florida keys food tours islamorada

Florida Keys Food Tour

Review Highlights

“ Sheryl is from the area, therefore, very informative of the local history (& people) and restaurants..... ” in 5 reviews

“ I did this food tour on Black Friday and it ended up being a private tour with Craig . ” in 5 reviews

“ We tried coconut shrimp , key lime pie, fish tacos, fresh squeezed juice, a Cuban sandwich, watermelon salad and more. ” in 3 reviews

Location & Hours

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81650 Overseas Hwy

Islamorada, FL 33036

Serving Islamorada Area

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About the Business

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Food for the belly and for the soul! Join a local guide for a stroll thru Islamorada's cultural district. Sample some of the freshest and best food on the island, at locally owned restaurants. You may recognize a few stops that you have seen featured on The Food Network. Visit a brewery, a gallery or two, see one of the most historic neighborhoods in Florida, and hear tales of our island, past and present. Enjoy discounts later in your stay that are exclusive to our tour guests, so book early during your visit to our little island home. …

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Overall rating

I really enjoyed this walking food tour around Islamorada. Everything we tried was delicious that I will be sure to visit those same places again. The tour not only highlighted great eats, but was full of history, art, and Islamorada culture. Craig was a great tour guide. Thanks for the wonderful day food hopping around town!

See all photos from Alexandra C. for Florida Keys Food Tour

Jun 16, 2023

You are most welcome. And thank you for taking the time to share your thoughts and your photos from the tour. We are so glad to hear you enjoyed your time walking around Islamorada with me (Craig) and appreciate all the delighful tastes tastes, history, culture and more. Enjoy the rest of your time in the Florida Keys. -Craig

Craig and his assistant, Bob gave a great tour today! We stopped at several places to try lots of delish bites from fish tacos to shrimp fritters to key lime pie and even a few tastes of beer! They both were full of stories of the history of Islamorada and even some of the movies and shows filmed here. Highly recommend taking the tour! There is a walking one but we did the golf cart ride!

Dec 8, 2023

Thank you Sheri, I'm so glad you found our local tastes delicious and appreciated our stories too. Plenty of history here in Islamorada (Florida Keys) to share too... and we love sharing it wirh our guests. Thanks so much foro hopping on our golf cart tour and recommending us. We appreciate it. -Craig

If you are thinking about going on this tour......do it! I went with a group of 7 other women for a 50th birthday celebration and it was so much fun! We started out at 10:30 in the morning and met at Library Park in Islamorada. Our guide, Sheryl, had everything planned out perfectly! We walked to about 10 different stops; some we're just points of interest in the Keys, and some were actual food & drink stops. We started at The Trading Post Grocery Store, which Sheryl explained was the oldest grocery store in the Keys. It is still family owned, and there we each got a' mini key lime pie. Next we went behind the building to a cute little park with cozy seating areas in a beautiful tropical setting. This area is also the home of Bad Boy Burrito where we each had a soft taco and a delicious hibiscus tea. My taco was made with Kobe beef & it was yummy! My friends who had the fish taco, made with Covina said they were a highlight of the trip. Most of us ate our little pies here as well and they were fantastic! Next we stopped at the Bloodline filming site for Kevin's Marina. (There was a Bloodline theme to the tour and many of the restaurants and bars we visited had been used in various scenes of the series.). Next we went to the Shrimp Shack where the seafood lovers got to try coconut shrimp and a conch fritter and the non-seafood lovers got a delicious little salad with fresh strawberries, mandarin oranges, and blue cheese. Everyone was happy with their food, and the owner came by to give us a brief history of her experiences owning restaurants in the Keys. We walked some more and learned about many places like the Florida Keys Hurricane Memorial and we even saw the childhood home of our guide. Plus we got to sample 2 unique craft beers at the Florida Keys Brewing Company & try 2 chowders, conch & turtle, at the historic Green Turtle Inn. Our final stop was the Islamorada Fish Company where we were each given a side of fish dip with crackers & veggies. This is a big restaurant that had live music and lots of outdoor seating with great views of the water. We were also able to relax and order from the bar on our own if we chose to. We ended up very close to where we had parked and all of the locations were within a mile and a half of each other. It was a fun way to enjoy each other's company while sampling some new cuisine and learning some history about the Florida Keys. Of course our host, Sheryl, made the tour even better because she was so knowledgeable and had everything set up so smoothly. I highly recommend this tour!

See all photos from Lisa T. for Florida Keys Food Tour

This tour is great for both locals and visitors! Yummy food and fascinating stories about the keys. Will take again for sure!

Oct 2, 2023

Always a joy to have locals on our tour… and it’s lovely to hear you appreciated the food and the keys stories…. We appreciate the 5 star review. Plus thanks for also letting us know you’d take the tour again - that’s one of the best compliments we can receive. -Craig

We got inside scoop on the area, as well as local food, history and Bloodline deets on this tour. Highly recommend it. Craig was an insightful guide who seemed to tailor info based on our interests. We enjoyed eating fish tacos and hibiscus tea at Badboy Burritos (5/5), a conch fritter and a coconut shrimp at Shrimp Shack (4/5), fish dip from Islamorada Fish Co. (3/5) a beer flight at Florida Keys Brewing, a Cuban (3/5) and Key Lime Pie (5/5) from the Trading Post. Since the tour, we've enjoyed binging the first season of Bloodline seeing sights that were on the tour.

