous site of the Revolutionary War. For history buffs, this is a great way to round out your 4 days in Boston. It’s where the first shots of the war were fired.

To reach Lexington, you’ll take the subway and bus for a total travel time of about 45 minutes before getting off at Lexington Battle Green. You can reach Concord by taking the MBTA directly from Boston.

Lexington Green is a good starting point for your visit. This small town is home to the Belfry that sounded the alarm in 1775 to call the militia to fight. Here, you’ll also find John Hancock’s childhood home or Buckman’s Tavern. In Concord, make sure you visit the Old North Bridge.

You can also find Walden Pond, made famous by writer Henry Thoreau, and Louisa May Alcott’s “Orchard House”. There’s a lot to see during a day trip to Lexington and Concord, so make sure you leave early in the day to give yourself ample time. 

You’ve most likely heard of Salem, Massachusetts due to its famous 1692 witch trials. Salem is only about 30 minutes from Boston, so it’s an easy day trip. You can easily reach it by taking the commuter train that connects the cities, a high-speed ferry or an organised day tour.

During your day in Salem, make sure to visit the Salem Witch Trials Memorial, Peabody Essex Museum, the Old Town Hall, and the Witch House. You can end your day with a visit to Winter Island Park and Lighthouse.

As you might’ve guessed, one of the best times of year to visit Salem is Halloween. The little town comes to life with spooky decorations.

Without a doubt, Cape Cod is beautiful, especially in summer. This stretch of coastline is full of charming towns, great seafood, and relaxing beaches.

Cape Cod is about 3 hours from Boston by car, which tends to be a little long for a day trip. Instead, you can take the Cape Cod Fast Ferry from Boston to Provincetown, which is the largest town on the Cape.

In Provincetown, you can enjoy the local art galleries, lounge on the beach, and walk around and enjoy the quaint homes and shops.

If you have more than 4 days in your Boston itinerary, spending more than one day on the Cape is a relaxing way to bring your time in the area to a close.

Where to Stay in Boston

Harborside Inn – This 3-star hotel in downtown Boston is a great choice for mid-range travelers to the Massachusetts capital. There are a number of great rooms to choose from, a wonderful location for exploring the city and plenty of other amenities to enjoy.

Omni Boston Hotel – If you’re looking for luxury while in Boston, then this sophisticated hotel is a great option. They have a range of lovely rooms on offer and an unbeatable location for exploring all this historic city has to offer.

HI Boston – Those visiting Boston on a budget will love this backpacker’s hostel in the center of the city. They have a range of both dorms and private rooms on offer along with other perks and great common areas for guests to enjoy.

Not quite what you’re looking for? Click here to browse more Boston hotels!

The perfect itinerary for Boston is the one that’s packed with what excites you most. If you’re a history buff, you’re going to love it here. Foodies, explorers, and everyone in between will find something to love in Boston.

Are you planning a trip to Boston? Have any questions about this itinerary? Let us know in the comments!

Related Posts:

The Perfect 2, 3 or 4 Days in Cape Cod Itinerary

Martha’s Vineyard vs Nantucket: Which Island to Visit?

17 Best Stops on a Boston to Bar Harbor Road Trip

About Audrey Webster

Audrey Webster is a writer for The World Was Here First. She is an Oregon native who has visited countries across the globe and currently spends her weekends exploring the Pacific Northwest and surrounding states. Her approach to traveling combines exploring famous tourist sites and wandering off the beaten path to discover new destinations.

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Home » North America » USA » 12 AMAZING Day Trips to Take From Boston!

12 AMAZING Day Trips to Take From Boston!

Boston is a fantastic destination that offers an incredible blend of old and new. But, it doesn’t stop at the city limits. Boston is within easy access of some of New England’s best destinations .

Once you’ve explored all that the city has to offer, you can set off for adventures to other nearby towns on day trips from Boston. Explore up and down the coast where you’ll discover quaint seaside villages, towns and historic settings of momentous events. The suburbs and towns on the fringe of the city are charming, welcoming and absolutely worth making time for during your visit.

If you’re exploring the city and are keen to venture a little further afield, this list of the best day trips in Boston will give you plenty to choose from, all within two and a half hours of the city!

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Getting Around Boston, and Beyond

Half-day trips from boston, full-day trips from boston, final thoughts.

The impressive city of Boston is easy to navigate , with plenty of ways to get where you need to be. Of course, like in most big cities, driving in the downtown area comes with challenges like the traffic and parking shortages.

• Most attractions in and around the city are easily accessed by public transport. Look for signs with a ‘T’ in a circle – these will take you to the subway which is great for getting to different parts of the city and surrounding suburbs. 
• A single one-way trip on the T costs around $2.75. 
• Consider buying a Charlie Card – a prepaid card for the subway. Load it with funds and top up as you need. 
• Boston is very walkable. Not only is it a beautiful city to stroll through, but most things are accessible within an hour’s walk. 
• Hop on a bicycle! The city has a great biking culture which makes it super easy to rent a bike and get around using pedal power. 
• Like most cities these days, there are a variety of taxi and rideshare options to use. These are handy especially if you’re out past the T’s operating hours. Services like Lyft and Uber are easy to access and use. 

For day trips from Boston, the bus is a reliable and affordable way to explore. The bus terminal is located on Atlantic Avenue – you may need to grab the T to get there from your hotel. 

Other options to get out and around exploring Boston include ferries and boat shuttles to other coastal towns and islands. 

If you find yourself with a morning or afternoon to spare, the areas surrounding the city are well worth exploring. Expect history in spades, quaint towns, and all the New England charm you can handle on these half-day trips from Boston. 

Half-day Trip to Salem

In 1692, Salem was the scene of infamous witch trials that have since inspired a thriving tourism industry. Just 30 minutes from the city, Salem is one of the most popular things to do in Boston . 

Options for witch trial related tours are abundant. There’s no shortage of guided, walking, and even self-guided tours through the turbulent history of this quaint seaside town. Take it up a notch on the thrill meter by opting for a night-time tour by lantern light – spookiness, guaranteed! 

But it’s not all about witches and spooks, Salem is a historical city with museums and monuments aplenty. From gorgeous, stately old homes to boat tours on the water, Salem has plenty to offer any visitor.

Suggested trips: Hauntings and History Walking Tour

Half-day Trip to Concord

Just 35 minutes from Boston by car, the city of Concord is a delight of Revolutionary War and literary history. Whether you choose to visit on your own or as part of a guided tour, there’s plenty to check out. 

Revolutionary War buffs should definitely check out the Minute Man National Historical Park, which includes the Paul Revere capture site as well as the option to walk along the Battle Road. You can wander around the vast park on your own, but we’d recommend doing a guided tour for a more insightful experience. 

The Concord Museum is relatively small but still interesting to visit. It won’t take you more than an hour or two to see all the original historic artefacts and exhibits from the town’s history. 

Concord has, over the years, been home to some literary greats whose homes you can visit while you’re in town. Louisa May Alcott’s Orchard House is a must-see for anyone who loved Little Women. Equally fascinating and well-preserved is Ralph Waldo Emerson’s house, as well as the Old Manse – a 19 th  Century house that was home to both Emmerson and Nathaniel Hawthorne. 

Don’t leave town without stopping by the Sleepy Hollow Cemetery. This beautiful leafy area is the final resting place of Thoreau, Emerson, Alcott, and Hawthorn, all within feet of each other in a spot called Author’s Ridge. Bonus points if you visit during the Autumn season when the trees turn all shades of red, yellow, and orange. 

Suggested trip: Private Excursion to Historic Concord

Sometimes after a full Boston itinerary , you want to get out of the city. Slightly further out are these Boston day trips will take you to Maine’s coastline and Rhode Island’s small towns. All within easy reach, these trips are worth checking out if you find yourself with a day to spare. 

Day Trip to Martha’s Vineyard

Just off the coast of Cape Cod, Martha’s Vineyard has long been the secret summer spot for the USA’s who’s-who. Anyone who’s anyone summers here on the reg, including the likes of Barack and Michelle Obama, David Letterman, and many other A-listers. 

For a day trip from Boston, Martha’s Vineyard offers a laid-back vibe, quaint coastal villages, and no fewer than five lighthouses ensuring safe passage for ships off the rocky coastline. 

You can spend your day on one of the incredible unspoiled beaches, relaxing away from busy city life. Definitely make time for some delicious seafood with a view of the boats on the water, and maybe a stop past the breathtaking Gay Head Cliffs. 

For something a little different, swing by the multi-colored gingerbread cottages in Oak Bluffs. This collection of cottages is like something out of a fairy tale and a must-see for the little ones. (Hint: visit in the summer when the houses are brightly lit in the sunshine and look eye-catching and festive.) 

Suggested trip: Martha’s Vineyard Day Trip from Boston

Day Trip to Portland

A drive two hours north of Boston will bring you to Portland, Maine, a popular foodie spot that really lives up to its reputation. Cuisine options include everything from Mediterranean fare to Vietnamese, and locally caught lobster to vegetarian delights. Whether you’re into fine dining or fusion food, you’ll not leave disappointed.

Blyth & Burrows is a favorite local spot serving killer cocktails artfully paired with small, tasty plates. 

Explore the quaint Old Port, with its hilly cobbled streets lined with boutiques, bars, and pubs. And if you’re keen to linger a little longer here (and we wouldn’t blame you if you did), choose to stay in a simple well located loft .

The Greater Portland area is home to the highest number of breweries per capita than any other city in the US. You can try everything from craft beers, stouts, and ales. There are also local wineries and distilleries.

If you’re the outdoorsy type, there are so many adventures to enjoy on a day trip in Boston. Think cycling, kayaking and paddleboarding, lobstering and fishing excursions, and even hover crafting on the bay.

Day Trip to Newport

Like most places in New England, Newport has a rich history stretching some 400 years. With water on all sides, it was originally the summer playground for the very well-to-do. Wealthy families built the now-famous Newport Mansion. 

Iconic and opulent grand homes have been perfectly preserved, some with art collections that would be the envy of any museum. If you’re a fan of HBO’s The Gilded Age, which was filmed in these very mansions in Newport, be sure not to miss out on this Boston day trip. 

The Breakers is just one of the more prominent of these grand estates and is conveniently close to the International Tennis Hall of Fame and the Audrain Auto Museum. There’s no shortage of historic homes, galleries, and museums in Newport to get a glimpse into day’s gone by. 

Visit one of the many picturesque lighthouses, and take in incredible views from the Cliff Walk. Fuel up at the White Horse Tavern – supposedly the oldest restaurant in America, or head down to Bowen’s Wharf where you’ll find a variety of restaurants and shops to explore. 

Suggested trip: From Boston to Newport Mansions Small-Group Day Trip

Day Trip to Provincetown

If you have the chance to visit P-town, take it! As the oldest continuous art colony in the country, Provincetown delivers charm and character in spadefuls. It’s also a favorite LGBTQ+ destination where absolutely everyone is welcome, and anything goes. 

Situated on a finger of land that juts into Cape Cod Bay, Provincetown is surrounded by water with plenty of beautiful beaches. Vibrant shops, galleries, and restaurants line the main street in town, and there’s usually an event or festival to check while you’re there. 

Provincetown isn’t an island, but it certainly has that kind of festive, laid-back vibe. In addition to whale-watching and hiking, the town is alive with art and entertainment, and food at any time of year. 

You can’t consider your visit here complete until you’ve climbed the Pilgrim Monument – a 252-foot granite tower that looks out over the harbor – or feasted on some freshly-caught seafood. Definitely try the Lobster Rolls – this town takes them seriously! 

Suggested trip: Cape Cod Fast Ferry

Day Trip to Providence

Providence is the kind of artsy place you can happily spend a day wandering round. It may be the capital of Rhode Island, but this city is charming and friendly and gives off major small-town vibes. 

If you’re into architecture, design, and art in general, then you’ll adore spending a day in the city checking out the downtown’s incredible buildings. See art deco, and beaux-arts buildings as well as gorgeous late Victorian terracotta-fronted gems. You can extend your stay in town and book a stay in a stunning downtown hotel originally built in 1929.

If looking at buildings doesn’t feed your soul, then the food scene in Providence certainly will. Each of the city’s vibrant neighborhoods has something to feast on, whether you’re looking for light nibbles, casual dining, or something truly decadent and over the top. 

Venture from the historic East Side to the West Side’s Federal Hill, which is home to over 100 restaurants and food markets – you’ll be feasting on everything from lobster to Italian! 

Day Trip to Plymouth

Even if you’re not American, there’s something special about standing on the exact spot where the first English pilgrims arrived in America 400 years ago. It’s this rich history that has consistently attracted visitors to Plymouth through the years, and makes this a popular Boston day trip. 

Visit the historic Plymouth Rock where the Mayflower came ashore, see the Pilgrim Hall Museum, and explore the meticulously preserved buildings like the Grist Mill or the Hedge House Museum.

But even if you’re not a history buff, Plymouth is a quaint destination with arguably some of the best whale watching to be had. Spend time in the beautiful outdoors at one of the many beaches, parks, and gardens, or take to the water in a kayak or boat.  

Stop in for a brew at the Mayflower Brewery or the Second Wind Brewing Company, or if wine’s more your thing, visit the Plymouth Bay Winery or the Uva Wine Bar to sample some of the local varieties. 

Suggested trip: Quincy, Plymouth, and Mayflower II Day Trip

Day Trip to Newburyport

Known to locals as ‘The Port’, Newburyport mounts a charm offensive on any visitors. Not only due to its scenic location on the coast where the Merrimack River meets the Atlantic, but because of its historic buildings in downtown. 

From the Cushing House Museum & Garden to the Custom House Maritime Museum, there are plenty of opportunities to discover local history. Otherwise, the waterfront area is great for a meander among the many restaurants and shops.

The major summertime attraction is by far the many excellent beaches. Nearby Plum Island is a popular retreat. A visit will include great beaches, an iconic lighthouse dating to 1898, and somewhere to enjoy a meal while watching the sunset at the Plum Island Grille. Check out this quaint little cottage if you want to extend your stay.

Sightseeing can be thirsty work, stop by one of the local breweries for a frosty craft beer. Try out the River Walk Brewing Company, the Newburyport Brewing Co., and House Bear Brewing. 

Day Trip to Mystic

Mystic is a quaint seaport village that fuses maritime history with that quintessential New England charm. From its iconic Bascule bridge to the old sea captain’s homes that line the streets, it’s easy to see why this picturesque town is so popular. 

Attractions here include the seaport, aquarium, and the Mystic Museum of Art. History lovers shouldn’t miss the Olde Mistick Village. A popular fall-time tradition is to visit BF Clyde’s Cider Mill – the only steam-powered cider mill in the US. Grab a cider and fresh donut before setting out to explore.

In the summer months, visitors usually head out on the water for a morning of sailing or a cruise. Whenever you visit, there’s likely to be some kind of celebration to check out!

Day Trip to Kennebunkport 

Kennebunkport is the kind of vacation destination that people return to time and again all year round.

Colony Beach and Goose Rock Beach are the two most popular spots. You can test out your sea legs on a boating adventure, like whale watching tours, lobstering tours, and other scenic sailing trips. 

After a day out in the sun, Dock Square is where you’ll find the town’s many restaurants to refuel. Grab a lobster roll at the Clam Shack or celebrate a special occasion at the town’s only five-star restaurant, The White Barn.

Stop in to see the historical artifacts collection at the Brick Store Museum and Nott House or visit the Seashore Trolley Museum – a must for train enthusiasts.

Suggested Trip: Kennebunkport Day Trip with Optional Lobster Tour

Day Trip to Lexington

In 1775, Lexington was the backdrop to a bloody battle between the patriotic Minute Men and the British army. The scene of the battle, Lexington Common, and its surrounding homes have been perfectly preserved, making it a popular Boston day trip for history lovers. 

In addition to the battle green, you can visit the historic Buckman Tavern (the oldest tavern in Lexington), The Old Belfry, the Old Burying Ground, and the Hancock-Clarke House for a step back in time. 

Visit the town center where you’ll find a variety of mom-and-pop shops to check out. Grab a crepe at Tres Petite Creperie, a fresh bagel from Wicked Bagel Bakery and Deli, or ice cream from local favorite Rancatore’s Ice Cream and Yogurt.

Visit the Lexington Arts and Craft Society or the Munroe Center for the Arts. Both offer exhibits by local artists as well as classes and workshops. 

Suggested trip: Battle Green Tour

Wanna know how to pack like a pro? Well for a start you need the right gear….

These are packing cubes for the globetrotters and compression sacks for the  real adventurers – these babies are a traveller’s best kept secret. They organise yo’ packing and minimise volume too so you can pack MORE.

Or, y’know… you can stick to just chucking it all in your backpack…

Don’t Forget Your Boston Travel Insurance

ALWAYS sort out your backpacker insurance before your trip. There’s plenty to choose from in that department, but a good place to start is Safety Wing .