Feb 29, 2024

We sure do offer the inside scoop on our tours and do tailor each one to our audience.... Also, very glad the food was enjoyable too, we curate our locally favorite tastes for our guests to enjoy. We certainly look to tailor the experience to our guests each tour and appreciate you leaving us a 5 star review. stay loving the keys, Craig

Highly recommend this food, history, culture, art, and a little Rayburn (Netflix's show Bloodline) sprinkled in tour. Very well informed tour guide. Among the favorite things we did on our trip to Hollywood and the Keys. Islamorada is fantastic and this tour hit all the great spots. Food was generous and absolutely delicious. A total highlight of our entire 8 days on vacation. Great customer service at each spot. We enjoyed the food so much that we returned a few days later on our way back from Key West to Hollywood to eat at two of the places again! Just a wonderful experience. We are seasoned food tour guests and this one was among the best we've done anywhere. If you do nothing else is Islamorada, do this food tour!

Apr 19, 2023

So glad you enjoyed your time on the tour. We take pride in making sure you learn about our history, culture, art along with tasting our island cuisine. Plus it always makes me happy to hear people return to the restaurants we showcase on the tour too. And then to be one of the best from a seasoned food tour connoisseur well that's just music to our ears. Thanks again.

Absolutely loved this tour! I had a hard time figuring out where to park but once I arrived we were up and rolling! I did this food tour on Black Friday and it ended up being a private tour with Craig. It was an absolutely amazing food tour, one of the best I have been on. I got to try a great amount of food and food I have never had before. The turtle chowder was absolutely amazing and it was my first time having it! I learned a lot of history and got to see a lot of Bloodline filming locations. What an awesome tour! Thank you so much Craig and everyone!

See all photos from Katrina W. for Florida Keys Food Tour

Fantastic food tour! I gave my brother a ticket to the Florida Keys Food Tour as a birthday gift. We ended up having five in our party alone as several family members wanted to join the fun. Everyone loved it - ages 12 to 65! Sheryl, who owns and operates the tour was amazing. She grew up in Islamorada so her stories were awesome! First hand accounts of so many things, so historical and interesting. No one could do this tour better. We went to like five different restaurants and a brewery, the Hurricane Monument, a gallery and Red Cross house...and more. In my opinion, everyone who loves the Keys should do this food tour! What's better than great food, fascinating history and time spent among friends? We tried coconut shrimp, key lime pie, fish tacos, fresh squeezed juice, a Cuban sandwich, watermelon salad and more. Along the easy walk, we made friends and learned so much about the area - from a local who grew up right in the midst of it all. I can't recommend this tour enough. A must-do.

See all photos from Jill M. for Florida Keys Food Tour

This is not only a fun tour, but the food at each spot is delish and unique. Do not be afraid to try the unusual dishes! And although I lived in the keys 8 years of my childhood, I still learned alot of history about the keys and those who settled there first. If you're a Bloodline fan, you'll see the actual sites where they film. Would definitely recommend (preferably in the cooler months), and bring along friends to share in the fun!

See all photos from Ibby G. for Florida Keys Food Tour

If you are ever in the Keys you must try this food tour. Not only do you get to taste great food but you also get the history of Islamorada. The tour guide was raised in Islamorada and knows first hand a lot of the events that went on in that part of the Inland. My husband and I went on this tour last year and enjoyed it very much.

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Florida Keys Food Tours - All You Need to Know BEFORE You Go (2024)

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Florida Keys Food Tour

• 152 Sioux St Tavernier, FL 33070
• (305) 394-1028

Visit our Instagram for more photos

Our signature Florida Keys Food and History tour takes you on a leisurely stroll through beautiful and historical downtown Islamorada, the heart and jewel of the Upper Keys. You will see why our food tour is one of the premier things to do in the upper and middle Keys. Stop by on your way to Key West for our lunch time tour.

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Islamorada Chamber of Commerce

Official Islamorada Visitor Information from a local point-of-view

Call an Islamorada Vacation Specialist! 800-FAB-KEYS 305-664-4503

Islamorada is home to some of the best dining in the Keys. From quick bites to elegant candle-lit dinners, there are options for every occasion. Many restaurants will even cook your catch! During our annual “Taste of Islamorada,” restaurants compete for recognition in a variety of categories, and there are a lot of local award winning dishes waiting to be savored! Enjoy!

When you purchase through links on our site, we may earn an affiliate commission. Details here .

Best Things to Do on Islamorada in The Florida Keys

Julie Diebolt Price

The writer was hosted.

The breathtaking sunsets in Islamorada paint the sky in shades of purple and never fail to amaze tourists and residents. This spectacle can be traced back to the early Spanish explorers, who were mesmerized by the vivid hues of the setting sun and the surrounding waters.

The purple hue is caused by a combination of atmospheric conditions, such as the scattering of light by particles in the air and the reflection of light off the water. This unique phenomenon has made Islamorada, which means “purple island” in Spanish. a popular destination for photographers and nature enthusiasts. I am one of them.

What You Need To Know About Islamorada

Islamorada is known for….

Key Largo is known for diving, Key West is known for sunsets, and Islamorada , halfway between the two, is known for fishing. While the resorts have private sandy beaches, people come to Islamorada for fishing and snorkeling rather than the beaches, according to a local.

Islamorada is about 90 minutes south of Miami on the Overseas Highway. It’s known as the “Sportfishing Capital of the World” because Islamorada hosts the largest fishing fleet per square mile in the world.

The Netflix family-drama series Bloodline was filmed in Islamorada , and the series takes place on the beach at the Moorings Village and Spa .

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• Casa Morada Review: A Tranquil Paradise in the Florida Keys

When Is The Best Time To Visit The Florida Keys

The best months to visit the Florida Keys are December through April. The weather is mild and pleasant, with temperatures ranging from the mid-70s to low 80s Fahrenheit. This time of year also offers the best fishing and water sports conditions.

November and May are transition months between seasons. Hurricanes occur in the summer, and temps are hot and sultry.

The busiest months on the Florida Keys are December through February.