They offer month-to-month payments, no lock-in contracts, and require absolutely no itineraries: that’s the exact kind of insurance long-term travellers and digital nomads need.

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Boston’s rich history and seaside location makes it a popular destination with tourists from all over the world. However, it’s not the kind of place you visit once and tick off your bucket list. It’s a destination that has much to give and many layers to explore.

The surrounding towns and cities of New England make for some truly memorable day trips from Boston. There are trips for foodies, history buffs, beer enthusiasts, and art lovers – truly something for everyone! 

You don’t need to be a history buff to appreciate a day trip to see Newport’s many mansions or spend a day (or night) on a witchy walking tour through Salem.

And for transparency’s sake, please know that some of the links in our content are affiliate links . That means that if you book your accommodation, buy your gear, or sort your insurance through our link, we earn a small commission (at no extra cost to you). That said, we only link to the gear we trust and never recommend services we don’t believe are up to scratch. Again, thank you!

Mary Beth Skylis

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The Perfect 2 days in Boston Itinerary

Last updated on March 20th, 2024

With a mix of history, city life, and delicious eats, Boston is a must-visit city in the United States. In this guide we’re sharing how to spend 2 days in Boston, including an itinerary, tips for visiting, where to stay, and more! For years we have dreamt of wandering around the Freedom Trail, eating some chowda, and watching the Red Sox in Boston. We finally made it happen and loved every second of our time in the city! Boston played an integral role in the founding of the United States, with many key events that led to the American Revolution. And the city is loaded with history around every corner. At times, it felt like we were just wandering around an outdoor museum!

Watch our experience in Boston , including part of the Freedom Trail, dumping tea into the sea, touring Fenway Park, and so much more!

But Boston has a lot more to offer than just history. It is a hotspot for Italian cuisine and seafood, home to the oldest MLB stadium in the US, has beautiful parks, cool neighborhoods, markets, and so much more. And with just 2 days in Boston, you can experience so much of what makes this city special! In this guide we’re sharing a Boston itinerary for 2 days, plus tons of helpful logistical information to help you plan your trip. We hope you love the city as much as we did!

This 2 days in Boston itinerary and guide is sponsored by Tripadvisor , the world’s largest travel website. On Tripadvisor you can not only read traveler reviews on hotels, restaurants, and activities, but there are also 300,000 bookable experiences, like food tours, museums, boat cruises, and so much more!  In this guide we’ll be linking to some of these Tripadvisor experiences, but as always, we’re sharing our honest opinions based on our personal experiences. Want 10% off a Tripadvisor experience? Use our code APLUSK10 !

Looking for more things to do in New England? 

• 12 Day New England Fall road trip itinerary
• 7 Day Vermont road trip itinerary
• Acadia National Park Itinerary
• Ultimate guide to driving the Kancamagus Highway in New Hampshire
• The BEST things to do in the White Mountains in New Hampshire
• Watch all of our New England adventures on YouTube

About this 2 days in Boston Itinerary

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Whether you have a weekend in Boston or are visiting on a weekday, this 2 days in Boston itinerary is perfect for first timers who want to experience Boston’s perfect mix of history, delicious local eats, and city life. We’re focusing this itinerary on things we personally experienced, plus spots that came highly recommended from friends and local followers. It’s a fast paced itinerary, but there are many ways to customize it for your interests or combine sites through tours.  We also are including a saveable Boston itinerary graphic at the end of this guide, so you can save an easy to read version to take with you on your trip!

Want to save some money while in Boston? If you book any of the tours or activities we’ve listed, or any other Tripadvisor experience around the world, use our code APLUSK10 for 10% off! 

The first day of this Boston itinerary focuses heavily on history! Today you’ll experience most of the famous Freedom Trail, try heavily debated Italian treats, and more!

Enjoy breakfast and coffee

Start your day with coffee and breakfast. You’ll need some fuel to conquer the big day ahead! Here are a handful of coffee and breakfast options in various parts of town, ranging from quick coffee shops to sit down restaurants.

Coffee shops in Boston

• Thinking Cup (they have multiple locations and we really enjoyed their coffee!)
• Ogawa Coffee
• The Well Coffee House
• George Howell Coffee
• Kohi Coffee Company
• Tradesman Coffee Shop and Lounge

Breakfast spots

• Tatte Bakery & Cafe
• Cafe Bonjour
• Capitol Coffee House (this is a hole in the wall, no frills spot with food served on paper plates)
• Mike & Patty’s High Street Place (get the breakfast sandwich!)

Want a unique breakfast experience? Go on an Underground Donut Tour where you’ll get to try multiple donut shops around town, while learning a bit about the city from a local guide!

Start your Freedom Trail exploring!

The Freedom Trail is a 2.5 mile (one way) pathway that connects 16 of Boston’s most historic and important sites . It is easily the most popular thing to do in Boston! If you follow this 2 days in Boston itinerary you will be visiting most of the sites. There are a few sites we are not including, but if you follow the Freedom Trail, you will go by them and can stop if you choose. We’re also mixing in a couple non Freedom Trail stops this day, as they are along the way and worth checking out!  The itinerary for day one may look like a lot of stops, but many of them are super quick. Also, if you decide to do one of the tours we’re linking below, your itinerary for day one will look a bit different, as you’ll visit most of these stops on your tour.

A few things to know before completing the Freedom Trail:

• Look for the red bricks on the ground! The Freedom Trail is marked by red bricks on the sidewalk. We didn’t know this during our visit and kind of just wandered around randomly. But for the best path, follow the red bricks!
• The National Park Service app offers a free audio tour of the Freedom Trail, Black Heritage Trail, Bunker Hill, and more! If you really want to dive in on the Freedom Trail sites, these free audio tours would be a good addition. 
• Most of the sites on the Freedom Trail have no admission fee, but some do. The Old South Meeting House, Old State House, Paul Revere House, and the Old North Church are managed by partner agencies and charge admission.
• Some of the sites you will just visit the outside and can access anytime of day, while others you may want to go inside. Make sure to check hours, as they can vary by day of the week.

For the best Freedom Trail experience, go on a Freedom Trail tour! While we explored on our own, going with a guide is truly the best way to learn Boston’s history. These guides are historical experts and can provide so much information that you may never learn on your own.  There are tons of options to choose from, but here are a handful that are highly rated. Bonus points if you choose one with a costumed guide! Entire Freedom Trail Tour : Want to experience the entire Freedom Trail with a guide? This tour is for you! On this 4 hour tour you will check out every single stop! The Revolutionary Story Walking Tour : This almost 4 hour tour will take you to many stops along the Freedom Trail. But instead of focusing on every site, they instead focus on telling the history of Boston, including tidbits not related to the Freedom Trail. Some guests on the tours are assigned characters! Freedom Trail Daily Walking Tour : If you have less time, this is a great shorter tour. And it is led by a costumed guide! You will explore the sites from Boston Common to Faneuil Hall, so there will be some stops to still check out on your own. Self Guided Audio Tour : Prefer to go at your own pace? This self guided audio tour will give you lots of historical information, but without an actual tour!

Granary Burying Ground

There are 16 historic burying grounds in Boston and the most visited is the Granary Burying Ground along the Freedom Trail. While there are only 2,300 markers, it is said that there are 5,000 people buried here, including Paul Revere and John Hancock, as well as victims of the Boston Massacre. During our visit, many tours were stopped here. The benefit of this is that we got to hear some fun facts, but we also had to battle some crowds to see the most popular gravesites.

King’s Chapel and Burying Ground

Just down the street from the Granary Burying Ground is King’s Chapel . This chapel was founded in 1686 as the first Anglican church in Boston. You can take a couple different tours inside ! Right next to the chapel is the King’s Chapel Burying Ground, which is said to be the oldest in Boston. While the burying ground is smaller than Granary, it’s a lot less busy and still worth a quick stop! What we found interesting as we wandered through different burying grounds is seeing how different the tombstones all are. And also seeing how many are extremely slanted!

Boston Latin School

The Boston Latin School was the first public school in America back in 1635. At the time, it offered free education to males of all income levels, with one student being Benjamin Franklin. The original schoolhouse is no longer there, but you can see a mosaic and statue of Benjamin Franklin to see where the school site was.

Old State House

Boston is the capital of Massachusetts. And the Old State House acted as the seat of colonial, and later state government, throughout the 1700s. There is a New State House just down the road, but the Old State House holds a lot of history! It was the site of the Boston Massacre in 1770, the first bloodshed of the American Revolution, and the Declaration of Independence was read for the first time in Boston from the balcony on July 18, 1776. You can view it from the outside, but if you’d like to go inside, admission is $15 for adults. Your admission also gets you into the Old South Meeting House , which is another Freedom Trail site and where the Boston Tea Party began!

Faneuil Hall

Faneuil Hall was the first public meeting space in Boston and a great stop along the Freedom Trail. It is ironically known as “The Cradle of Liberty,” despite Faneuil getting much of his wealth from human enslavement. Over its 280+ years it was home to many meetings, protests, and debates, as well as a marketplace. There are some exhibits on the first floor, which share some of the history of the hall. And you can go up to the second floor to see the Great Hall. Unfortunately during our visit, the Great Hall was not open. So make sure to check the hours here ! 

Visit a market

We love checking out markets when we travel. And Boston has several markets to visit, including both historic and new!

Quincy Market

Located right across from Faneuil Fall, the Quincy Market was built in 1826. Boston was rapidly growing and Faneuil Hall’s marketplace began overflowing with merchants. So they expanded just across the street!  Today, Quincy Market is a food hall and one of the most popular tourist spots in Boston. There are a variety of stands to get food from, plus some merchants selling souvenirs. We had heard it was pretty touristy and busy and while it wasn’t that busy for us (we went early on a Monday), it definitely felt touristy. We’d suggest walking through, just to experience its history, but we have another market that we suggest grabbing food at instead!

Boston Public Market

We had heard that Boston Public Market was a great alternative to Quincy Market. And we loved it! Boston Public Market is a newer market, opening in 2015, and focuses on New England food producers and artisans. Their mission includes supporting food growers and producers and cultivating a diverse community around food.  We really enjoyed the vibe of this market. It’s not huge, but it is really nice and has a good variety of vendors. Here you’ll find coffee, cider, pastries, seafood, flowers, produce, art, snacks, juices, a bar, and so much more! We grabbed a frozen coffee from George Howell Coffee , which was perfect for a muggy day. Plus a bowl at Mo’Rockin Fusion , a Moroccan spot, that was bursting with flavor! There were many other delicious looking spots and we hear that The Popover Lady is another must try. Since our next major stop involves food as well, we suggest grabbing a snack or splitting something so you have room for more food later!

Boston Haymarket

Just outside of the Boston Public Market is Haymarket , one of the nation’s oldest open-air markets, established in 1820. Here you’ll find tons of fresh, affordable produce, plus seafood.  However, it is only open on Fridays and Saturdays, so if you’re spending a weekend in Boston, make sure to check it out! It’s definitely on our list for next time!

Paul Revere’s House 

One of the most important historical figures in Boston is Paul Revere. He was a silversmith that is most famously known for his midnight ride at the start of the American Revolution. More on that in a bit! But while along the Freedom Trail, you can visit Paul Revere’s House , which is downtown Boston’s oldest remaining structure. You can view the house from the outside or pay to go inside and do a self guided tour ( prices vary ). Inside you’ll find a few rooms to explore, informational panels, plus museum interpreters to answer any questions. Just a heads up–photos are not allowed inside!

Eat Italian food in the North End

The North End is Boston’s oldest residential neighborhood and has been inhabited since the 1630s. In its early days it was occupied by 17th century Puritans and over the past four centuries, the area has been home to an African American community, and Irish, eastern European Jewish, and now more recently Italian immigrants.  By 1930, almost all residents were Italian. And because of this, there are many Italian restaurants, bakeries, and shops, even to this day!  You will naturally wander through the North End when visiting the next few Freedom Trail sights, so we suggest saving some room after your market exploring to enjoy an Italian lunch. Here are some must have food experiences!

Want to experience the best the North End has to offer? Go on a North End Walking Food Tour ! You’ll not only get to try some delicious Italian eats, but also learn the history of the area!

Cheap Italian eats

There are tons of Italian restaurants in Boston, from fine dining to grab and go. For lunch, we’d suggest doing something quick, as there is still a lot to see today! Plus, you need to save room for cannolis 😉. During our visit, we went to Galleria Umberto , a cheap, no frills, cash only spot. And we loved it! We got their Sicilian style pizza, which has a thicker, airy focaccia like dough or crust and is often baked in a pan so that the edges and bottom are a little crispy. It was delicious! We also got arancini, which is a deep fried, breaded rice ball with mozzarella, beef, and peas. It was hot, cheesy, and super comforting. Important note : this spot closes when it sells out, so arrive early! For other quick eats in the North End check out Monica’s Mercato , Dino’s Cafe , and Regina Pizzeria . Want something a bit fancier? We’re sharing more Italian options later on for dinner!

Try a cannoli (or two)

An iconic food item in the North End are cannolis. It’s a must-eat while in Boston! And there is a huge debate about who has the best. Below are three of the top contenders, ranked in order of popularity. Mike’s Pastry (Cash only) This is hands down the most popular spot. It has been around since 1946 and while some say it’s overrated, others say the crazy lines are for good reason. We lucked out and only had to wait a minute, but be prepared to spend some time in line here! Modern Pastry (Cash only) Started in 1930, Modern Pastry was founded by the Picariello family, who brought their recipes, culture, and hospitality from Italy. One unique thing about this spot is that they fill their cannolis when you order, so it’s a little fresher. You get to choose your shell, filling, and topping. Bova’s (Cash preferred) Another bakery in the North End that’s very popular is Bova’s Bakery. They’ve been around for nearly a century, offering Italian specialty cookies, cannolis, pastries, pies, sweet Italian bread, and more! 

So where did we go? During our visit, we tried the two most popular spots, Mike’s Pastry and Modern Pastry.  From Mike’s Pastry, we got the Florentine (we heard it was the best!), which has a shell made of nuts and honey. It was SO good, especially the shell! From Modern Pastry we got a plain shell, with ricotta filling and pistachios. It was also heavenly!  Since these were two different styles, we can’t fully compare them. But I think we both agreed we liked the Florentine shell better and the filling from Modern better. If the lines aren’t too crazy, grab a cannoli from multiple spots!

Old North Church

The Old North Church was built in 1723 and played a very important role in the American Revolution. Remember Paul Revere from a minute ago? This is where he began his famous midnight ride!  Paul Revere asked three Boston patriots to watch for British troop movement and hang lanterns in the Old North Church’s steeple to send a warning to the waiting American militia across the Charles River. Revere said to hang one lantern if the British troops marched by land and two lanterns if they approached by sea. Two lanterns were hung, and Paul Revere and others began the ride to Lexington and Concord to warn that the British were coming. The church is best viewed from the outside along Salem Street and you can purchase one of their tour options to visit inside. And as you walk to the church, make sure you stop at the statue of Paul Revere .

Copp’s Hill Burying Ground

The final burying ground along the Freedom Trail is the Copp’s Hill Burying Ground . This is Boston’s second oldest and is the final resting place of over 10,000 burials. One notable person buried here is Robert Newman, who is believed to be one of the two people who held a lantern in the steeple of the Old North Church. 

USS Constitution

Your final two Freedom Trail stops will take you across the Charles River to Charlestown! This is an easy walk from the North End, with a sidewalk along the North Washington Street Bridge or a pathway by the locks. Once over in Charlestown, make sure to head to the USS Constitution! This ship launched in 1797 and is the oldest commissioned warship afloat. It has sailed all over the world, including to the Caribbean, Mediterranean, Europe, the Pacific, and Africa. And has been involved in multiple battles, including the War of 1812, where it earned the nickname “Old Ironsides.” There are a few ways to experience the ship. You can view it from the Paul Revere Midnight Ride Landing Site , go inside the ship, or visit the neighboring museum.

Going inside the ship

The ship is owned and operated by the US Navy and is free to enter. However, it is only open Wednesday-Sunday from 10 AM-4 PM. Since we visited on a Monday and Tuesday, we were unable to do this, but it looks really cool! Note: Anyone 18+ must show ID to enter. So make sure you have it on you!

USS Constitution Museum

The USS Constitution Museum shares the history of the USS Constitution. It does not give you access to the boat, but is right by the boat. So if you’re visiting when the boat is open, you can easily combine them. The Museum is open daily from 9 AM-6 PM and is donation based, with the donation suggestions ranging from $5-$15 depending on your age. Tip: If visiting the museum is high up on your list, we’d suggest doing this on day two of this itinerary, so you don’t have to rush this experience!

USS Cassin Young

While at the USS Constitution make sure to visit the USS Cassin Young . It is free to enter!