Where Is Islamorada

Between Key Largo and Key West lie the Plantation, Upper Matecumbe, and Lower Matecumbe Keys. Islamorada is known as the “Village of Islands” due to its unique geography. Islamorada is between Mile Markers 80 and 90 in Monroe County.

The islands are surrounded by the Atlantic Ocean and the Gulf of Mexico (called the bay side), making it a popular destination for water activities such as fishing, boating, and snorkeling. The islands are connected by the Overseas Highway, which offers stunning turquoise water views.

Read More: Hawk’s Cay Resort Review: Family Fun in the Florida Keys

How Big Is Islamorada

In terms of demographics, Islamorada has a population of around 7,000 residents. The island is approximately 20 miles long and offers a variety of landscapes, including stunning beaches, mangrove forests, and crystal-clear waters.

Things To Do In Islamorada

Regarding things to do in Islamorada , there is something for everyone. A visit to the History of Diving Museum is a must for history enthusiasts. It showcases the evolution of diving equipment and the history of underwater exploration.

For dining options, Islamorada is known for its fresh seafood. Numerous oceanfront restaurants offer delicious seafood dishes like stone crab claws, lobster, and locally caught fish. Some popular dining spots include Lazy Days Restaurant , Islamorada Fish Company , and Ma rker 88 .

Fishing is a major attraction in Islamorada, often called the “Sportfishing Capital of the World.” The island offers excellent opportunities for both offshore and backcountry fishing. You can charter a boat and try your fishing skills for marlin, sailfish, tarpon, and many other species.

Water sports are also a big part of the Islamorada experience. You can go snorkeling or scuba diving to explore the vibrant coral reefs and marine life. Kayaking and paddleboarding are popular for those who prefer a more relaxed water adventure. That would be me!

Islamorada is a paradise for nature lovers, history buffs, and outdoor enthusiasts. Its unique geography, diverse demographics, and various activities make it a fantastic destination to explore.

Casa Morada As Home Base

Casa Morada is a centrally located boutique hotel in Islamorada and was my home base for exploring these Florida Keys islands. It is known for its luxurious and intimate atmosphere, making it a great place to stay for those looking for peace and relaxation. The hotel offers stunning ocean views and a serene environment.

Casa Morada , rated #1 on TripAdvisor, boasts a private beach where visitors can relax, swim, and participate in various water sports. The hotel’s rooms are elegantly decorated and equipped with up-to-date facilities, guaranteeing a pleasant stay. In addition, Casa Morada offers a swimming pool, a spa, and a restaurant that provides tasty meals.

Florida Keys Food Tours

My first choice to learn about Islamorada history and dining options is the  Florida Keys Food Tours , a walking tour through Paradise in historic downtown Islamorada, where TV shows Bloodline and Diner, Drive-ins and Dives were filmed.

When I learned about their tours and what they covered, I realized this is the best overview one can have with a limited amount of time on the island. When I spoke with the owner, Craig Zabransky, I realized their programs offer the perfect overview of things to do, including historical sights, local art, and sampling the best of the local Keys island-style cuisine.

Sharing 200 years of Keys history, the Florida Keys Food Tours offers a meeting with chefs, learning about island foods, introducing the art scene, historic landmarks, and more. I’m looking forward to learning how to blow the conch shell.

Islamorada Itinerary

If you are planning your trip to Islamorada in the Florida Keys, as I am right now, you may wonder where to start.

When I begin planning my itineraries, I locate on a map where I will be staying. On this trip, I will be at  Casa Morada , centrally located in Islamorada. This location is great because I won’t have to double back on attractions. As I drive south on Highway 1, the Overseas Highway, I will stop at attractions on the way down before I check into the hotel, making the most of my first day.

On the second day, I’ll take the food tour, which is a comprehensive introduction to Islamorada, and will visit the attractions on the island’s south side.

 On the third day, I will catch attractions I haven’t seen yet or take a boat tour of the outlying islands on a charter boat.

Planning the itinerary this way, I’m sure to see the highlights without going back and forth, or in this case, up and down the islands.

Islamorada Attractions

Working from the north just past Tavernier at Mile Marker 91.5, here is a list of Islamorada attractions traveling south on the Overseas Highway.

Rain Barrel Village

The Rain Barrel Village , easily found because of the giant Florida Keys spiny lobster at the entrance named Betsy, is a tropical garden and open-air complex. Specialty shops, boutiques, and galleries offer local art, custom jewelry, handmade crafts, and unique souvenirs.

This is the perfect stop for a selfie because Betsy is one of the most photographed landmarks in the Florida Keys.

Windley Key Fossil Reef Geological State Park

Key Largo limestone, a fossilized coral reef, makes up the Windley Key Fossil Reef . The limestone was used to build Henry Flagler’s Overseas Railroad in the 1900s. The quarry was used until the 1960s to produce Keystone, a decorative stone.

Five self-guided nature trails show off the natural beauty of Islamorada. The visitor center features exhibits, quarry machine samples, and ancient coral reef cross-sections.

Theater of the Sea

Theater of the Sea , family-owned since 1946, is in a tropical garden setting. Home to various marine life like sea turtles, fish, sharks, sea lions, stingrays, alligators, dolphins, and birds, their mission is to provide a wonderful home for their animals and share it with visitors.

Regularly scheduled shows run throughout the day from 9:30 am to 4:30 pm. Guests can interact with dolphins and sea lions or swim with sharks.

History of Diving Museum

Over forty years, Drs. Joe and Sally Bauer collected many diving helmets, air pumps, suits, lights, gear, memorabilia, prints, photographs, books, films, and videos. They incorporated it into a museum in 2000, and the History of Diving Museum  showcases their contributions from over 30 countries to the history of diving. It’s become the largest and most comprehensive collection in the world.