Bunker Hill Monument

The final Freedom Trail stop is the Bunker Hill Monument . Back on June 17, 1775, this was the site of the first pitched battle between British troops and New England soldiers. On top of the hill is now a 221-foot tall obelisk built entirely of quarried granite, which took 17 years to build. You are able to go climb 294 stairs to the top to see Boston from above. And it’s free to do so!  The monument is closed on Mondays and Tuesdays and you can see its current hours here . This was another spot we had to admire from afar, due to visiting early in the week.

After a big, busy day of exploring Boston, end the day with a delicious dinner! There are tons of solid spots to choose from all around the city, but here are some options from a variety of cuisines! Italian: Carmelina’s , Giacomo’s , Mamma Maria , or Arya Trattoria Seafood: Warren Tavern ($1 oysters before 6 PM!) or Neptune Oyster Mexican: Tenoch Mediterranean: Oleana (a bit out of town!) If you want a drink, head to The Bell in Hand Tavern , the oldest continuously operated tavern in the US, Trillium Brewing Company , or visit the Samuel Adams Taproom !

The second day of this Boston itinerary focuses mostly on spots outside of the famous Freedom Trail. You’ll explore a beautiful park, eat more iconic Boston foods, check out a museum, and more! Since everyone’s interests vary, we’re including a handful of options today, so you can create your own perfect day!

Try a Boston Cream Pie 

While in Boston, you have to try a Boston Cream Pie! It’s the state dessert of Massachusetts after all! But despite its name, Boston Cream Pie is not actually pie, it’s cake. It’s layers of sponge cake, with a cream filling between them and chocolate ganache on top. And oh boy, is it GOOD! Boston Cream Pie was first created in 1856 at the Omni Parker House Hotel . And you can still eat it here today! At the bottom of the hotel there is a small shop where you can buy a Boston Cream Pie and other goodies.  However, for our Boston Cream Pie we went to Flour Bakery + Cafe and we highly recommend it. You may be thinking “cake for breakfast!?” Heck yeah! Rules don’t exist on vacation 😉. But the reason we suggest going to Flour Bakery + Cafe is because you can also get coffee and savory items to balance out the sweetness of the Boston Cream Pie. 

Check out a museum

Spend the rest of your morning checking out a museum! There are a bunch of great museums in Boston, but here are a few that we’d suggest during your 2 days in Boston!

Boston Tea Party Ships & Museum

One of the most iconic events to take place in Boston is the Boston Tea Party. This was a protest by American colonists in 1773 against British taxes on tea. While disguised as Native Americans, they dumped British tea into the Boston Harbor, showing their resistance to unjust taxation and British control. 

And the Boston Tea Party Ships & Museum is a great way to learn about the experience firsthand! During the tour you’ll be a part of a fun reenactment of the Boston Tea Party. The tour starts out with a town meeting, where you’ll get a character card (I had a speaking part!) and listen to your costumed leader. You’ll get riled up as you discuss the current taxation (fie!!!) and then go to the ship! Once on the ship, you get to see the inside, take an oath, and then throw tea overboard! For the last part, you’ll see an actual tea crate from the Boston Tea Party and watch a video about it.

And when you’re done, you can pay a bit extra to sample the five teas that were dumped into the harbor. It’s totally worth the cost! Make sure to try the strongest one. It’s smoky! Overall, we LOVED this experience! At the end of our 2 days in Boston, we agreed that it was easily one of our favorite things we did. It’s definitely touristy, but so much fun, especially if you really get into it. We embraced our roles and yelled huzzah as loud as we could! 

Book your tickets to the Boston Tea Party Ships & Museum on Tripadvisor! You can save 10% by using our code APLUSK10. Which if booking for two people, can buy you an extra cannoli! 

Isabella Stewart Gardner Museum

The Isabella Stewart Gardner Museum is an art museum tucked into what looks like a Venetian palace. It’s home to artwork that was collected by Isabella Stewart Gardner, a wealthy Bostonian, who passed away in 1924. When she died, her will states that the museum was not to change in any way. While this is still true and the museum is how she laid it out years ago, they have added a new wing, to better accommodate its high amount of visitors.  Something else interesting about this museum is that it was also home to the biggest art theft in history! Back in March 1990, two thieves dressed up as police officers and broke into the museum, stealing 13 works of art. Crazy!  We admittedly aren’t really art museum people, but this place does look amazing! Not only does it have tons of beautiful artwork, but the building itself is stunning and features both indoor and outdoor spaces. It feels a bit more like visiting a palace than a traditional art museum. Make sure to buy your tickets in advance . It does sell out! Note: the museum is not open on Tuesdays.

Museum of Fine Arts

The Museum of Fine Arts in Boston is a highly regarded art museum.There are 100 galleries of art and 500,000 pieces of work! Compared to the Isabella Stewart Gardner Museum, it’s more of a traditional art museum experience. But there are a ton of different styles of art to see, so there is something for everyone. You can get your tickets in advance , but it is not required, except for some exhibits. Note: the museum is closed on Tuesdays. If none of these museums appeal to you, you could also spend more time on the Freedom Trail, visiting the inside of some of the sights. There is no shortage of museums or interesting tours all around the city!

Have lobster and chowder for lunch

For lunch, grab two iconic New England food items: lobster and clam chowder! There are many places to eat both around town, but we went to James Hook & Co. , which has been family owned and operated since 1925. They have lobster in a few different ways and super creamy chowder! Another spot that came highly recommended is Boston Sail Loft . They also have some of the best chowder in the city and they add dill to theirs for a unique twist!

Wander through Boston Common and Public Garden

Boston Common is America’s oldest public park, established back in 1634! This park is technically on the Freedom Trail, but with so many other sights to see along the Freedom Trail on day one, we think it deserves more time than a quick stop! At the park you can find fountains, monuments, lots of green space, city views, and even a spray pool for kiddos in the summer. We enjoyed our walk through this park, but don’t just stop here. The neighboring Boston Public Garden is a MUST as well!

This garden has so many colorful flowers, a pond that you can take a swan boat ride on ($4.50 per adult), plus more monuments and statues. One of which being the Make Way for Ducklings statue , which is inspired by Robert McCloskey’s 1941 children’s book. This was a popular spot in the park for parents to get photos of their kids! Between parks you can also take a detour and wander around the charming Beacon Hill neighborhood!

Walking through Boston Common and Public Garden will lead you to the Back Bay neighborhood. This neighborhood is lined with gorgeous brownstone homes and you can find many local and brand name stores, plus tons of places to eat. It is also home to the finish line of the famous Boston Marathon. And on April 15, 2013, was where the Boston Marathon Bombing occurred. You can see two different memorials along Boylston Avenue, remembering the three lives lost that day.

Boston Public Library

Our favorite stop in Back Bay was the Boston Public Library . This library is STUNNING! You will feel like you just walked into an art museum. But it’s a library. And it’s 100% free to visit! The library has Renaissance style architecture, impressive columns, sculptures, paintings, and intricate details. There are various rooms to check out, plus an outdoor courtyard with a fountain. We were blown away by this place. It truly felt like we had been transported to a fancy museum or palace in Europe! We spend a lot of time at libraries while on the road. They are our go-to spot for a free place to work and this was easily our favorite library we have ever been to!

Tour Fenway park (& see a Red Sox game!)

Adam’s top bucket list item during our 2 days in Boston was to see Fenway Park. Home to the Boston Red Sox, this is the oldest MLB ballpark, built in 1912. And it’s a MUST see for baseball fans! During our visit we did the one hour Fenway Park Tour , where we got to walk all around the ballpark and learn tons of history and fun facts about Fenway and the Red Sox. Did you know Fenway is not symmetrical? Or that it has a rooftop farm? We also got to sit on the Green Monster, which was so cool! Our guide Joe was the best and even the lesser baseball fan of the two of us (Kathryn) really enjoyed it!

Book your Fenway Park Tour in advance to make sure you get a spot! Not a baseball fan? Check out a tour of Harvard or visit another museum instead!

Not only do we highly recommend the tour, but if you visit during baseball season (April to September), going to a game is a must! We were lucky enough to time our visit with a game and had such a fun night at Fenway. You can view the Red Sox schedule here .  We realize not everyone is a baseball fan, but just experiencing the energy and history of this place is a classic Boston experience! Tip: bags over a certain size are not allowed. We brought a small fanny pack and were fine, but if you have something much larger, you may have to store it nearby.

After another fun filled day in Boston, enjoy dinner in Back Bay! There are countless restaurants to experience in this area, but here are some suggestions to get you started:

Mediterranean: We LOVED Greco , which is a fast casual Greek Spot. For something fancier, check out Krasi , which is owned by the same people. Ramen: Hokkaido Ramen Santouka is a Japanese based chain with only a few US locations. And it’s said to be some of the best ramen in Boston! REDWHITE Ramen is another ramen spot in Back Bay with vegan ramen. Burgers: Boston Burger Company or The Capital Burger for a fancier burger experience. Can’t decide? Visit Time Out Market , a bit of a walk from Back Bay, to have a bunch of options all under one roof! Dessert : Amorino is a popular spot for dessert!

While 2 days in Boston is a great amount of time to get a taste of its history and delicious eats, there is a lot more to do in the city and surrounding area. If you have additional time or just want more ideas, check out these other things to do in Boston!

Go on a whale watching tour!

From May to October, whales migrate to the North Atlantic, which makes for great whale watching around Boston! We have gone whale watching in Hawaii and Alaska and it is a magical experience.

This half day whale watching tour is a great option! You will have the chance to see humpback and fin whales, plus dolphins. And amazing scenery along the way!

Visit the Samuel Adams Brewery

For the beer lovers, Samuel Adams is quite possibly the most famous brewer in the Boston area. While there is a taproom downtown, if you want to take a brewery tour , you’ll have to make a bit of a trek out to Jamaica Plain.

Want to visit multiple breweries? Check out this brewery tour , where you’ll get to visit 4 different ones!

Take a day trip

Boston is close to many other popular spots in Massachusetts, including:

• Cape Cod (~1.5-2.5 hours one way, depending on where you go)
• Martha’s Vineyard (ferry required)
• Salem (~40 minutes one way)
• Other historical destinations, like Plymouth (~1 hour one way)

These are all relatively easy to get to by vehicle, but will take at least a day to experience.

Don’t have access to a vehicle? There are a handful of day trips you can book with a guide, including Boston to Plymouth and Martha’s Vineyard .

Go on a Duck Tour

For a unique way to tour the city, go on a duck tour! Despite what younger Kathryn thought when she went on a duck tour in Austin, you are not on a tour to see ducks. Instead, you’re riding a “duck,” which is an amphibious vehicle that can drive on land and float on water!

This duck tour in Boston takes you by many of the Freedom Trail sights and on the Charles River!

Enjoy a sunset cruise!

Want to see Boston under the golden sunset light? Take a sunset cruise! There are a variety of tour options to choose from, depending on what type of boat you’d like to be on.

The Boston Harbor Historic Cruise and the Boston Harbor Sunset Cruise will both take you around Boston Harbor and near the USS Constitution. You can also cruise on a historic sailboat as well!

Hike Blue Hills Reservation

Hiking is our favorite activity and even being in a big city, there is nature nearby! If you’re looking for a bit of exercise and some views, check out the Blue Hills Reservation . It’s just under a 30 minute drive from Boston and has a variety of hikes to check out!

Get a Go City Pass

As you plan your Boston trip, you will likely see the Go City Pass . This pass gets you access to over 40 paid attractions in Boston, at discounted prices. It can be a good deal if you plan to visit a bunch of paid spots, but it depends on what your goals are during your trip. We suggest making a list of what you’d like to see, adding up the cost, and determining if this pass will be worth it to you. With us only having 2 days in Boston, it didn’t make sense. But it may be a good deal for you!

Boston, Massachusetts is located in New England, a region in the northeastern part of the United States. It is one of the major cities within the region, making travel to Boston pretty easy, with a variety of options.

Flying to Boston

The Boston Logan International Airport (BOS) is located only a 10-20 minute drive northeast of the main tourist areas of downtown Boston. As one of the major international airports in the US, it is serviced by just about any airline you would be flying in the US. One very neat feature about the airport is that it has a ferry terminal! You can take a ferry from the airport to Long Wharf right in the heart of Boston. This makes for a fun way to get to the city if the ferry’s schedule works with yours. You can also take the “T” (subway) from the airport.

Taking the train to Boston

If visiting Boston from a nearby major city on the East Coast, you can take a train into Boston! Amtrak’s Acela Train stops in Boston, as well as Washington DC, Philadelphia, and New York City. We personally love train travel! It may take longer than flying overall, but it tends to be more spacious and you can see more scenery. We would love to do this someday!

Driving to Boston

If road tripping around New England, Boston makes for a convenient stop. Here is how long you can expect to drive from nearby popular destinations!  Note: One thing to keep in mind when driving to New England is that many routes have tolls. If you want to avoid paying for tolls, make sure to turn off tolls on your Google Maps settings. We were able to get around New England by avoiding tolls and didn’t spend too much extra time driving.  Providence, Rhode Island: 1 hour, 15 minutes Newport, Rhode Island: 1.5 hours Hartford, Connecticut: 2.5 hours  New Haven, Connecticut: 2.5-3 hours  Portland, Maine: 3 hours New York City: 4-4.5 hours

Boston is a very walkable city. In fact, it’s said to be one of the most walkable in the US! We LOVED walking around Boston. It gave us the chance to see so much of the city, including many things we would’ve missed otherwise! Just make sure you wear good shoes, since you’ll likely walk a lot!

Public transportation

Boston also has one of the best public transportation systems , with subways, buses, and ferries. Depending on how long you’re staying and how much you plan to utilize the subways and buses, you can get a 7 day unlimited pass to cut costs! Our advice would be to utilize both walking and public transportation to get around Boston. 

Boston has a public bike sharing program called Bluebikes , where you can grab a bike at various spots around the city and ride around! For visitors, you can pay $2.95 for a 30 minute ride or $10 for up to two hours at a time for 24 hours. 

Similar to other large cities, there is also Lyft and Uber, so for any destinations that cannot be reached via the methods above, this is another option.

Do you need a car in Boston?

Unless you plan to do day trips to the surrounding area, you will not need a car in Boston. We’d actually advise against it, as paying for parking will add up and add an additional layer of complexity. So if you are heading off on a New England road trip after the city, rent a car at the end of your time in Boston. For our visit, we did not want to deal with our van in Boston, so we camped outside of the city and took the ferry every day. It worked out great!

The best month to visit Boston

Boston is a year round destination and the best time of year to visit depends on what you’re interested in, weather you prefer, and how many crowds you can handle. No matter what time of the year you visit, you’ll find a range of activities and attractions.  Spring in Boston offers milder temperatures, blooming flowers, and the city waking up after the winter. It’s finally pleasant enough to walk outside again and spend time at Boston Common and Public Garden. Baseball season kicks off in the spring and the Boston Marathon runs in April as well, so it is an exciting time to visit.

The summertime in Boston features hotel rates, temperatures, and crowds at their peak. It’s a great time for a Boston Red Sox game at Fenway Park, a boat tour in Boston Harbor, or a stroll along the Freedom Trail. Concerts and festivities will also be happening all around the city, so things are lively! Since summer is definitely the most popular time to visit, remember to pack your patience and know things will be busy.  For the most pleasant weather and, according to some, the most beautiful setting, plan your visit for the fall. The temperatures will likely be a little lower and the fall foliage will begin to show. This is when we hope to visit next time!  If you visit during the winter, you’ll likely see the city covered in snow and holiday decorations. You’ll likely notice less tourists too! Ice skating is a popular activity and if it gets too cold for you, you can always pop into a cafe, museum, or attend a theater performance. 

Day of the week

As for timing, we did notice that a lot of things were closed on Mondays and Tuesdays. So if your 2 days in Boston fall on those days, keep that in mind. However, it didn’t bother us, as we were fine seeing things from the outside.

Time of day

We also noticed that many of the sights on the Freedom Trail do not open until 10 AM or so. We’d suggest not starting your days too early, as you may have to hop around and backtrack. We tried to structure this Boston itinerary so that you’ll do things that are open earlier first! 

Boston has a handful of neighborhoods to stay in, each with its own advantages and unique characteristics. But, prepare yourself, staying in Boston is NOT cheap.  Below are some options in the most popular neighborhoods to stay in, plus a couple campgrounds for those in a van or RV like us. To see even more options, check out the best hotels in Boston on Tripadvisor . 

Downtown Boston is a bustling urban area and a great central location to base your stay. You’ll be close to many popular tourist spots, like Faneuil Hall Marketplace and Boston Common. Staying in the downtown area may be the most convenient, but you will pay for convenience.