Henry Flagler’s Overseas Railroad

Henry Flagler co-founded Standard Oil with partners John D. Rockefeller and Samuel Andrews. For more than a century, Standard Oil was the world’s largest and most profitable corporation.

Henry Flagler built the Overseas Railroad from the fossilized coral limestone from the quarry owned by the Florida East Coast Railroad, Flagler’s resources and imagination. Flagler connected the entire east coast of Florida from Jacksonville to Key West and intended to take advantage of the Panama Canal to open up trade.

Flagler also built hotels and resorts along the Atlantic Coast of Florida and ushered in the Gilded Age in the late 1800s.

Florida Keys History and Discovery Center

The Discovery Center , located on the property of the Islander Resort, permanently exhibits a replica of Indian Key circa 1840, along with stories about the Overseas Highway, the people who created lives for themselves in the islands, and much more.

Hurricane Monument

The  Hurricane Monument  is a memorial to the 408 people killed in the 1935 Labor Day hurricane at Mile Marker 81.5. Carved out of the local coral limestone, the monument honors those who died in the strongest hurricane to hit the US.

Pioneer Cemetery

Located at Mile Marker 82, the Pioneer Cemetery is a small collection of statues, sand, and graves surrounded by a white picket fence. The Pinders, Parkers, and Russells were pioneers in the 1850s and settled in Islamorada.

Florida Keys Brewing Co.

The first Upper Keys microbrewery,  Florida Keys Brewing Co ., is in the Morada Way Arts and Cultural District. With a rotating selection of seasonal and barrel-aged beers, you can enjoy a draft beer while you check out the artwork, play some games, or listen to music. The FKBC distillery infuses its beer with local flavors like Key limes, local honey, and citrus.

Morada Way Arts & Cultural District

The primary thoroughfare between the iconic Green Turtle Inn and the Hurricane Monument is a six-block corridor called the Morada Way Arts and Cultural District . This bustling corridor boasts studio spaces, restaurants, and art galleries integrated with parks, bike baths, and businesses.

Gallery openings, local artists, live music, food, and libations are featured on the third Thursday of every month.

Green Turtle Inn

The Green Turtle Inn , a famous Islamorada landmark since 1947, became known for its sea turtle specialties harvested from the local waters. Today, the “Turtle” has an Old Florida laid-back vibe and offers fresh seafood, steaks, and classic American dishes.

Indian Key Historic State Park

Indian Key was the first county seat for Dade County in 1836. It was home to a profitable business that retrieved valuable items from shipwrecks in the Florida Keys. Today,  Indian Key  is an uninhabited ghost town. You can hike, swim, sunbathe, visit the observation tower, and take the self-guided interpretative tour at this historic site.

Only accessible by kayak now due to storm damage on the boat ramp, Indian Key Historic State Park is an offshore island. It is open from 8 am until sundown every day of the year. Local charter companies offer kayak rentals.

Lignumvitae Key Botanical State Park

A wealthy Miami chemist by the name of William J. Matheson, bought the tiny island of Lignumvitae  in 1919, the year my dad was born. Matheson built a caretaker’s home with a windmill for electricity and a cistern to store rainwater. Today, this structure is the visitor center for the island forest, a virgin tropical hardwood hammock.

The Lignumvitae Key is accessible only by boat or kayak. Florida Keys Boat Rentals provides a ferry service at Robbie’s Marina on Fridays, Saturdays, and Sundays. Check their website for details and schedule.

Robbie’s Marina

  Robbie’s of Islamorada  is a must-visit when you are in the Florida Keys. It is the place to connect it all, from snorkeling trips, offshore fishing, eco-tours, and jet ski adventures in mangrove tunnels to kayak and paddle board rentals.

I plan to feed the giant tarpon fish, see great art, and pick up a few souvenirs when I’m there. You can book a day trip at Robbie’s to visit the historic islands only accessible by water or sunset cruises later in the day.

Islamorada Sandbar

Less than a mile offshore, near Mile Marker 84, is the famous Islamorada Sandbar on the Atlantic Ocean side. During the summer and holiday weekends, the sandbar is overwhelmed with boats, lounge chairs, BBQ grills, and picnic tables submerged underwater.

The sandbar is only accessible by water. Therefore, a charter company like KeyZ Charters  will help you get there. If that scene is too much for you, KeyZ Charters can also take you to other shallow beach areas on a personal sandbar boat tour that includes Key Largo, Marathon, and all of the Florida Keys.

Alligator Reef Lighthouse

There are no alligators at Alligator Reef Lighthouse  because they are freshwater reptiles. You are more likely to see crocodiles, and then, rarely. The lighthouse was named after the USS Alligator, a US Navy schooner that ran aground on the reef and sank in 1822.

The 150-year-old lighthouse is about four nautical miles east of Indian Key over the island chain’s barrier coral reef. The only way to get there is by boat.

Sea Oats Beach

The sand berms between the beach and Overseas Hwy at Sea Oats Beach sustained significant damage from Hurricane Irma in 2017. Red streetlights were installed to protect the sea turtle hatchlings on this nesting beach to keep them from entering the road. White streetlights attract the hatchlings because they mistake them for the moon.

Anne’s Beach

Located at the southern end of Lower Matecumbe Key at Mile Marker 73.5, Anne’s Beach  is a local favorite and was featured in the Netflix series, Bloodline . The shallow water, boardwalk, and covered pavilions with picnic tables and benches are the last stop on my Islamorada itinerary.

Environmentalist Anne Eaton is memorialized at this little beach. Eaton fought to preserve and protect the area and wildlife of Islamorada . Hidden behind mangrove trees, this shallow beach with clear waters is a great place to learn to snorkel because there are no waves—the perfect place for me.