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

Courtyard by Marriott Boston Downtown/North Station The Godfrey Hotel DoubleTree by Hilton Hotel Boston – Downtown

Vacation Rentals

Boston Fidi Studio King Bed Loft in the Heart of Downtown Downtown Luxury 1BR

Back Bay is a picturesque neighborhood lined with gorgeous brownstone homes, plus lots of shops and restaurants. It is a really neat area and centrally located to many of the popular sites in the city. We loved walking around here! 

Fairmont Copley Plaza Courtyard by Marriott Boston Copley Plaza Boston Park Plaza The Eliot Hotel The Verb The Revolution Hotel : This boutique hotel is not necessarily a hostel, although the rooms are private and many have shared bathrooms. They do also offer normal hotel style rooms! Oasis Guest House : This is a more affordable option located in brownstones. USA Today rated as “Best Value in Boston”

Great Back Bay Location Cozy, Adorable 1-bedroom apartment Elegant Back Bay Studio Airy Back Bay 2br/2bath Gem

Beacon Hill

Beacon Hill is one of Boston’s oldest and most picturesque neighborhoods. It has narrow cobblestone streets, gas lamps, and is overflowing with history and charm!

Prime Location | Beacon Hill & Financial District Convenient Beacon Hill 1BR Perfect Studio in Beacon Hill

Just across the Charles River, Cambridge is a great option if you’re planning on adding Harvard and MIT to your itinerary. Despite being away from the main tourist spots of Boston, Cambridge is still an easy public transport ride away. You can also save a little bit of money by staying out here!

Kimpton Marlowe Hotel Holiday Inn Express

Roomy 2BR in Kendall Square Lovely Kendall Square 1BR Hip East Cambridge 1BR near Lechmere T Station

One of the cheapest ways to visit Boston is by staying at a campground. Which is what we did! You won’t find campgrounds in the heart of the city, but if you don’t mind taking public transportation, it’s a great choice! We stayed at Wompatuck State Park during our visit and took the ferry into the city every day. Don’t let the $17 rate online fool you (it fooled us!), that’s only for Massachusetts residents. Non-residents can expect to pay $54-$60 per night. It’s a lot more than we normally pay, but is still much cheaper than a hotel in the city! It was a nice, wooded campground with cell service and hot showers. Some other options near Boston include Minute Man Campground , Normandy Farms Campground (we met some subscribers who were staying here and they loved it!), and Winter Island Park .

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Our Neighborhoods

A Perfect Weekend in Boston | Itinerary + Guide

By: Author Emily

Posted on Last updated: September 26, 2023

Up until recently, Boston was my favorite city that I’d never been to. Before I ever stepped foot in the city, I just had a feeling I’d love it there. We recently went to Boston for a long weekend, and I was pleased to have my suspicions confirmed. I loved it. If you too want to make your Boston dreams a reality, this is the post for you.

Follow along as we plan a perfect weekend trip to Boston, Massachusetts.

In This Post

• Getting to and Getting Around Boston

Where to Stay in Boston

• When to Go to Boston & How Long to Stay

Boston Weekend Itinerary

• Boston Walking Routes & Map

Other Things to do in Boston

How to get to boston.

If you’re coming from the Northeast, the train is a great option. We take Amtrak often and find that it’s usually on time and often very convenient. Amtrak has three routes with daily service to Boston.

• Northeast Regional: This train runs between Boston and Virginia. It makes stops in New Haven, New York City, Philadelphia, Washington DC, and many other cities along the way. The route separates near Alexandria and goes toward Roanoke or Norfolk.
• Acela: This train runs between Boston and Washington DC. It is a nicer train with Business and First Class only. It’s also a little faster and makes fewer stops than the Northeast Regional.
• Downeaster: This train runs between Boston and Brunswick, ME, stopping at 10 cities along the coast in between.

There are three Amtrak stations in Boston. The Northeast Regional and Acela trains stop at both South Station and Back Bay. South Station is the start of the line. If you’re traveling with a group in Coach on the Northeast Regional, I’d recommend traveling out of South Station. Since Coach is open seating, this gives you the best chance at finding seats together. The Downeaster trains stop at the North Station.

If you’re regional but not on a train line, driving is also an option. Boston isn’t the worst city to have a car. However, parking is expensive and not always available and/or complimentary at all hotels.

And finally, you can fly into Boston Logan International Airport if you’re coming from further away. There is no Metro station at the airport. Instead, there are frequent buses that run between the terminals and the Blue Line station. Even with the connection, this might still be the fastest option. Traffic around Boston Logan can be brutal.

Getting Around Boston

Boston has a decent Metro system that comprises both trains and trams, plus a wider web of bus routes. We found the trains and trams ran pretty frequently, but they didn’t have many cars and were often very crowded.

The Boston Metro does not have tap-to-pay gates. To board, you need to first purchase a ticket or transit card before you board. There are ticket kiosks at all stations. You can buy a one-way fare, load money onto a transit card (CharlieCard) or purchase an unlimited ride pass (CharlieTicket). Buses in Boston accept all of those ticket types, plus cash.

Central Boston is also pretty small (Fenway to the North End is only 3 miles). If you’re willing and able to walk, you can cover a lot of ground on foot. In fact, we often found that the Metro took just about as long as walking. The streets in Central Boston are a bit windy — we definitely missed Chicago’s grid system a few times. That makes them tricky to navigate, but it also means you can take slightly different routes each time.

The first thing to know when it comes to hotels in Boston is that they are expensive — and some are really expensive. Regardless of the season or day, it’s tough to find a hotel room for under $200 a night. Most hotels are going to be closer to the $250-$300 a night mark, with luxury hotels easily double that.

So once you’ve swallowed that pill, it’s time to pick your poison. Here’s a look at the best neighborhoods to stay in Boston and what hotels we recommend in each.

• Downtown: This is the business district, which is centrally located between Boston Common and the North End. It has the highest concentration of hotels. It’s busy during the week and pretty quiet on the weekend. We recommend The Langham (luxury) and Hyatt Centric Faneuil Hall (midrange).
• Back Bay: This upscale neighborhood is bustling all the time, particularly on nights and weekends. It has a great food scene and lots of shops nearby. It’s easily walkable to Fenway and Public Garden/Boston Common. We recommend The Lenox (luxury) and Courtyard Marriott Copley Square (midrange)
• Beacon Hill: This little pocket of town is charming as can be, but it’s a bit of a Metro desert. It’s not the best location for getting around to the rest of Boston. Stay here on your second visit when you plan to cozy up in Beacon Hill your whole stay. We recommend The Whitney Hotel (luxury) and Beacon Hill Hotel (midrange).
• Seaport: For a nautical New England vibe, head to this waterfront area on the south side of town. It is a bit trendier, has a lot of great views, and is close to its own set of activities. We recommend The Envoy Hotel, Autograph Collection (luxury) and Hyatt Place Seaport District (midrange).
• Fenway-Kenmroe: This is the area around Fenway Park. It is obviously a good pick if you’re just in town for a Red Sox game. There’s plenty of good restaurants and great parks nearby, too. We recommend The Verb Hotel or Residence Inn Back Bay/Fenway (both usually midrange, but expensive on game days).

We personally stayed in Downtown Boston at The Langham. The hotel was great, and it was a perfect location for our plans. The only thing we didn’t love was that several of the restaurants in the area were closed on weekends. Next time, I think we’d like to stay in Back Bay.

When to go to Boston

There’s a lot to consider when it comes to picking the best time to visit Boston.

First, there’s the weather. Boston has four distinct seasons with warm summers, cold winters, and consistent precipitation throughout the year. If you’re planning a lot of outdoor activities (like the Freedom Trail and parks), this matters a lot. We walked the Freedom Train when it was 85°F and sunny, and it was not fun. I assume it’s also not fun at 20°F.

The seasons also impact how the city looks and the activities that are available. In the fall, you might want to spend all of your time leaf peeping, taking colorful strolls through Public Garden and the esplanade. Christmastime will mean festive storefronts on Newbury Streets, Beacon Hill homes draped in garland and ice skating in Boston Common.

You also should plan for the specific things you want to do. Check the Red Sox schedule if you want to guarantee a game at Fenway. If you want to stay at a boutique hotel (like the Newbury Guesthouse), be sure to check their availability. Boston also has a handful of festivals you might want to plan around, like the Boston Seafood Festival in September or St. Anthony’s Feast in the North End in August.

Finally, think about the day(s) of the week you’ll be visiting and how that impacts your plans. For example, the business district downtown can be pretty dead on weekends and many restaurants are closed. If you do the Freedom Trail on a Sunday morning, you might not be able to go inside the churches. Tours of the Massachusetts State House are only available Monday – Friday.

So when is the best time to go to Boston? Personally, I’d recommend late spring (May-June) if you want to see a Red Sox game or peak fall (October) if you don’t care about baseball.

A visit to Fenway can really anchor a trip and is absolutely worth planning around. Late spring/early summer will give you the best shot at a game with good weather. Fall in Boston looks like an absolute dream. I planned a fall trip that we had to cancel last minute. Now that I’ve seen Boston in the summer, I’m even more confident that Boston in the fall would be perfect.

I would avoid summer if you are interested in the Freedom Trial, because the long outdoor walks are no fun in the heat. Christmas in Boston looks lovely, but any chance of snow can make travel plans flimsy and stressful. So for that reason, I’d avoid winter too.

How Long to Stay in Boston

A long weekend in Boston is pretty perfect. Ideally, you want to have at least two full days. If you have an extra half day on either of your travel days, that’s even better. That will give you just enough time to get a taste of the city and check off some of your must-dos. You won’t have time to do it all, but it’s a good excuse to plan another trip during a different season.

If this is your only trip to Boston in the foreseeable future and you want to get the most out of it, I’d suggest giving yourself at least 4 full days. With that much time, you could easily spend a day on the Freedom Trail, explore several different neighborhoods, make it to a Red Sox game (if in town) and visit a few museums.

In these next few sections, we’ll walk through our Boston weekend itinerary. We’ll narrate our specific experience, while also providing tips and recommendations based on what we learned. Before we get into the specifics, here are a few things to note about this itinerary.

We traveled from New York City to Boston on a Friday morning and left Monday morning. That gave us 2.5 days to explore the city. We were traveling with an almost-3-year-old, so our schedule includes nap times (most days) and early bed times. Our trip was in mid-July in the middle of a record heat wave and the Red Sox were in town. We stayed Downtown at The Langham.

And a final disclaimer, this itinerary calls for quite a bit of walking. Boston does have a Metro, but it didn’t always connect the places we needed to go. In many cases, the Metro was only a few minutes faster than walking, so we chose to walk.

Our NYC toddler is a great walker, so this worked out for us. If you are traveling with a child who can’t walk that far, be sure to bring a baby carrier or stroller. Strollers are generally fine around most of Boston, but they won’t fare as well on the cobble stones of Beacon Hill or the narrow sidewalks of Newberry Street. Instead, we highly recommend baby wearing for trips like this .

Without any further ado, let’s get this itinerary!

Arrival Day – Back Bay

We arrived in Boston by train around 1 PM and then made a quick 10-minute walk to our hotel (The Langham, Downtown Boston.) We checked in and our room was ready. They immediately sent housekeeping to our room to make up the sofa bed, so our toddler was napping shortly before 2 PM.

With a good 2-hour nap under our belt, we set off for Back Bay. We took the Green Line Metro (C or D lines work) to Hynes Convention Center Station, ready to walk Newbury Street from west to east.

Back Bay is a high-end shopping and dining district with several residential streets and office buildings mixed in. It’s a charming neighborhood with rows of brownstone homes, which give the area it’s distinctive look.

The heart of Back Bay is Newbury Street between Massachusetts Ave and Public Garden. The west end has more affordable shopping and the highest concentration of restaurants and the east end has the designer shopping.

I absolutely loved Back Bay. Unfortunately, our toddler was being a bit of a terror that day. (What is it about travel days that just turns children into gremlins?) We didn’t get to spend nearly as much time here as I would have liked, so it will definitely be on my itinerary next time we visit.

Things to see & do in Back Bay

• Newbury Comics: Their comic collection actually leaves much to be desired, but they have some great apparel, toys and gift-y items.
• Trident Booksellers & Cafe: Lovely bookstore, but I don’t recommend eating here when there are countless better options just down the street.
• Boston Public Library: This historical public library is free and open to the public. It’s a beautiful building that’s worth visiting even without a library card.
• Emack & Bolio’s : Yes, this is a chain, but it originated not far away in Brookline, MA so it still feels a bit local. It’s also delicious.
• Dirty Water Dough Company : Easy dinner option with outdoor seating and clever pizza combinations (including a vegan option).
• Buttermilk & Bourbon: Higher end dining option for southern food and seafood.
• Clarendon Street Playground: If you have kids, this is a good detour.
• Copley Square & Trinity Church : This entire area was under construction in summer 2023, but it’s worth noting for a future visit. Old South Church is also over here and very pretty.
• Commonwealth Ave Mall: If you’re making a loop through Back Bay, walk one direction down Newbury Street and the other down the mall. This walk would be extra pretty in the fall.
• Charles River Esplanade : This narrow park along the water has paved paths for running or walking, a playground, kayaking in the lagoon, and more. Great views, too.

Newbury Street ends at Public Garden, which borders Boston Common. Though not actually a part of Back Bay, these parks are a great place to relax before or after a stroll down Newbury Street. We walked through both on our way back to our hotel.

Day 1: Beacon Hill & Fenway

If you had one day in Boston, I would follow this itinerary to a T (plus maybe add a few things during the time we spent napping.) We strolled through the cutest neighborhood in town, explored a waterfront park, and then spent the evening at one of the most beloved baseball stadiums in the MLB.

Here’s how we spent our first full day in Boston.

Coffee & Breakfast at Tatte

Tatte (pronounced like “latte”) is a bakery and coffee shop chain in Massachusetts and Washington, DC. There are many locations in Boston, including in Beacon Hill. We personally went to the location closer to our hotel before heading to Beacon Hill, but you could do it either way.

What I love about Tatte is that you can just stop in for a quick coffee and pastry to go, or you can order a full restaurant-quality meal to eat there. It was the perfect place to enjoy a delicious breakfast without spending quite as much time as we would at a table-service restaurant.

The food was incredible. I had the most delicious halloumi breakfast sandwich, Kenny had the sweet french toast, and our toddler got the pancakes with the toppings on the side. The pancake order came with three giant pancakes, so we took two to our hotel and had breakfast for the next two days.

A Walk Through Beacon Hill

We walked from Downtown to Beacon Hill via Beacon Street to Joy Street to Mt. Vernon Street and on over to Charles Street. Taking a winding path through Beacon Hill is highly recommended.

I said Back Bay was charming, but Beacon Hill is somehow even cuter. Beacon Hill is exactly what I pictured Boston to be and it was perfect in every way. (It reminded me a lot of Gold Coast in Chicago, if you’ve been there.)

The neighborhood is one of the oldest in Boston and is largely residential. The streets (some of which are cobble stone) are windy and hilly, lined with federal style row houses and street lights that glow with real flames. The main shopping street — Charles Street — runs along the west side of the neighborhood and has a lovely collection of local shops and stores that feel so quintessentially New England.

Here are my favorite spots in Beacon Hill:

• Beacon Hill Cafe & Books: This book shop is great for people of all ages, but the kids section on the top floor is absolute perfection. There’s a little kid-sized door, a train that runs around the rooms, and lots of little chairs for your little reader. The cafe looks incredible, but reservations book up quickly, so we didn’t get the chance to try it.
• Gus & Ruby Letterpress: I love a card shop, and this one is perfect. They have cards, but also a great selection of little gifts, party supplies, colorful pens, etc.
• Whitney + Winston: If you have little ones in your life, you have to stop here. They have the most adorable clothes (pricey, though) and unique toys (my toddler was in love with the wooden barista set).
• East Coast Ivy Boutique: Don’t worry, adults have cute boutiques on Charles Street, too. The only thing people love more than the curated style is the kind salespeople.
• Mt. Vernon Street: This street is one of the most lovely in Beacon Hill, but honestly it’s worth strolling around all the residential streets over here. There are two other popular streets (Acorn Street and Louisburg Square), that are very beautiful but have signs that they’re private to residents. If you choose to venture down those streets, please be respectful.
• Blank Street Coffee: This is a chain coffee shop that’s all over, but I’ll take it over Starbucks any day. They have the best seasonal specialty drinks that always set the mood.

Charles River Esplanade

There’s a pedestrian bridge that connects Beacon Hill to the Charles River Esplanade. The esplanade is a large park along the banks of the Charles River that is cut in half by a narrow lagoon.

There are paved pathways around the entire park, so it’s popular with runners, bikers, and stroller parents. You can watch the boats sail past on the river side of the park or kayakers in the lagoon on the land side. There’s a playground and baseball diamond on the north end of the park, a small outdoor amphitheater, seasonal beer garden, and a splattering of monuments. The Charles River Esplanade also has several public bathrooms, which were clean in our experience.

We came to the esplanade for the playground. After a morning shopping in Beacon Hill, our toddler was due for some running around. The playground over here was nice, but it’s definitely targeted to bigger kids. (My kid is almost 3 and needed help with most things.) There was one big slide, but it was broken (it had a small hole on the side and was blocked off with a cone). The only way to get to the top of the slide was by climbing a web of nets, which wasn’t easy. There was also several spinning apparatus and a zip line.

The Charles River Esplanade was nice in the summer, but it looks like it would be extra lovely in the fall. Honestly, all of Boston looks like it would be lovely in the fall. (Okay, but also aren’t all places better in the fall? I digress.)

Lunch at Clover Food Lab

It was noon by the time we left the park and we were starving. We walked back toward downtown to get lunch because it was on the way to our hotel. There are lots of good options around here, but we chose Clover Food Lab.

Clover Food Lab is a quick-service vegetarian restaurant with several locations in Boston. It’s a good pick for vegetarians and/or coffee snobs. They have seasonal plant-based sandwiches, bowls and plates that are a nice and healthy alternative to the Impossible burger, salad or pasta option that typically checks the vegetarian box at most restaurants. Plus they have a curated coffee menu brewed primarily via pourover.

We walked from the Charles River Esplanade to the Clover Food Lab on School Street (near the Old Corner Bookstore on the Freedom Trail). It wasn’t a short walk walk (0.9 miles), but Google Maps said taking the Metro would only save us one minute. We were fine to enjoy the walk, most of which was through Public Garden and Boston Common.

We ordered the BBQ seitan sandwich, Impossible meatball sub and the peanut better/banana/honey sandwich for our kiddo. It was a bit expensive for what it was, but everything tasted delicious. We also got a blueberry lemonade and hibiscus tea, which were incredibly refreshing in the summer heat.

Our toddler can make it all day without a nap, but it’s not ideal. We only like to skip naps when we have to (which we’d end up doing the next day), and choose to take a nap break at the hotel today. I’d be lying if I said I didn’t also appreciate the 2-hour AC break in the middle of a long day.

My husband put our kid down for the nap and then went for a run in the hotel fitness center. I laid on the floor watching cooking shows on my phone and falling in and out of sleep. Same, same.

Red Sox Game at Fenway Park

We knew we wanted to plan our trip to Boston around a Red Sox game. As luck would have it, the New York Mets were playing at Fenway during one of the free weekends we had this summer. (We line in Queens and are Mets fans.) We happily planned our Boston trip around that.

The game was originally scheduled for 4 PM (pretty much perfect for our toddler who naps 1-3), but due to a rain delay it was pushed back to 7 PM (much less perfect for a toddler who goes to bed at 7.) We briefly considered skipping it, but decided it was worth a shot. We figured there was probably enough ice cream and popcorn to keep our kid distracted from the late bedtime.

It turned out okay and the game was absolutely incredible. As former Chicago locals who spent a lot of time at Wrigley Field, we were thrilled to get back to a real historical baseball field. The park was great and everyone was surprisingly nice to us — from the Red Sox dads behind us to the Mets fan next to us to the Fenway staff member who averted a near total meltdown by replacing our spilled popcorn.

We spent way too much money on good seats, but it was worth it. Our toddler could actually see the ball and the game being played, which kept them interested longer. Plus we had seats that were the front corner of a section, so our toddler could be trusted to sit or stand in their seat space without us worrying about them bothering fans next to or in front of them. It was truly a magical evening of baseball.

I have a detailed First Timer’s Guide to Fenway Park , but there are two things I will say in this post.

2 things to know about Fenway

• Get there early — like early, early. The gates open 90 minutes before the game, but crowds get there much sooner. We left at 4 PM for a 7 PM game and we had very little down time. After navigating the crowds on the Metro and at the stadium, taking a walk through the ballpark, and getting food, we were barely at our seats by game time.
• The Metro after the game is awful . The Green Line that stops near Fenway at Kenmore is not a proper metro train. It’s a tram with 2 cars. That is not enough for a stadium full of people. Plus, they didn’t seem to increase service to account for the crowds. It took forever, it was packed, and it was extremely unpleasant. (That’s coming from people who frequently crammed onto Red Line trains after Cubs games. It’s way worse than that.) Depending on how you feel about that, you will want to skip it entirely, leave before the game ends, or just be mentally prepared for it to suck.

Day 2 — The Freedom Trail

The Freedom Trail is a literal brick trail that leads past a series of historical sites around Boston. In full, the Freedom Trail is about 2.5 miles long and passes 16 sites. Most of the Freedom Trail is in the Downtown and North End neighborhoods, with the final few stops across the river in Charlestown.

If you want to visit all of the sites on the trail, go inside the sites that allow it, stop for meals, etc, the Freedom Trail will take an entire day. And even still, you might be hard-pressed to do it all and still make it to the final attraction (Bunker Hill Monument) before the inside portion closes at 4:30 PM. Doing the entire Freedom Trail in a single day is pretty exhausting.

Alternatively, we recommend a shortened version of the Freedom Trail. You can spend a half day on the Freedom Trail and finish up at Faneuil Hall for lunch. Another good options is to add a few more stops and finish at Old North Church in time for dinner in the North End. If you’re interested in the details of a shortened route, be sure to check out our Boston Freedom Trail in a Day | Guide + Map post.

If you take a shortened route that ends at either Faneuil Hall or Old North Church, you have more flexibility in your schedule to add in some unofficial Freedom Trail stops. The Sam Adams Taproom, Mike’s Pastry or even just a leisurely lunch somewhere are all great options that you might not otherwise have time for.

I wouldn’t feel bad missing the final few stops. The walk there is long and boring, and I would argue that these final two sites feel disjointed from the rest of the trail. If you do really want to see these final sites, I would do it on a different day. Not only will you have more time and energy to enjoy them (the Naval Yard alone can fill an entire morning), but you also won’t have to rush through everything else to get there.

But hindsight is 20/20. Here’s how we actually spent a full day on the Freedom Trail.

Freedom Trail (and more!) Walking Route & Timeline

Note: The (*) indicates stops that were along the trail, but not technically part of it.

• Boston Common (10:15 AM): We spent a half hour here, which included a stop at the playground and the small visitor center.
• Massachusetts State House (10:45 AM ): Tours are available, but we did not go inside.
• Park Street Church ( 10:50 AM ): We took a quick lap through the church, which has seen one too many restorations to be interesting.
• Granary Burying Ground (10:55 AM): We were offered a complimentary map which pointed us to the main grave sites. The large tour groups made this stop pretty awful.
• King’s Chapel (11:05 AM): You can usually go inside this church, but we caught it on a Sunday morning when it was closed to the public for service.
• Boston Latin School & Ben Franklin Statue (11:15 AM): The school is really just a mosaic monument and the statue is a statue. Quick and uneventful stop.
• Old Corner Bookstore (11:20 AM): The building still stands, but it’s no longer a bookstore. In fact, it’s a Chipotle restaurant. Another quick stop.
• Lunch break* (11:25 AM): We ate at said Chipotle and it was the worst Chipotle I’ve ever been to in my entire life. Just atrocious service, dirty store, and poorly made food. 0 out 10 recommend. Eat anywhere else in Boston.
• Old South Meeting House (12 PM): We bought a combo ticket to go inside this building and the next. The Old South Meeting House is one large room with a small museum exhibit along one side. They did have good, clean bathrooms downstairs.
• Old State House (12:15 PM): We used our joint ticket to go inside here, too. The museum portion was much bigger and well done, plus there was a gift shop (free to enter) and more clean bathrooms.
• Boston Massacre Site (12:30 PM): This is just a marker on the ground. Quick visit.
• Sam Adams Tap Room* (12:35 PM): We took a much needed break and enjoyed a beer (and a root beer) on the rooftop patio. The taproom is huge and the location across from Faneuil Hall is perfect. 10/10 recommend adding this to your route.
• Faneuil Hall (1:15 PM): This stop could take 5 minutes or 5 hours. There is Faneuil Hall Visitor Center which is mostly souvenir shops and then there is Faneuil Hall Marketplace which is massive and has a variety of restaurants and stores in and around it. We breezed through most of this, but would come back again.
• Paul Revere House (1:45 PM): I would have liked to go inside here, but the line was too long we were too hot and tired to wait in it. You can’t see much from the outside, so this was quick.
• Mike’s Pastry* (1:50 PM): This is a North End institution, so I was happy to wait the 20 minutes in line for a cannoli and slice of Boston creme pie. We ate our treats in the park by the Paul Revere Statue, which seemed to be the unofficial Mike’s Pastry seating area.
• Old North Church (2:40 PM): While Kenny got us some afternoon iced coffee, I took our toddler into the church. It was a $5 adult ticket, and kids 5 and under were free. The church itself was just okay, but they had a scavenger hunt for kids which mine loved . They got a sticker at the end for finishing it, and it was probably the highlight of the trip for them.
• Copp’s Hill Burying Ground (3:05 PM): We didn’t recognize any of the names of people buried here. We were so hot and tired by now that we just poked our heads in and carried on.
• USS Constitution (3:30 PM): We got to the Charlestown Naval Yard at 3:30 and immediately cooled off in the visitor center for a bit. The ship itself is free and was really cool, but we were just over it by now. You can also board the USS Cassin Young for free, which I popped into quickly while Kenny & Zoe relaxed in the shade. There’s also a museum, which we didn’t have time for.
• Bunker Hill Monument (4:40 PM): It was a hike to get here and a hike to get back to the train after and it wasn’t worth it. We didn’t want to go to the top, but it was closed even if we did.

After Bunker Hill, we walked 0.6 miles to the Orange Line stop at Community College Station. We took the train downtown and went back to our hotel. Instead of going out for dinner, we decided to go for a swim at the hotel pool and order room service.

If I sounded grumpy at the end, it’s because I was. It was just a really hot, really long day. The final stops just were not worth it for us. Looking back, we wish we would have just called it early and had dinner in the North End after the church.

Departure Day

Our train back to New York City departed South Station at 9:15 AM. We had a quick breakfast in our room and then walked to the station.

The Northeast Regional train starts in Boston at the South Station and then makes its first stop at the Back Bay station. Even if your hotel is closer to Back Bay, I’d still recommend traveling out of the South Station. This Amtrak train is open seating, so if you board at Back Bay, you might have a hard time finding seats together on a full train.

Otherwise, the train was very pleasant. It wasn’t quite as nice or as fast as the Acela, which we took too Boston, but it wasn’t bad. We snagged three seats in one of the few quads on the train, and it was perfect. (Oh! Also watch out for the Quiet Car, which is the second from the rear after the Business Class car. We accidentally sat there and had to move because our toddler definitely could not maintain a “library like atmosphere.”)

Boston Itinerary Walking Map

All of the walking routes in the itinerary above have been plotted out on the map below.

Before you dive in, here are a few quick tips for using this map.

• To view the map in Google Maps, click the expand icon on the top right corner.
• Click the star icon to save the map to your Google account for later. To access the map again, open Google Maps > click the Saved tab > click Maps.
• You can click the checkboxes beside each day’s walking route to add or remove those items from the map. This will help you see the map for one day at a time.

We easily filled 2.5 days in Boston, but left with a long list of things we still wanted to do. Here’s a peak at some other things to do in Boston that we didn’t cover here.

• Swan Boats at Public Garden: For under $5 a person, you can take a ride around the pond at Public Garden aboard the iconic swan boats. Boats run from mid-April to early September from 10 AM to 4 or 5 PM (varies by date).
• Boston Tea Party Ships & Museum : If you’re in Boston for history, this is probably a must-do for you. Tickets are pricy ($38 general admission) but include a 1-hour guided and interactive group tour.
• Boston Children’s Museum / Museum of Science: Both of these museums are good if you have kids and/or if the weather is bad.
• Eating & Drinking in the North End : The North End is Boston’s Little Italy. It’s filled with restaurants, bakeries and bars that are as tasty as they are historic. It’s a perfect place to end up after a Freedom Trail half day.
• Christopher Columbus Waterfront Park: We hardly saw the water at all during our Boston trip, and that’s wild to me! This park is beautiful and really gives New England harbor vibes.
• Back Bay Fens & Arnold Arboretum: If you’re visiting in the spring or fall and want to spend more time outside, both of these parks look stunning.
• Trillium Brewing Company: Drinking and Boston go hand in hand. If you’ve already checked off the Sam Adams Taproom and an Irish Pub, a brewery is next. Trillium is one of the best in Boston.
• Day trip to Salem, MA: It’s a quick 30 minute train ride to get from Boston to Salem. Most famously known for the Witch Trials and Hocus Pocus, this small town celebrates Halloween all year long (but mostly all of October.)

Closing Thoughts

I absolutely loved Boston. It had the conveniences of major city with the charm and walkability of a smaller New England town. (She says having been to no other New England towns). I loved exploring each of the different neighborhoods and re-learning a lot of the history. If you eat seafood, I can imagine you’d love Boston even more.

While Boston has a lot more to see and do, it’s still a great weekend destination for East Coast travelers. It’s easy to get to from around the region, which makes it appealing for repeat visits. We enjoyed our summer trip and going to Fenway, but I will absolutely prioritize fall for our next visit.

The Perfect 3 Days in Boston Itinerary (2024 Update)

• Last Updated: February 4, 2024

Planning a trip to Beantown and wondering what to do? Keep reading for an incredible 3 days in Boston itinerary!

Few cities are as important in the history of the United States as Boston. In fact, the capital of Massachusetts is known as the “Cradle of Liberty” for its role in the American Revolution.

Those interested in the early history of the USA will absolutely love visiting Boston. And you can cover some solid ground over a long weekend in the city.

In addition to all the historical sights, Boston boasts several world-class museums and some of the best universities in the world.

It’s also a top-notch sports city, with some of the most successful teams of all time like the Boston Red Sox, Boston Celtics and New England Patriots.

If you’re ready to plan a perfect vacation in Boston, read on for a solid gameplan for visiting this historic American city.

My epic itinerary will take you to:

READ MORE: Check out our brand new, complete guide on the best things to do in Boston !

Table of Contents

When to Visit Boston

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The first step in crafting a 3-day Boston itinerary is figuring out when to visit. Winters here can be brutally cold and unforgiving, which is not exactly ideal for exploring a city.

Of course, the warmer weather of the summer months also brings hordes of tourists and their selfie-sticks. For a nice happy medium, you may want to consider visiting Boston in late spring or early fall.

Whenever you visit Beantown, there’s sure to be a lot going on. In a city with so many major sports teams, art museums, and a lively music scene, you have tons of options for entertainment.

I don’t know about you, but I always check the calendar of events in a city before travelling there. If you’ve only got a few days in Boston, you might want to check and see if there are any games, concerts, or performances you’d like to attend.

Wherever you decide to lay your head during yours Boston itinerary, getting around the city is a breeze. Boston is a very walkable city and it also has excellent public transportation.

You can get most places in Boston on the metro, which is known as “the T” here. There are also local buses and ferries, as well as a commuter rail.

For visitors, your best bet is buying a CharlieTicket 1-day or 7-day pass. The 1-day costs $12.75 and the 7-day runs $22.50, so it’s actually a good deal even though you’re only spending a short time in the city.

Head here to read more about the various options for getting around Boston.

Read Next: Don’t forget to plan to enjoy some of the best Boston day trips !

Finally, the one thing I seriously recommend is investing in a Boston CityPASS , which is basically a card that gives you discounts at many of the main attractions in the city.

You buy the pass for $64, and it gives you entrance into the following Boston attractions:

• New England Aquarium,
• Boston Museum of Science
• Boston Harbor Cruise or
• Harvard Museum of Natural History
• Franklin Park Zoo

If you bought all of these separately, it’d cost $120.65, so you save 45% by buying the Boston CityPASS.

Now that you know a bit more about the city, let’s get this show on the road and take a look at what to do in Boston in 3 days.

Day 1 – Morning

If you want to start your day like a true Bostonian, grab a coffee and a donut from Dunkin’ Donuts and get a move on!

With a nice sugar high and a caffeine buzz, you’re primed and ready to kick off this itinerary.

When it comes to the best things to do in Boston, walking the Freedom Trail definitely tops the list.

This is a 4km-long path through downtown that takes you to 16 different historical sites, many of which played a role in the American Revolution. Follow the footsteps of the founding fathers as you take a walk through American history on the trail.

The best place to start out is Boston Common, which is actually the oldest public park in the country.

You’ll have to save chilling in the park for later, though, as we’ve got a busy Boston itinerary to get to!

Heading north out of the park, you’ll visit several important historical landmarks on the North End.

There’s the Massachusetts State House, King’s Chapel Burial Ground, the Old South Meeting House, and Old State House, among others.

The latter is the site of the Boston Massacre, which served as a catalyst for the Revolutionary War.