One response

It is always so much fun to read a post about your home town, so glad you enjoyed your time visiting. and I am impressed about how much you did when visiting Islamorada…. Plus, super glad to see you enjoyed your time on the Florida Keys Food Tour too.

I look forward to reading more about your adventures.

Stay loving the cuisine, culture and cocktails of the keys, Craig

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FLORIDA KEYS FOOD TOURS (Islamorada) - All You Need to Know BEFORE You Go

The Perfect 5 Day Florida Keys Itinerary for First Timers

In this article, I’m sharing the perfect 5 day Florida Keys itinerary, ideal for first time visitors. The Florida Keys are a pretty epic American road trip destination. You’ll find yourself driving along an overseas highway, hopping between different tropical islands.

I’m basing this itinerary off my most recent trip to the Florida Keys, in which I road tripped from Miami Airport to Key West and back again with my friend Mary, exploring multiple keys along the way.

Highlights of this 5 day Florida Keys itinerary include:

• Snorkeling in the USA’s first underseas park
• Key lime pie… lots of key lime pie
• Beach resorts and bed & breakfasts
• Fishing (and then eating your fish for dinner!)
• Sunset sailing
• Exploring a tropical fruit grove
• Driving the Seven Mile Bridge
• Touring a sea turtle hospital
• Visiting Key West classics like the Ernest Hemingway House

Let’s get to it.

5 Day Florida Keys Itinerary: An Introduction

This 5 day itinerary is designed for first time visitors to the Florida Keys to give you an overview to each of the main keys. Maybe you have been to Key West before, but this is your first time exploring the keys as a whole.

Did you know that the Florida Keys are made up of about 1,700 islands, all connected by a 113-mile overseas highway? Yep, you’ll be road tripping over water in this epic itinerary.

This 5 Day Florida Keys Road Trip Itinerary:

Miami > Key Largo > Islamorada > Key West > Marathon > Miami

How Many Days Do You Need in the Florida Keys?

In my experience, five days is the minimum amount of time required to road trip the Florida Keys, if you’re planning to visit more than just Key West.

Below I’m sharing the ideal Florida Keys itinerary for first timers, spread across five full days. Note that I say five full days, because this itinerary does involve travel in and out of Miami Airport on days 0 and 6.

Here is a quick day-by-day breakdown of my recommended way to spend 5 days in the Florida Keys:

• Day 0 : Fly into Miami
• Day 1: Miami > Islamorada
• Day 2: Islamorada
• Day 3: Islamorada > Key West

Day 4: Key West

• Day 5: Key West > Marathon
• Final Day: Marathon > Miami

You can read my itinerary in much more detail below. I’ve designed the itinerary with general activity lists, rather than restricting you hour-by-hour, because I think that’s more helpful (and digestible, as a reader!).

Let’s get to it!

Car Rental for a Florida Keys Road Trip

You’ll need to rent a car for this Florida Keys road trip, unless you live in Florida or are driving down!

Reserve your rental car at least a few weeks in advance, to avoid any car shortages. Then, pick it up at the rental car counter at Miami Airport.

I recommend Discover Cars for car rental in the Florida Keys, because they show you the best deal from many different companies. You can filter by your personal preferences, such as size of car or insurance level.

Day 0: Fly to Miami

Highlights: Arrival to Miami, pick up rental car.

Your task for “day zero” is just to fly into Miami (or Fort Lauderdale) and pick up your rental car. Of course, you could do this early on your first full day instead, but personally I enjoyed doing this the night before so we had a fresh start for our road trip in the morning!

Where to Stay

Stay somewhere close to the Miami Airport. We stayed at the AC Hotel Miami Airport West for one night and I recommend it. It was a quick drive from the Miami Airport, and the hotel itself was sooo nice and comfortable with some high tech amenities.

Where to Eat

Have a quick dinner. For your first night, I recommend you just grab a quick meal before the adventure starts tomorrow.

Mary and I actually popped by Chipotle for takeout, which we ate in our room at the AC Hotel!

Doral City Place is another option very close to the AC Hotel Miami Airport West. It’s a large shopping center with lots of restaurants.

Fly into Miami. Obviously!

Pick up your rental car. This took us a surprisingly long time (1 hour) with the lines at the car rental station, so be sure to account for that possibility.

Relax in hotel. Mary and I actually ended up watching The African Queen (which we were able to play via Youtube on the massive TV in our AC hotel room ). This was as “research” for our steamboat ride on day 1 – read about that below!

Day 1: Miami to Key Largo to Islamorada

Highlights: A steamboat tour, fisheries lunch, check into beach resort.

Drive time: 2 hours

The first full day of your 5 day Florida Keys itinerary is all about the upper keys. You’ll spend the day driving from Miami down to your beach resort in Islamorada, which takes about 2 hours in total with some fun stops along the way in Key Largo (the northernmost key).

Day 1 | Miami to Key Largo to Islamorada:

• Check out of AC Hotel Miami Airport West
• Drive to Key Largo (~1.5 hours)
• 10am pre-booked steamboat tour on The African Queen
• Lunch at Key Largo Fisheries and Backyard Cafe
• Key lime pie at Keys Chocolate and Ice Cream
• Drive to Islamorada (~30 minutes)
• Check in to Postcard Inn Beach Resort
• Dinner at Twisted Shrimp
• Cocktails and beach sunset at Postcard Inn

I recommend booking a beach resort in Islamorada. We stayed at Postcard Inn Beach Resort for two nights. This was a great central location for the two days of our itinerary that we spent exploring the upper keys.

Postcard Inn is special because it’s directly on the ocean, and guests have access to paddle boards, kayaks, bikes, and more.