Following the Freedom Trail through the North End on your own is quite easy, as it’s well-marked and there are plenty of informative signs along the way.

You don’t have to join a guided tour. If you’re on a budget, you can just make your own tour.

Click here to download the official brochure of the Freedom Trail and then head here to check out an interactive map.

Those who prefer listening to reading can drop down a cool $15 to download a 2-hour audio tour . Just download the app and purchase the tour and you’re ready to rock.

Finally, you can sign up for an official tour and have a knowledgable local guide lead you around town.

READ NEXT: Looking for more history? Be sure to check out our list of the best things to see and do in Philadelphia !

Day 1 – Afternoon

How long you spend on the Freedom Trail is entirely up to you. Most of the sites are free to visit, but a few of them charge an entrance fee (Old State House, Old South Meeting House, and Paul Revere House).

Some people like to linger and read all the information, while others prefer to breeze through and snap a photo or two. Personally, we spent about three hours visiting a bulk of the sites along the way.

After taking in so much history in so little time, you’re probably ready to chill and grab some food. Thankfully there’s a spot on the trail that makes for the perfect lunch break.

READ MORE: Check out our other epic city guide on how to spend 3 days in New York !

With only a few days in Boston, you’ll definitely want to try as much local food as possible. Hopefully, you’re nice and hungry by this point in the day, because there are lots of options at Faneuil Hall on the edge of North End.

This is one of the most historic sites in all of Boston, as it’s where the Sons of Liberty gathered to discuss independence from Great Britain. It’s been an important meeting place and market ever since it was built in 1742.

To learn more about the importance of Faneuil Hall, you can join a free talk in the historic Great Hall. These begin every half an hour between 9:30 and 4:30.

Oh yeah, back to the food! Sorry folks – there’s just so much to cover with only so much time! Inside the hall, you’ll see lots of excellent options in Quincy Market.

When in Boston, one must eat a bowl of chowdah . For those unfamiliar with the Boston accent, I’m talking about clam chowder – a creamy seafood soup that’s a local favorite.

Or splurge and get a classic New England lobster roll!

If you want to be a mega-tourist, add a stop at Cheers. This bar is a replica of the one from the famous TV show and while a bit cheesy, is a fun place to grab a drink.

Before you go, be sure to check out the amazing street performers outside of the hall. From magicians to jugglers to clowns to mimes, there are some incredibly talented people here.

If you’re feeling the history vibe, then you can keep on cruising along the Freedom Trail and cross over the Charles River.

You could easily spend the rest of your afternoon crossing the remaining sites off your list, among them Paul Revere’s House and the USS Constitution.

Both charge an entrance fee ($5 and $10 respectively) so you may want to take that into consideration.

Should you feel a bit tired of reading plaques and looking at statues, just head back to where the day started and spend some more time exploring Boston Common.

Take a walk through the park and cross Charles Street, and you’ll find yourself in the Boston Public Garden. Cruising around the pond on a swan boat in Boston Public Garden is definitely among the top things to do in any Boston itinerary.

Near Boston Public Gardens and Boston Common is Beacon Hill , another gem of the city. Beacon Hill is one of the most beautiful Boston neighborhoods, so if you have time time it’s worth strolling around.

Beacon Hill is a residential area full of picturesque brick buildings, old fashioned apartments, and lots of greenery. Beacon Hill is always charming, but it is especially scenic if you visit in winter when there is snow falling everywhere.

Read Next: Looking for more history on the east coast? Check out our awesome 3 days in Philadelphia itinerary !

Day 1 – Evening

After a very busy start to your Boston itinerary, it’s time to enjoy a bit of leisure time to wrap up day one. And I know just the place to do that!

Once you’re satisfied with your time in the garden, head out to nearby Newbury Street. This popular commercial area is famous for its well-preserved brownstones that house a wide variety of businesses.

Unless you’re looking to drain your wallet, move quickly along the street. You see, the higher end of the street is full of luxury brands, earning it a reputation as one of the most expensive streets in the US.

As you get to the lower numbers, you’ll find some more budget-friendly options. Take your pick from the countless cafes, shops, and bars here before our last stop.

To wind down day one, head to the nearby Skywalk Observatory for the best panoramic views of Boston.

The observatory is located atop the Prudential Centre and it’s the only sky-high vantage point in the city. Try to time your visit around sunset for an absolutely epic view!

Tickets are a bit pricey at $21 for adults, but it’s worth it on a clear day. You can even see into the neighbouring state of New Hampshire on a nice day here.

In addition to the observatory, your ticket also includes admission to the Dreams of Freedom Museum. This museum celebrates the diversity of Boston and the importance of immigrants in shaping the city.

If you’re looking for a nightcap, there are plenty of bars in the area. Otherwise, head home and get some rest to gear up for the remainder of your time in Boston.

Day 2 – Morning

Rise and shine, because we’ve got another big day in Boston! Grab some brekky and coffee, lace up your walking shoes, and let’s go!

Thanks to its location, Boston has a beautiful waterfront with plenty to see and do, particularly on the North End. This makes for the perfect place to spend a relaxing morning in Beantown.

The thing about the Waterfront is that there’s just so much going on here that there’s no way to pack it all into your Boston itinerary. That’s why it’s time to…

While I’m here to help you explore Boston in 3 days, I’m not giving you a concrete Boston itinerary. Travel is all about going with the flow, after all. That’s why it’s time to choose your own adventure at this point in the tour!

Here are just a few of the many things you can do along the Waterfront:

This beautiful green space offers some fantastic views of Boston Harbor on the North End. On a nice day in Boston, there are few places better to be than this!

In addition to enjoying the views, you can also take a walk in the rose garden or head across the street for a ride on the Greenway Carousel.

Another option while you’re over here is the New England Aquarium. It’s a very impressive aquarium, highlighted by their Giant Ocean Tank. This is home to the aquarium’s most famous resident – Myrtle the Sea Turtle.

You can also catch a show at the IMAX theatre or join a whale watching tour here. These tours run between April and November and make for an unforgettable experience.

Click here to buy an entry ticket to the New England Aquarium. Unless you already have a Boston CityPASS, in which case the ticket is included!

HOT TIP: The New England Aquarium is included with your Boston CityPASS!

In the Waterfront area, you have plenty of options for a unique guided tour of Boston. Take your pick between an Old Town Trolley Tour , a Boston Harbor Cruise, or a Duck Tour.

If you’re wondering about that last one, I’m not talking about exploring Boston with a flock of birds.

A “duck” is a special amphibious vehicle that brings you on a tour of Boston before splashing down into the Charles River.

A Duck Tour is a super family friendly way to explore Boston by road and by water.

Alternatively, you can book a Boston Harbor cruise . Boat cruises are always fun, and there is a wide variety of boat tours in Boston to choose from.

Choose between a historical sightseeing cruise , a Boston Harbor Cruise with buffet lunch , or a sunset yacht cruise.

You can also tour Harvard University , one of the country’s most famous schools. The grounds are beautiful and lots of cool history happened at Harvard University, so it’s worth checking out.

Day 2 – Afternoon

Whatever you decide to do on the Waterfront, make sure to include a quick stroll along the scenic Rose Kennedy Greenway.

This is one of the best places for cafes and restaurants in the area, so go ahead and take your pick for a lunch break.

There are several great museums to choose from in Boston, and a few of them are located right over here.

If you’re ready to dive back into the history lesson we started on day one, head to the Boston Tea Party Museum & Ships. Here you get to go aboard a replica ship and actually re-enact the famous event.

The Boston Tea Party is one of the most well-known events in American history so it’s kind of like meeting a celebrity.

Tickets for the museum cost $40 for adults and you can save a few bucks by booking online . This is a rare museum that’s fun for the whole family, so it’s a great choice if travelling with kids.

Speaking of the kiddos, the Boston Children’s Museum is located right next door. It’s an interactive museum and is super fun, even for big kids! Tickets cost $18 and you can book online .

While Ben Franklin may not have ever actually uttered the words “Beer is proof that God loves us and wants us to be happy,” there’s still a lot of wisdom behind the quote!

It’s been a busy time in Boston so far, so I’d say it’s time for a cheeky brew!

Cruise over to the nearby Seaport District of Boston to find Harpoon Brewery & Beer Hall. They run tours every day and tickets are sold on a first-come, first-serve basis. Check their website for all the details.

If you just want a drink and don’t need a brewery tour to go along with it, another option is the Fort Point location for Trillium Brewing . These guys make some killer beers and have a solid restaurant as well.

While it’s a bit of a hike from the harbor, Samuel Adams is probably the most famous Boston brewery.

They’re located in the Jamaica Plain part of the city and their last tour starts at 5 PM. Check their website to read about all their tour options.

Day 2 – Evening

How you choose to spend your evening totally depends on what time of year you visit, your interests, and your energy level. After all, it’s already been a huge experience in Boston so far!

With so many options and so many variables, you know what that means. It’s time to choose your own adventure.

As a native Detroiter I hate to admit it, but Boston is one of the best cities for sports. Not just in the US, either, but in the entire world.

I mean, they won the Super Bowl AND the World Series in the same year and were just one game away from adding the Stanley Cup. That’s unreal!

If you’re in Boston between October and May, there’s a good chance either the Celtics (NBA) or Bruins (NHL) have a home game at TD Garden.

Even if they’re away, the bars around the arena are lively. I particularly enjoyed the hilariously named “The Greatest Bar.” Yeah, they’re not too humble around here when it comes to sports and drinking!

While the New England Patriots (NFL) are technically a Boston team, they play pretty far outside of the city centre. If you’re willing to make the trek, most home games are on Sunday afternoons between September and January.

If the Red Sox are in town, you should definitely try to score tickets. After all, baseball is America’s pastime! Plus, the Red Sox play at Fenway Park, the oldest ballpark in the country.

Historic Fenway Park has to be on your list of what to see in Boston, even if there’s no game going on.

You can book a 1-hour guided tour of the sports ground here .

Live music lovers will be happy to hear that there are plenty of options for jamming out in Beantown. From a classy night out with the symphony to a wild night of head-banging along to some heavy metal, you can find it here.

To figure out where to go for some tunes in Boston, I recommend checking out this article on the 25 best music venues in the city. I always use Jambase to see what shows are on in a city when I’m travelling there.

Of course, you can always just go out and see where the night takes you. This is a city that likes to party so you’re guaranteed to find something fun. You’ve got to go big at least one night!

Day 3 – Morning

Depending on how your night wound up, it might be a slow start to the final day. Thankfully there’s no shortage of places to get a late and leisurely brunch in this town!

We hit up Zaftigs Delicatessen ( click here for directions) during our Boston itinerary and really enjoyed it. There’s nothing like some eggs benedict and a strong coffee to bring you back to life!

Let’s finish up this itinerary with a bang!

To kick off day three, head to the Fenway-Kenmore part of the city. Here are some of the best museums in town, including the Museum of Fine Arts Boston , which dates back to the 19th century.

You could honestly spend the entire day in here and not even scratch the surface. They have such a vast collection of art from all over the world it’s mind-boggling.

Be sure to have a look at their visitor guide so you can make a gameplan. Tickets cost $25 for adults and you can book online ahead of time to skip the line.

Another one of the best art museums is the nearby Isabella Stewart Gardner Museum . This incredible art museum is located in the former home of its namesake, which was built in the style of a 15-century Venetian palace.

Inside, you’ll see three floors full of art, surrounding a lovely courtyard and garden. This has got to be one of the nicest looking museums out there!

At just $15, the Isabella Stewart Gardner Museum is well worth the price of admission to add this one-of-a-kind museum to your itinerary.

Click here to book tickets online.

Another option is the Institute of Contemporary Art . Located on the waterfront, this stunning museum showcases so much interesting contemporary art and often has performances and exhibitions. Visit the website for more info!

HOT TIP: The Museum of Science is included with your Boston CityPASS!

Whichever museum you choose to visit, be sure to drop by the nearby Back Bay Fens on your way out. This tranquil green space is a part of the larger Emerald Necklace chain of parks throughout Boston and Brookline.

This is the perfect place for a leisurely stroll after a jampacked 3 days in Boston. While you’re here, don’t miss the beautiful Kelleher Rose Garden.

In addition, you can visit one of only two remaining “Victory Gardens” in the US that were planted by citizens to help grow food during World War II.

There’s also a temple bell here that was donated by Japan after the war as a symbol of peace.

Day 3 – Afternoon

After a moment of peace and quiet out in nature, it’s time to finish up your Boston itinerary! Next up, we’re headed to one of the most iconic places in the city – Fenway Park.

Since it’s a major sporting venue, there are tons of places to eat and drink around Fenway. Go ahead and take this opportunity to grab some lunch and take a load off before visiting the ballpark.

Dating back to 1912, Fenway is the oldest ballpark in America. It’s home to the city’s beloved Red Sox, and is a must-see when you visit Boston.

As I mentioned earlier, it’s worth it to visit Fenway even if there isn’t a Boston Red Sox game going on. They run tours of the ballpark from 9-5 during the season, even on game days (tours run 10-5 from November to March).

In an age of excessive corporate sponsorship and tacky theme park-esque ballparks, it’s nice to visit one of the originals. I’m a Tigers fan for life but I’ve got to admit that going to Fenway Park is an incredible experience.

On a tour of Fenway, you’ll get to learn all about the unique features of the ballpark, such as its famous “Green Monster.”

You need to book ahead of time if you want to do a tour, and you can do that here .

If there’s not a game going on at Fenway or you’re just not into baseball, let me present an alternative option.

Not too far up the road is the John F. Kennedy National Historic Site, birthplace and childhood home of the 35th US President.

You can normally tour the grounds, but the National Historic Site is actually closed until 2023 for maintenance and renovations. But when they are ready to reopen, it should definitley have a place on your Boston itinerary. Check their website for more information.

If you’d like to learn more about JFK and his legacy, you can also consider adding a trip to his presidential library and museum to your Boston itinerary.

Day 3 – Evening

Congratulations on making it to the end of a busy stay in Boston! I definitely didn’t go easy on you with this one…

If you actually followed this beast of an itinerary, chances are you’re pretty spent by now. It’s your last night in Beantown, though, so power through and head out for one last night.

With so many options in Boston, it’s time once again to…

We’ve already covered sports and live music here, but there are lots of other great options for entertainment in Boston.

One popular option is an escape room. There are a few near Boston Common, including Trapology and Escape the Room . Find the clues and solve some mind-bending puzzles to make your escape in time!

Perhaps you’d rather wind down your time in Boston with some laughs. The city is home to many excellent comedy clubs, including Improv Asylum.

Check out their website to see what’s playing while you’re in town.

If you’d prefer to just have a nice dinner and a few drinks, the area around the Waterfront is full of great restaurants and bars.

South Boston, locally known as “Southie”, also has great nightlife.

And that about does it for how to spend 3 days in Boston!

Boston Travel Guide

Where to stay in boston.

This isn’t the biggest city, but you still want to give some consideration to where you stay. Downtown is the hub of tourist activity and thus has the biggest selection of accommodation.

If you’re planning on spending a lot of your time in Boston in museums and at the ballpark, the Fenway-Kenmore area is a better choice. Those focused on fine dining and shopping should look to the Back Bay area of the city.

Beacon Hill is centrally located, but it’s quite expensive.

In these areas, you’ll find a wide range of accommodation choices.

Boston is home to budget hostels, mid-range hotels, luxury resorts, and everything in between. Here’s a top choice for each category:

When it comes to hostels, you just can’t beat HI Boston. It’s in a great location, just steps away from Boston Common and the start of the Freedom Trail.

Hosteling International is all over the world and they know what backpackers like! They offer free breakfast as well as free walking tours, a nice TV room to chill in, a pool table, and much more.

HI Boston also has laundry facilities and a nice cafe with free WiFi if you need to get a bit of work done or just post pictures from your awesome 3 days in Boston.

Dorm beds here are comfy and each one has a light and outlet. These range from $40-60 a night depending on the number of beds in the room.

This fantastic hotel is located in one of Boston’s most historic neighbourhoods – Back Bay. Here you can see 19th-century townhouses.

They have four different room types, from their standard room to their luxury bay window king room. All rooms include free WiFi and breakfast.

All guests can enjoy their nice common area, where there is a computer and printer along with free tea, coffee, and cookies. Yummy!

If you’re hoping to catch a game at Fenway, this is an excellent choice as the ballpark is just a mile away. Rooms start at $259 a night here.

If you’re looking to live it up, the Boston Waterfront Hotel on the North End is the place for you. This 5-star hotel is located right on the Rowes Wharf and is known for its “classically current” style.

All of the 232 rooms here are beautifully designed with tremendous attention to detail. These range from their Superior Room all the way up to the unreal John Adams Presidential Suite.