Fun fact: this resort is also where the rum runner cocktail was invented! Obviously, we had to partake.

Book your stay at Postcard Inn here.

RELATED | Best Places to Stay in the Florida Keys (For All Budgets)

Lunch at Key Largo Fisheries (Key Largo). This is a very “keys” experience and perfect for lunchtime. Eat some super fresh fish or crab (or lobster!) and see the nurse sharks swimming off the dock.

Key lime pie at Keys Chocolate and Ice Cream (Key Largo). If you are like Mary and I, then you’ll obviously waste no time in getting your hands on some key lime pie.

I recommend stopping at Keys Chocolate and Ice Cream after lunch for their chocolate-covered key lime pie on a stick (and yes, it was gluten free!! Read my guide to finding gluten free key lime pie in the Florida Keys here ).

Dinner at Twisted Shrimp (Islamorada). A roadside seafood restaurant where you can actually eat IN a boat!

This place is extremely on brand for the keys.It’s laidback, family owned, and the (gluten free) fried shrimp is a delight. It is a great stop for dinner on your first night!

RELATED | Gluten Free Key West and the Florida Keys Guide

Cocktails at Postcard Inn’s Tiki Bar. You HAVE to visit the Tiki Bar for obvious reasons – this is reportedly where the rum runner cocktail was invented!

Go on The African Queen Steamboat Tour. Taking this historic steamboat tour is the highlight activity of the first day of your 5 day Florida Keys itinerary. This is literally THE boat that featured in the 1951 adventure film starring Humphrey Bogart and Katharine Hepburn. It’s actually on the U.S. National Register of Historic Places.

I recommend booking a tour for 10am, which is what we did. This was good timing as it gave us ample time to drive down from Miami, and we finished in time for lunch.

It was somewhat surreal sitting in this boat, cruising through the Key Largo canals and out to the ocean and back, after just having watched the movie the night before. Check availability and book your tour here .

Day 2: Islamorada and Key Largo

Highlights: A snorkel tour, charter fishing, and catch-and-cook dinner.

The theme for day two is adventure in the upper keys! This is your day to go snorkeling at the famous John Pennekamp Coral Reef State Park – the first undersea park in the United States!

Unfortunately for Mary and I, it was very windy on this day of our Florida Keys road trip… so our snorkel tour got CANCELED! This was a huge bummer, but nature happens, my friends.

The Keys can be particularly windy so it’s not unheard of for water activities to get canceled. With that in mind, we still had a wonderful day and were able to go charter fishing in the afternoon.

Day 2 | Islamorada and Key Largo:

• Quick breakfast
• 9am snorkeling tour at John Pennekamp Coral Reef State Park (alternatively: swimming and paddle boarding at Postcard Inn’s beach)
• Lunch at The Fish House
• 1pm fishing charter trip
• Relax at Postcard Inn and get ready for dinner
• “Catch and cook” dinner at Chef Michael’s

You’ll spend a second night at your resort in Islamorada. We spent our second night at the wonderful Postcard Inn . I enjoyed having two nights in Islamorada, despite this being a pretty fast-paced 5 day Florida Keys itinerary.

Postcard Inn was a good home base to drive around the upper keys from. Plus, it was so great to have direct beach access, especially after our snorkel tour got canceled!

Quick breakfast. I recommend having a quick breakfast on day 2, because your itinerary today is pretty packed! Mary and I grabbed some food from the Starbucks by Postcard Inn (notably: the last Starbucks for 90 miles!).

Lunch at The Fish House Restaurant and Seafood Market (Key Largo). I stopped here for lunch to try their famous “Matecumbe” sauce which is essentially fresh fish simmered up with capers, shallots, and other delights. This dish has been featured multiple times on the Food Network – for good reason. Highly recommend!

Dinner at Chef Michael’s (Islamorada). For dinner, Mary and I dressed up and dined in style at Chef Michael’s (reservations recommended). Actually, we ate the fish that we caught earlier that day on our fishing trip – so fun!

This is also the place to try Lionfish – by eating it you are supporting their efforts to cull this invasive species and save the nearby reefs.

Snorkeling tour at John Pennekamp Coral Reef State Park. Ideally, you should spend the first half of your day enjoying an epic snorkeling tour off the coast of Islamorada.

Tours last 2.5 hours and depart 9am, 10:30am, 12pm, 1:30pm, and 3pm (for this itinerary, I recommend booking the 9am). Book your tour ahead of time here .

Fishing trip with Bamboo Charters . After lunch, head out on the water again but this time with Captain Matt Bellinger of Bamboo Charters. He’s an experienced fisherman, and will help you catch some Florida Keys fish no matter your experience level.

On our trip, we caught a lot of small snapper, which we saved for a catch-and-cook dinner at Chef Michael’s (arrange this with Captain Bellinger ahead of time). We also had an extremely thrilling hour-long struggle with a giant sting ray – don’t worry, we released it!

Fishing charters can be booked for 8am or 1pm, in groups up to six people, and you can choose a 4-, 6-, or 8-hour option. For this itinerary, I recommend the 4-hour 1pm-5pm option. Book your fishing charter here .

Relax at the beach. Your other job for today? Chill out and enjoy the beautiful Florida Keys beach – with direct access from Postcard Inn !

Of course Mary and I were disappointed when our snorkel tour was canceled, but this didn’t stop us from taking the paddleboards out at Postcard Inn.

Day 3: Islamorada to Big Pine Key to Key West

Highlights: A tropical fruit farm, the Seven Mile Bridge, and Cuban food in Key West.

Today you’ll get back into road trip mode, by driving down to Key West and passing over the famous Seven Mile Bridge. The total drive time from Islamorada to Key West is two hours, but you’ll take some fun stops along the way – including a picnic lunch at a very unique tropical fruit farm!

Day 3 | Islamorada to Big Pine Key to Key West:

• Check out of Postcard Inn
• Breakfast at Mangrove Mike’s
• Visit Florida Keys History & Discovery Center
• Drive to Big Pine Key (~1 hour)
• Visit Grimal Grove Tropical Fruit Farm
• Drive to Key West (~1 hour)
• Check in to The Gardens Hotel
• Cuban food for dinner and Sloppy Joe’s

I recommend staying at The Gardens Hotel in Key West. This was our home for two nights, and I loved it. This hotel is historic, quaint, and has a lovely breakfast and pool.

The location is ideal – you can walk anywhere you want to go in Key West but it’s a couple blocks back so never gets too loud at night. There’s also champagne on arrival and on site parking.

Book your stay at The Gardens Hotel here.

Breakfast at Mangrove Mike’s (Islamorada). Start your day off with the most Americana vibes diner you could imagine, just a five minute drive from Postcard Inn.

I particularly loved that they had gluten free pancakes! Definitely recommend eating breakfast here on at least one of your days in Islamorada.

Picnic lunch. For lunch, I recommend having a picnic, either at Bahia Honda State Park or at Grimal Gove (a tropical fruit grove that I share more about below!).

Dinner at El Meson de Pepe (Key West). You just have to try Cuban food in Key West and this is a great family-owned place to do it, recommended by locals and easy walking distance from your hotel if you stay at The Gardens Hotel.

Visit the Florida Keys History & Discovery Center (Islamorada). After breakfast, your first stop of the day should be this history museum. It’s in Islamorada and only a five-minute drive from Postcard Inn, so it’s an easy way to start our day. During our visit, I learned a LOT about the Florida Keys (did you know it was originally an overseas railroad?).

Drive the Seven Mile Bridge. Your drive today includes this incredible landmark. After passing Marathon and before reaching Big Pine Key, you must first drive over seven miles of turquoise ocean.

Take a tour of Grimal Grove . I absolutely recommend making time to stop at Grimal Grove, a tropical fruit grove in Big Pine Key with a super unique back story. This is the only breadfruit grove in the country and tours include “tropical fruit hunting” and a fun tasting session where you eat breadfruit curry, fried breadfruit, sugarcane juice, and more (AKA, lunch!).

Tours last 75-90 minutes and are available Tuesday to Saturday at 10:30am, 1pm, or 3:30pm (I recommend the 1pm time slot for this itinerary!). Book your tour here .

Get settled at your hotel. After driving another hour, you’ll arrive in Key West! Check in to your hotel (I recommend booking The Gardens Hotel ) where you’ll be staying the next two nights.

Check in involves a complimentary glass of champagne, and you may even have time to jump in the pool and say hello to the resident cat and tortoise!

Drinks and nightlife on Duval Street. After a delicious Cuban dinner, make the most of your first night in Key West with a trip to the iconic Sloppy Joe’s – the bar that Ernest Hemingway frequented in Key West. Just a warning: it’s going to be crowded… and sloppy!

The entirety of Duval Street will be bustling, so if Sloppy Joe’s isn’t your vibe then you still have plenty of bars to pick from.

Highlights: full day to explore Key West, literary walking tour, key lime pie, museums, and sunset sailboat tour.

Today you can put the car keys away and devote a full day to exploring Key West!

There are honestly so many things to do in Key West but I’m sharing my personal ideal one day schedule below. If I was to extend this 5 day Florida Keys itinerary into a full week or longer, I’d give extra days to Key West because you only really get a taster with one full day.

Still, it’s a pretty epic day. If you follow my itinerary below, you’ll spend today eating key lime pie, drinking Cuban coffee, exploring on a literary tour, visiting historic sites, and sailing into the sunset with a drink in hand!

Day 4 | Key West:

• Breakfast at The Gardens Hotel
• Coffee from Cuban Coffee Queen Roasters
• 10am Literary Walking Tour by Key West Literary Seminars
• Lunch at Date & Thyme
• Eat some key lime pie
• Museum visit
• Sunset sailing tour with drinks and live music
• Dinner at Half Shell Raw Bar

We stayed a second night at The Gardens Hotel , and I recommend you do, too. I took advantage of the hotel’s amenities by swimming in the pool early in the morning!

Key West is the highlight of the Florida Keys for many people, so you definitely want one full day and two nights here.

Breakfast at The Gardens Hotel . Since our hotel was a bed and breakfast, we just went downstairs to eat a lovely breakfast out on the garden patio!

Coffee at Cuban Coffee Queen. This was a great stop to try the classic Cuban cafe con leche.

Lunch at Date & Thyme. You can really eat lunch anywhere today, but my personal recommendation would be this lovely organic market and cafe. They specialize in grab & go meals like wraps (and ice cream sandwiches!) and have plenty of vegan and gluten free options.

ALL the key lime pie. You’re in Key West, after all, so dedicate some time today to trying key lime pie! We did this directly after lunch.

Top 3 places to get key lime pie in Key West:

• Kermit’s Key West Key Lime Pie Shoppe
• Key West Key Lime Pie Company
• Key Lime Pie Bakery

RELATED | Where to Find Gluten Free Key Lime Pie in Key West

Dinner at Half Shell Raw Bar. For dinner tonight, embrace being by the seaside and head to this casual and quirky bar located in the Key West Historic Seaport.

It will be convenient after your sunset sailing trip ends (more on that, below!). I recommend at least one platter of oysters.