There are several options for wining and dining on-site, including the Meritage Restaurant & Wine Bar and Brewer’s Alley. You can also get room service here 24/7!

As if that weren’t enough, they also have a state-of-the-art gym here with a three-lane pool and a spa. You’re really living the good life if you stay here!

DISCLAIMER: Some of the links in this article are affiliate links, which means if you book accommodation, tours or buy a product, we will receive a small commission at no extra cost to you. These commissions help us keep creating more free travel content to help people plan their holidays and adventures. We only recommend the best accommodations, tours and products that ourselves or our fantastic editorial team have personally experienced, and regularly review these. Thanks for your support, kind friend!

Sasha and Rachel

Hi, We’re Alesha and Jarryd!

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I would love to visit Boston in the summer! This itinerary looks perfect!

This is an excellent itinerary for anyone planning a short trip to Boston! Your suggestions for must-visit sights and activities are well thought out and cover a good range of interests, from history to food to outdoor exploration.

Thank you so much. We appreciate it 🙂

Great 3 days itinerary!Really useful tips about and informative content about boston.Thanks for sharing.

Thanks so much. Glad the article was helpful. 🙂

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Adventures in New England

A local's guide to savoring the history, culture, food and nature of the Northeast USA

19 Fabulous Day Trips from Boston

If you are planning a road trip from southern New England, Boston can be a perfect base as it is centrally located. You can get a hotel and then take many great day trips from Boston to experience the best that this area has to offer.

You will want to start by taking a few days to experience New England’s largest city’s feel. You can read my guide for One Day in Boston with Kids (still a good overview even for adults). Also, be sure to check out my list of hikes right around Boston .

Table of Contents

Short Day Trips from Boston

These day trips from Boston are around an hour’s drive from Boston.

Salem, Massachusetts

Witch City, USA, also has a fantastic art museum and Hawthorne’s House of the Seven Gables. Read on for how to spend a day in Salem. 

Fall River and New Bedford, Massachusetts

This center of fishing life in colonial New England is now predominately Portuguese. You can visit the New Bedford Whaling Museum, the church that was part of Herman Melville’s Moby-Dick inspiration, and the Lizzie Bordon House.  Read more about the area in Haunted New England.

Rockport, Massachusetts

Spend a day exploring this picture-perfect fishing village on the coast north of Boston.

Cape Cod, Massachusetts

There is a lot to explore on this peninsula south of Boston, but you can explore the upper Cape in one day from Boston. Most of my exploration of the Cape has been by bicycle.

Portland, Maine

This foodie town also has lighthouses and parks to explore. Check out 47 Cool Things to Do in Portland, Maine.

Providence, Rhode Island

The capital of Rhode Island has canals to stroll along, great restaurants, and art museums. Read on for The Best Things to Do in Providence.

Newport, Rhode Island

This colonial town on Aquidneck Island has excellent beaches, hiking, dining, and a lot of history. Explore A Local’s Guide to Newport.

Sutton, Massachusetts

Hike this trail along the base of the 75-foot rock Purgatory Chasm and get ice cream at the farm next door. Read more about a day at Purgatory Chasm.

Concord, Massachusetts

Concord was not only an important location in the American Revolution but also in American Literature. Walden Pond sits in Concord, as well as Louisa May Walcott’s home. Read my itinerary for one day in Concord, Massachusetts.

Plymouth, Massachusetts

Visit the recreation of the Native American and pilgrim colony following the landing at Plymouth Rock.

New Bedford, Massachusetts

Explore the colonial whaling capital of the world, located on the southern coast of Massachusetts. This area also has a large Portuguese population, a fort, and was a stop on the Underground Railroad.

Read about how to spend a day in New Bedford. 

Whole Day Trips from Boston

It will take about 2 hours to get to these full-day trips from Boston.

Martha’s Vineyard

Sand dunes, farms, Kennedy history, and gingerbread cottages, this island off the coast of Massachusetts will introduce you to the best New England has to offer. Read on for Things to Do in Martha’s Vineyard .

Woodstock, Vermont

Woodstock is sometimes known as the quintessential New England town. It is nestled in Vermont’s Green Mountains and alive with the state’s art culture. Plan your day with Things to Do in Woodstock, Vermont.

Northampton, Massachusetts

This arty town in northwest Massachusetts is the home of Smith College. Read on for how to spend a day in Northampton.

The Berkshires, Massachusetts

One of the most transcendent concerts you can experience will take place at Tanglewood in the rural mountains of western Massachusett. The Berkshires give ample opportunities for hiking, leaf-peeping, and exploring small New England towns.

New Hampshire’s White Mountains

Take a foliage drive or go waterfall hunting through the White Mountains.

Mystic, Connecticut

Explore the seaport at this colonial town on the Mystic River. Investigate more things to do in Mystic.

Mount Major, New Hampshire

The views from the peak of this half-day hike are incredible. You will see New Hampshire’s lakes and highest peak, Mount Washington, in the distance. Learn more about climbing Mount Major.

Shelburne Falls, Massachusetts

This village nestled in the Berkshire Mountains has the Bridge of Flowers, a waterfall, glacial potholes and an art-filled downtown. Read about how to spend a full day in Shelburne Falls.

Which day trips around Boston have you taken? Which are the highest on your list? Please let me know if you have any questions in the comments.

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12 thoughts on “19 Fabulous Day Trips from Boston”

I love this list! Boston is such a cool city and I love the idea of spending more time there and venturing out so this list is so helpful!

So many great day trip options from this city! Nice when there is that option, for travellers, it means you can extend your holiday. Make Boston your home base and see some of those smaller towns you have listed. I would love to see more of the nature, in New Hampshire, like Mount Major or Massachusetts with Martha’s Vineyard.

Such great day trip plans even a month of stay there will not suffice to experience it all! The short day trips really sound good and doable. I have not been to Boston yet, but hopefully I will some day with this helpful post! Great pic to go with the post.

Wow! So many things to do. It would really be worthwhile to make Boston a base for a week and do these trips to immerse yourself in the region.

Visiting the east coast has always been something i’ve wanted to do. I’ve seen Boston & DC but that’s about it! Rhode Island, Connecticut, Vermont, Main, I want to see them all!

Funny enough I’ve heard most of these day trips destinations from Boston although I don’t know their locations to Boston. I would like to visit most of them, but I think Fall be the best time?

Some of the locations are close enough for a day trip but would plan an early start in the day because even though they are close enough for a day trip, traffic can play a big factor especially during rush hours… planning a trip to the South Shore or Cape Cod offers only 2 travel lanes for most of the trip once you are on Route 3 which starts in Braintree which is about 9 miles south of Boston and the from Braintree to the beginning of the cape it’s about 45 miles or so… I mention this trip because I am very familiar with this section of MA and I live in Plymouth which is about 10 miles from Cape Cod… The Fall or Spring would be best as far as traffic to the cape but many places close down from Oct to Apr because many businesses depend on tourists during the Summer.

You are right about Boston traffic being a bugger. It is always best to consult Google traffic before leaving, start early or consider public transport. I love travelling in shoulder season.

While there’s still so much to see and do on my actual Boston list, I *did* take a day trip from Boston during one of my visits. We followed your recommendation to visit Providence, RI, and had a lovely day!

I just love the northeast and you’ve given me even more places to explore up there! Perfect fall long weekends!!!

Cape Cod, Massachusetts would be my #1 choice. Haven’t been since I was little and have such fond memories!

I have been to Boston several times now and even took a trip up to Maine & Connecticut once but I have been quite lax on visiting the other areas. For me, I really want to see more of the New England Coastal areas like Providence and I know Darcee would love to see Martha’s Vineyard!

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Boston Travel Guide

Looking for something fun to do in Boston, MA? We are here to help you decide what to do on your visit. Find your next great experience on our Calendar of Events . It provides the most popular Boston events , concerts , theater shows , musicals , sports events , festivals, holiday happenings, family events, unique tours, and more. Let us help you plan your vacation and discover everything Boston, MA has to offer. From tours and restaurants to things to do , get the most from your trip!

Best Events

Upcoming Events & Tickets

Best Boston Tours

5 Top-Rated Tours from Boston, MA

Discover the best Boston tours. Explore 100+ points of interest. Hop on and hop off at all popular Boston tours and attractions. We’ve got several options to choose from to help you maximize your time in Boston and still see the best first. See our most recommended things to do in Boston, MA.

Boston Hop-On Hop-Off Trolley Tour with 15 Stops

Explore the best that Boston has to offer on this hop-on hop-off tour of the city. See Boston’s top attractions—like the USS‘Constitution’ and the Boston Tea Party Ships and Museum, to name a few—on the loop. Enjoy discounted admission to attractions like the Boston Tea Party Ships and Museum with the purchase of your tour. If you upgrade to the Gold or Platinum Pass, you will be given your (seasonal) Harbor Cruise ticket when you check in for the Trolley Tour. These seasonal cruises depart periodically throughout the day close to Stop 1.

• Discover Boston at your leisure with a hop-on hop-off trolley tour.
• See the most popular sights of Boston at your own pace.
• Hop on and off at any of the stops as often as you wish.

Martha's Vineyard Daytrip from Boston with Round-Trip Ferry & Island Tour Option

Overview Join Boston’s only award-winning, original, Martha’s Vineyard Day Trip! Leave the trouble of driving to someone else and enjoy a day trip to Martha’s Vineyard from Boston. Then, take a short cruise to Martha’s Vineyard then enjoy free time to explore or upgrade to add an island tour. Complimentary snacks, bottled water, island guidebooks, and a discount card with island perks are provided during the drive.

• Hassle-free ride from Boston to Cape Cod aboard an air-conditioned Mini Coach Bus
• Panoramic ocean views on a cruise between Cape Cod and Martha’s Vineyard
• Spend hours exploring Martha’s Vineyard at your leisure – beaches, shopping, and dining available.
• Narrated Island Tour upgrade available with stops in Edgartown and Gay Head Cliffs

Boston Tea Party Ships & Museum Admission

Relive the most important event leading up to the American Revolution on this self-guided tour of the Boston Tea Party Ships and Museum. Take a journey back in time to the famous Boston Tea Party, an incident that changed the course of American history. It’s more than a stroll through historic artifacts, though. It’s truly one of the top-rated museums in the city of Boston. Explore authentically restored tea ships and throw the fated tea into Boston Harbor.

• Admission to the Boston Tea Party Ships and Museum.
• Get an in-depth look at the events leading up to the Boston Tea Party.
• Learn how the Boston Tea Party kick-started the American Revolution.
• See one of the two remaining tea chests from the Boston Tea Party.

Boston Historic Sightseeing Harbor Cruise with Up-Close View of USS Constitution

See some of the top attractions in Boston from the waterfront on this narrated sightseeing cruise. Explore Boston Harbor and see the city’s historic sites while listening to live commentary on board. Pass landmarks like the Boston Tea Party ships, USS Constitution, and Boston Light—the oldest continuously manned lighthouse in the United States.

• Historic sightseeing cruise of Boston Harbor.
• Narrated tour with tales of the Revolutionary War, Legends of the Sea, and Boston’s Historical Figures
• See America’s oldest continuously manned lighthouse
• Sail through the Harbor Islands National Park Area and Boston’s working Port.

Boston Whale Watching Cruise by High-Speed Catamaran

Experience the best of New England’s marine wildlife on this guided whale-watching cruise around the Stellwagen Bank National Marine Sanctuary. Hop on a high-speed catamaran that gets to and from the whales in the least amount of time possible. See humpback and fin whales, plus Atlantic white-sided dolphins with the help of a naturalist guide. The onboard galley offers food and beverages for purchase during the trip.

• Boston Whale Watch Cruise aboard a high-speed catamaran.
• See Humpbacks, Finbacks, and the critically endangered Right Whales during your sail.
• Enjoy a scenic whale-watching cruise around Stellwagen Bank National Marine Sanctuary.
• Narrated by a New England Aquarium Naturalist as your Guide.

Boston Day Trips

5 Top-Rated Day Trips from Boston, MA

Blessed with beautiful natural areas, Massachusetts contains an array of unique attractions for all types of travelers. In cities and towns, visitors will find museums, unique attractions, and great restaurants. In the more remote parts of Massachusetts, there are waterfalls, miles of hiking trails, and tranquil beaches. Classic New England towns and quiet fishing villages line the Massachusetts coast. Massachusetts enjoys a unique history that lives on in full force through its special attractions and well-preserved historic places.

Martha's Vineyard Day Trip with Optional Island Tour from Boston

Visit Martha’s Vineyard on a day trip from Boston to experience the island beauty without the hassle of booking ground and ferry transport. From hotel pickup and drop-off to included ferry tickets, snacks, water, and sightseeing maps, this Martha’s Vineyard excursion is designed for maximum time exploring, with the option to upgrade and include a guided tour of the entire island aboard a high-top, small-group van and explore all six towns on the island, indulge in lunch, and spend more time learning about scenic New England.

• Ground and boat transport get you to the Vineyard with one booking.
• Customizable tour: choose between independent and guided options.
• Early departure for more time on Martha’s Vineyard.
• Ferry trip is a great chance to see the coast and marine wildlife.

Boston to Salem One-Way or Round-Trip High Speed Ferry

Don’t let time determine whether to see Boston or Salem. Visit both towns with the help of a quick and comfortable catamaran. This high-speed ferry service travels from Boston to Salem (or vice versa). Enjoy the scenic adventure from the upper or lower deck of the boat—or just relax at the lounge inside. An onboard galley offers food and beverages for purchase. Upon arrival, many top attractions are within walking distance. One-way or round-trip tickets are available with a variety of convenient departure times.

• Fast, efficient transportation between Boston and Salem.
• Onboard galley offers food and beverages for purchase.
• See top Salem and Boston attractions within walking distance of the ports.
• One-way or round-trip ferry service available.

Boston to Plymouth Day-Trip including Quincy, Plimoth Patuxet and Mayflower II

Discover historic New England as you explore two iconic Massachusetts destinations on this full-day tour from Boston. Travel through Quincy, MA, the birthplace of two U.S. Presidents, and journey along the state’s South Shore coastal area on route to Plymouth. Explore the 400-year-old town’s harbor, enjoy lunch (own expense), view Plymouth Rock, and tour Plimoth Plantation. You’ll also board the Mayflower II and learn the fascinating history of the Pilgrim’s.

• Explore multiple historic New England sites in just one day—ideal for travelers short on time.
• Bypass lengthy queues with skip-the-line entrance to Plimoth Plantation.
• Admission to the Mayflower II included as an added convenience.
• Round-trip transport by mini-coach ensures a stress-free excursion.

Boston to Newport Small-Group Day Trip with Breakers & Marble House Admission

Escape the hustle of the city and get away to the tranquility of Newport, Rhode Island, on a guided, small-group day tour from Boston. This quaint coastal town, known as America’s First Resort, is the perfect getaway and just 70 miles south of Beantown.

Explore the Breakers mansion, the most grandiose of Newport’s summer mansions. Visit attractions like the Ocean Drive Historic District, the St Mary’s Church complex, and the U.S. Naval War College, among others. Hotel pickup and drop-off plus a snack, guidebook, and discount offer card are included.

Boston Freedom Trail Day Trip from New York City

Swap the Big Apple for a day in history-steeped Boston undistracted by transportation worries. Travel to the city by comfortable vehicle, and enjoy a comprehensive tour of its highlights with the benefit of a guide for commentary. Stroll around Cambridge’s Harvard Yard, admire the city’s Revolutionary-era landmarks along the Freedom Trail, and enjoy free time for a lunch of local favorites such as clam chowder at Quincy Market.

• Explore historical Boston on a day trip from New York City.
• No planning needed: go by luxe vehicle and hear about the sites via a guide.
• Tour Harvard, walk the Freedom Trail, and see the Boston Tea Party site.
• Time for local seafood meal (own cost) such as lobster roll at Quincy Market.

Welcome to Boston, MA

Boston , officially the City of Boston , is the capital and most populous city of the Commonwealth of Massachusetts in the United States and the 24th-most populous city in the country. Whether you’re a local, new in town, or just cruising through we’ve got loads of great tips and events. Boston is perfect for family fun and romantic getaways. Start planning your Boston trip. Explore the complete list of Entertainment Venues in Boston , MA. Check out our events calendar for concerts , theater shows , musicals , sporting events , and more.

Entertainment Venues

14+ Day Trips in Massachusetts With Kids

I t’s a small state, but my home state of Massachusetts is filled with family-friendly activities. From the historic attractions in Boston and Plymouth to the beaches on Cape Cod and the Islands, there’s so much to do. Whether you are visiting Massachusetts on its own, or as a part of a larger New England vacation, here are great day trips in Massachusetts with kids.

We’ve experienced a few of these things at no cost for review. This post contains affiliate links, and a purchase/click through one of these links may result in a commission paid to us at no additional cost to you. All opinions are my own.

Things to Do in Massachusetts With Kids

You can’t talk about places to visit in Massachusetts without leading off with the capital city of Boston. Boston is filled with family activities and is one of the best places to visit if you are hoping to see historical sites. You can even choose to stay in Boston and take various day trips from Boston as well as explore the city.

To get an overview of the sites of Boston, consider the popular Duck Boats (book in advance – they sell out!) as well as the trolley tours. This can be a good way to see everything quickly and get a good understanding of the history of Boston.

There are also several great museums to visit in Boston. For younger kids, the Boston Children’s Museum offers so many fabulous hands-on exhibits as well as a large climbing feature that’s perfect for burning off energy. Visit early in the day for lower crowd levels, because it definitely can get busy.

There are other fantastic museums in Boston. These include the New England Aquarium, the Boston Museum of Science , and the Boston Museum of Fine Art. All have elements that kids would enjoy.

Our favorite of these is the Museum of Science because there are so many different hands-on things for kids to do. Stay for an IMAX or planetarium show, and you’ll be there for most of the day. The museum also features traveling and interactive exhibits. It’s a great place to learn about science and have fun and there’s something for kids of all ages.

The New England Aquarium, located on the Boston Waterfront, offers both indoor and outdoor exhibits focused on marine life. It also features an IMAX theater offering nature-themed movies.

The Boston Museum of Fine Art is probably best for older kids. In addition to the art galleries, there is also a popular mummy exhibit that kids enjoy. They do have some kids’ programming throughout the year, so check their website for details.

If you are interested in history, be sure to walk the Freedom Trail. You can book a walking tour, or walk it on your own.

A walking tour is a great option for families looking to learn more about the history of the Freedom Trail. There’s also the Tea Party Museum and the USS Constitution along with other historic sites. Here’s one walking tour that can be booked in advance .

For theater and culture, you can see a show from the Boston Symphony Orchestra at Symphony Hall or a play/musical in the theater district. Several theaters rotate touring productions of national shows.

Local productions, including the Blue Man Group, are also available. There’s also the A.R.T. in Cambridge which offers shows (sometimes pre-Broadway) on a regular basis. There are also several live music venues.

In the summer, you’ll want to spend some time on the water. There are several different boat tours on the Boston Harbor that you can take, including whale watches and the thrilling Codzilla ride . Or take a trip to the Boston Harbor Islands , where you will get a national park experience right near the city.

Sports fans will definitely want to visit Fenway Park. If you can’t get tickets to see a game, take a tour of the park . This behind-the-scenes experience is perfect for fans of baseball.

You may also want to explore the more iconic areas of Boston, including Boston Common, the Boston Public Garden, and Faneuil Hall.

If you are planning to visit multiple attractions in Boston, it’s a great idea to purchase a Boston CityPASS. With the CityPASS, you’ll pay for one ticket and then get admission to multiple attractions. Here’s what’s included:

• The New England Aquarium
• The Boston Museum of Science
• Boston Harbor Cruises
• A choice of either the Franklin Park Zoo or the Harvard Museum of Natural History

Visit the CityPASS website to purchase .

See where to stay in Boston with kids here .

Salem, which is famous for the Salem witch trials from the 1600s, is located about 40 minutes outside of Boston on the North Shore and is one of the best day trips from Boston. This city offers waterfront views, shops, restaurants, and historic buildings among the Salem Witch attractions. If you’d like to learn more about the trials, the Salem Witch Museum has staged exhibits.

You’ll also find the acclaimed Peabody Essex Museum art museum right in the center of town, the House of the Seven Gables, the Nathaniel Hawthorne Birthplace, and more, just a short walk from the center.

As you’d imagine, Salem comes alive during the month of October for Halloween. While it’s a busy place to visit, there’s so much activity and so many great things to do.

Halloween lovers should definitely include a trip to Salem on their bucket list. Public transportation is offered, or arrive early for the best shot at a good parking spot. It gets extremely busy during the entire month of October. Here are some tours in Salem to book .

See hotels in Salem here .

I absolutely love Rockport, located on Cape Ann. Although I grew up in New England, I only started visiting Rockport a few years ago.

Since then, we’ve been a number of times, in summer and winter. It’s one of my favorite small towns. The entire Cape Ann area is a beautiful spot for a scenic drive, and it’s just a short drive from Boston.

If you visit the Rockport area, you’ll definitely want to go to Bearskin Neck. This neighborhood features shops and restaurants (lots and lots of seafood spots) in a quaint setting. You can park in one of the municipal lots or find on-street parking.

While you are there, you’ll definitely want to take a picture of Motif #1, which is rumored to be the most painted building. This iconic building is a replica of an old fishing shack.

Want to be on the water? You can rent kayaks in Rockport, or drive to neighboring Gloucester to take a whale watch or schooner tour. There are also several sandy beaches in the area worth visiting, including Wingaersheek Beach and Good Harbor Beach.

You can stay in Rockport or Gloucester, or make a day trip from another spot in Massachusetts.

See hotels in Rockport here .

Known as America’s Birthplace, Plymouth is a must-visit for anyone who wants to explore US colonial history. Plymouth is located about 75-90 minutes outside of Boston, towards Cape Cod. It’s a great place to stop either for a day trip as part of a road trip down to Cape Cod .

Once you are there, you’ll want to visit the Plimoth Patuxet Museum . This living history museum features several sections, including the Wampanoag Homesite and the 17th Century English village. It’s definitely worth a visit, especially with kids who are just learning about the colonization of America.

There are several different ticket options, which you can either purchase online or at Plimoth Patuxet. You can choose to visit just the plantation or add on visits to the Grist Mill and/or the waterfront exhibit. The Mayflower II was being restored in Mystic, CT, but is now back home in Plymouth.

Of course, if you are interested in history, you probably won’t want to miss Plymouth Rock. In reality, it’s a pretty small spot and isn’t very exciting. If you are already in the area, you may want to visit just to see it. But there are other better places to visit if you are short on time.

See hotels in Plymouth here .

I could dedicate entire articles to all of the kid-friendly things to do on Cape Cod . It’s truly a full vacation experience, especially in the summer.

Best visited in the summer (or early fall), Cape Cod is filled with quaint shops, clam shacks, and other restaurants, family activities, beaches, and great hotels. One popular attraction is the Cape Cod National Seashore , which is part of the National Park Service. The Cape Cod National Seashore includes beaches all the way to the tip of Cape Cod in Provincetown . The beaches in Cape Cod, are some of the best beaches on the East Coast.

When we visit Cape Cod for at least an overnight stay, we like visiting the Sea Crest Beach Hotel , which is located right on Old Silver Beach in Falmouth. It’s perfect for that quintessential family beach experience.

Another great resort option is Ocean Edge Resort , located in Brewster. Ocean Edge offers so many family activities, including special programming during school vacations and holidays. It has many different types of lodging, from rooms to villas.

In addition to beaches, you’ll also find museums such as the Whydah Whaling Museum and the Heritage Museum and Gardens in Sandwich. Mini golf is another popular summer activity, and make sure you get a famous lobster roll at some point on your vacation.

See hotels in Cape Cod here .

Take a ferry from the mainland (or fly in) for a getaway to Nantucket. This island is located about 30 miles from the mainland in Hyannis but feels almost like another country. It’s relatively small, about 47 miles total, but there’s lots to do.

Activities include nature walks, biking, beaches, and shopping. We love the Nantucket Whaling Museum, which offers a view of Nantucket’s history as a whaling city. It’s very busy in the summer, but late spring and early fall can also be a great time to visit.

Ferries do book up during the busy season, so make reservations in advance. Car ferries are available, but we prefer to stay right in town and walk around.

There are several different resort/hotel options on Nantucket, including the White Elephant right in town. See more hotel reviews here .

Martha’s Vineyard

Located about 4 miles from the coast of Cape Cod is Martha’s Vineyard. This island, larger than Nantucket, has several different towns to visit.

It has more activities than Nantucket and is a shorter ferry ride. While you are there, you can visit beaches, shop, eat delicious food, bike, take nature walks, and more.

There are several towns on the island, all with different things to offer. These include Edgartown and Oak Bluffs. Like Nantucket, you can bring your car on the island if you book a car ferry. Because Martha’s Vineyard is pretty big, I’d recommend bringing your car if you’d like to explore the island.

See hotels on Martha’s Vineyard here .

Springfield

Closer to Western Massachusetts is Springfield, Massachusetts. While Springfield isn’t a major tourist city in Massachusetts, it’s home to a few places you may want to check out, either for a day trip or on your drive out of Massachusetts.

In the fall, it hosts the Eastern States Exposition, which is one of the top ten fairs in the country. Taking place over 17 days in the late summer/early fall, the Big E (as it’s called) offers agriculture events, concerts, amusement rides, fun amusement-park food/snacks, and more. It’s fun to visit at least once with your family.

Springfield is also home to the Basketball Hall of Fame and the Dr. Seuss Museum. Basketball lovers should definitely visit the Hall of Fame at least once. It doesn’t take too long to tour, although there are events and activities that also take place there.

Six Flags Over New England is located in nearby Agawam and is open in season. Springfield is located about 2 hours from Boston and three hours and fifteen minutes from New York City.

See hotels in Springfield here .

The Berkshires

The mountainous region in Western Massachusetts is a popular summer vacation destination. You’ll find culture, farming, art, and outdoor activities. In the summer, visit the Boston Symphony Orchestra’s summer home, Tanglewood.

See hotels in the Berkshires here .

Fitchburg is home to the Boston-area Great Wolf Lodge resort. Guests of the resort can enjoy a number of fun kids’ activities including a huge indoor water park, an arcade, and a ropes course, among other activities. You’ll have to stay on the property to use the water park, so plan an overnight stay.

Guests can use the water park on both check-in day and check-out day. See our full Great Wolf Lodge New England Resort here.

Sturbridge MA, located west of Boston, features Old Sturbridge Village. It’s New England’s largest outdoor living history museum. You can learn all about life in the 19th century in New England from various historians throughout the exhibits. If you are headed to New York, Sturbridge is on the way.

Want to learn more about the American Revolution? Travel west of Boston to Concord Massachusetts, where you can visit Minute Man National Historical Park. There are various events offered throughout the year, but you can visit at any time to explore the park. Here are some tours of Concord you can book .

South of Boston, near the Rhode Island border, is Fall River. This waterfront city is home to Battleship Cove, an attraction that offers five historic naval ships, including the USS Massachusetts.

Outside of Massachusetts

Massachusetts is a relatively small state, and some of the best day trips can expand beyond Massachusetts. Options include Newport, Rhode Island, where you can explore the Newport Mansions and the beautiful Cliff Walk, as well as Salem New Hampshire, where you can visit the amusement park Canobie Lake Park.

Frequently Asked Questions

I would recommend staying in Boston. If you want to do a lot of things in one particular area, you may want to drive there and spend one or two nights.

Absolutely, you should have a car. If you are only visiting Boston, you may not need one. But if you are going beyond Boston, you’ll want a car.

Boston’s Logan International Airport is a major airport with many daily flights. It’s likely to be the most convenient airport.

The post 14+ Day Trips in Massachusetts With Kids appeared first on Family Travel Magazine .

Fans gather in Boston for the Red Sox home opener at Fenway Park

BOSTON (WGGB/WSHM) - Major League Baseball was back in Boston for the first time this season on Tuesday. The sun was out, there’s not a cloud in the sky, and there are plenty of fans at Fenway Park from far and wide to enjoy the Red Sox home opener.

“Opening day at Fenway Park, it doesn’t get any better than that for baseball,” said Ernie Candelmo of Hollywood, FL. “I like the atmosphere…the dedication that the fans have for their sports up here. That’s probably the biggest thing.”

Candelmo was one of many at Tuesday’s sellout home opener for the Sox at Fenway. He’s followed the team from spring training to the home opener and he said that first pitch always hits home. “It brings back a lot of memories throughout my childhood and playing baseball…always looking forward to the Red Sox home opener. I’ve been cheering for them as long as I can remember,” Candelmo added.

That’s what’s special about Boston baseball. They’re always there, through the good and bad.

“I’ve been with them since 1965…A lot of troubling times since then, a lot of disappointments…I’ve got to see a few World Series…rings and championships…it’s a lot of fun,” Candelmo explained, “My favorite memory was home opener in 2005 because that was when we all got to come and celebrate the end of the curse,” said West Springfield native Roberta (Ferrarini) Sepeinza.

Sepeinza pointed out they’re still doing much of the same. “It’s the celebrating of the tradition…where were we 20 years ago? and who are we now?” Sepeinza added.

They’re the Boston faithful.

“Go Sox,” Candelmo said

Copyright 2024. Western Mass News (WGGB/WSHM). All rights reserved.

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Eclipse watchers stuck in heavy traffic driving home: "Worst traffic I've ever seen"

By Megan Cerullo

Edited By Aimee Picchi

Updated on: April 9, 2024 / 2:37 PM EDT / CBS News

Drivers returning home Monday from watching the solar eclipse in cities and towns in the path of totality described traffic jams that were among the worst they'd ever experienced, keeping them on roads all night and into Tuesday morning. 

Indeed, cities and towns in the eclipse's path experienced some of their  largest influxes of tourists in their histories, providing  an economic boom  to states from Texas to Vermont. While eclipse tourists tended to stagger their arrivals during the weekend leading up to the event, many departed roughly at the same time after the eclipse ended on Monday afternoon, clogging highways and local roads.

Traffic on I-89 in Vermont, which links Burlington, a city in the path of the totality, with Boston, and on the state's I-91 was heavy on Monday afternoon, according to the Vermont Agency of Transportation. "Worst traffic I've ever seen," wrote Richard Chen of the venture fund 1confirmation on X, formerly known as Twitter, after visiting northern Vermont to view the eclipse. But, he added, "[I]t was totally worth it."

It took us over 6 hours to drive 110 miles in MO. last night after the eclipse. I’ve never been in that long of a traffic jam. The majority of it we were only going 8 miles an hour. I guess that’s the price you pay for center line totality! Cell service was out too!🤯 pic.twitter.com/GGVkXEcLn7 — Anne Jones (@1neatgirl) April 9, 2024

Along I-75 near Dixie Highway around Perrysburg, Ohio, motorists were stuck in miles of bumper-to-bumper traffic, according to a local media report . 

Michigan residents who had driven to Ohio to watch the eclipse described their return trips as taking twice as long as they should have, according to WTOL 11. 

The Maine Department of Transportation said the state had 10 times the volume of normal traffic in its western and southern regions Monday evening, according to Fox23 Maine . Most eclipse watchers departed at around the same time on Monday, even though they had arrived at different points leading up to the eclipse, according to The Maine Turnpike Authority.

The Maine DOT had earlier advised visitors to arrive early and leave late to avoid congestion on the roads. 

On TikTok, user @schoolhousecaulk said he had anticipated bad traffic in Vermont and that it was "worth it," despite driving overnight for 150 miles at a "snails pace."

At 5:30 in the morning, he said he finally reached his home in New York City. It had taken him 13 hours to drive 370 miles, he said. 

Megan Cerullo is a New York-based reporter for CBS MoneyWatch covering small business, workplace, health care, consumer spending and personal finance topics. She regularly appears on CBS News Streaming to discuss her reporting.

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Celtics Make Rare NBA History by Not Attempting a Single Free Throw vs. Bucks

• Author: Tom Dierberger

The Boston Celtics made a bit of unique NBA history Tuesday night in their 104–91 loss to the Milwaukee Bucks at Fiserv Forum.

The Celtics did not attempt a single free throw the entire game. All 10 Boston players who stepped on the floor—from star Jayson Tatum in 37 minutes to reserve Svi Mykhailiuk in seven minutes—did not earn a trip to the charity stripe.

Boston goes down as the first team in NBA history to not attempt a free throw in a full game.

"Another day in the NBA," Tatum said after the game when asked about the Celtics' strange feat. "Maybe just gearing up for the playoffs, they let a lot of things go. I guess [they] are just getting us ready for playoff basketball."

Jayson Tatum reacts to the Celtics becoming the first team in NBA history to not shoot a free throw in a game 🗣️ pic.twitter.com/oEsasTf4FU — Celtics on NBC Sports Boston (@NBCSCeltics) April 10, 2024

Additionally, the Bucks only shot two free throws—a pair attempted by superstar Giannis Antetokounmpo in the first quarter before he exited the game with a calf injury —adding another layer to the odd record-breaking night. The two combined free-throw attempts from Boston and Milwaukee go down as the lowest total in NBA single-game history.

There were 12 total fouls called in the game, eight on the Celtics and four on the Bucks. Celtics guard Jaylen Brown (three) and Bucks forward Khris Middleton (two) were the only two players who were whistled for multiple personal fouls.

Crew chief Marc Davis, referee Bent Taylor and umpire Danielle Scott will go down in history as a record-breaking officiating crew .

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