Go on a literary walking tour. Key West is known for its vibrant literary history. If, like me, that interests you, then be sure to go on this 1.5 hour tour. You’ll walk through the Old Town of Key West, visiting the homes and haunts of writers like Ernest Hemingway, Robert Frost, Tennessee Williams, Shel Silverstein, and Elizabeth Bishop.

Tours are offered Sundays and Wednesdays at 10am. If that doesn’t match your schedule, you can contact them about a private tour. The cost is $30 per person, and you can book your tour here .

Visit Judy Blume’s bookstore, Books and Books. This is another one for my fellow book worms. Whether or not you go on the literary walking tour you should definitely check out the Books and Books bookstore – this is owned by none other than Key West local author, Judy Blume! You may even see her during your visit.

Explore Key West’s historic sights. After your literary morning, lunch, and a sampling of key lime pie, it’s time to spend your afternoon on more traditional touristic pursuits.

Key West has SO many museums and historic sights. You can really only scratch the surface in one day (but don’t worry, you’ll also have time to visit some sights tomorrow morning).

Here are some museums and sights to see in Key West:

• Harry S. Truman Little White House
• Key West Lighthouse and Keeper’s Quarters
• Ernest Hemingway Home and Museum
• Mel Fisher Maritime Museum
• Key West Aquarium
• Tennessee Williams Museum

Personally, Mary and I chose to visit the Mel Fisher Maritime Museum this afternoon. That may seem like an odd choice but we really wanted to see some of the less well-known side of Key West and this museum was fascinating!

Take a sunset sailing trip . Finally, end your day in Key West with an incredible sunset sailboat trip out into the ocean, complete with complimentary cocktails and live music.

Mary and I took this exact sailing trip with Sebago Watersports and it was such a lovely way to end the day. There’s nothing like a Key West sunset seen from the ocean!

Book your sailing tour here.

Day 5: Key West to Marathon

Highlights: Southernmost Point, Ernest Hemingway Museum, Key West Lighthouse, Turtle Hospital, and a stunning beach resort.

Drive time: 1 hour

This is the final full day of your 5 day Florida Keys itinerary, but it’s still packed full of fun activities!

You’ll spend the morning exploring more of Key West, including the Southernmost Point and any museums you missed the day before. Then, you’ll drive north to Marathon where you’ll tour the famous Turtle Hospital, and check in to your hotel where you’ll have an incredible al fresco dinner by the beach.

Day 5 | Key West to Marathon:

• Breakfast at The Gardens Hotel (alternatively Green Pineapple cafe)
• Check out and hold luggage
• See more Key West sights
• Lobster pizza lunch at the Seaside Cafe at the Mansion
• Drive to Marathon
• Check in to Isla Bella Beach Resort
• Turtle Hospital Tour
• Relax at Isla Bella
• Dinner at Mahina at Isla Bella

You have a couple options of where to stay tonight, depending on when your flight home is. I recommend staying the night in Marathon, before driving back to Miami Airport the following morning. This maximizes your time and gives you 5 full days in the Florida Keys.

Alternatively, if you are flying home on day 5, then you may have to skip some of the itinerary below to drive back to Miami Airport in time for your flight.

Personally, on our final night in the Florida Keys we stayed at Isla Bella Beach Resort in Marathon. This was an incredible accommodation to end our trip on.

It’s luxurious yet surprisingly affordable, directly on the water with pools, beaches, bikes, and beautiful docks with sunrise views. There are also a few restaurants on site and this is where we had dinner – one of the best meals of our trip by far.

Book your stay at Islabella here.

Breakfast at your hotel or in town (Key West). Get an early breakfast today so you can get out and explore Key West. Either eat the complimentary breakfast at The Gardens Hotel , or check out Green Pineapple Cafe , a favorite of mine which opens at 8:30am.

Lunch at Seaside Cafe at the Mansion . Before you depart Key West, grab a quick lunch at this truly iconic restaurant that’s just steps from the Southernmost Point. Come here for their famous lobster pizza – it will not disappoint!

Dinner at Mahina at Isla Bella . Dress up and enjoy a final dinner in the Florida Keys at this Polynesian inspired restaurant at Islabella, where you can dine al fresco under the stars with a backdrop of ocean waves.

The filet mignon is to die for, and top it off with a key lime pie martini! Reservations required.

Spend the morning exploring Key West. There is so much to see in Key West so you’re bound to have some places you still want to go after your full day in Key West yesterday. This is your time to visit them – just check out and have your hotel hold your luggage first!

On our final morning in Key West, Mary and I climbed up the Key West Lighthouse , before taking a tour of the Ernest Hemingway Home (a MUST when in Key West!) and hugging The Kapok Tree .

Then, we checked out the Southernmost Point marker, before getting a lobster pizza lunch. It was a pretty packed morning!

You could easily do the same, or change it up and visit any of the other sights I listed previously.

Turtle Hospital tour (Marathon). This was one of the highlights of my whole Florida Keys road trip! Marathon is home to a world class sea turtle rehabilitation center, and it’s actually open to the public to visit.

Tours are offered on the half hour, from 9am to 4pm, and cost $35 per person. Reservations are highly recommended! Book your tour here .

Relax at Isla Bella . After your turtle hospital tour, return to your hotel and relax before dinner. Soak up your final hours in the Florida Keys!

If you stay at Isla Bella Beach Resort like we did, then I recommend taking a dip in one of the pools.

Final Day: Marathon to Miami Airport

Highlights: Pigeon Key, drive to Miami Airport and fly home.

Drive time: 2.5 hours

All good things must come to an end. On your final day in the Florida Keys, your main job is to check out of your hotel and drive back to the Miami Airport (~2.5 hours driving time) to return your rental car and fly home.

Be sure to give yourself ample time to drive back to Miami before your flight, especially if you’re driving on a Friday or Sunday, due to traffic!

If you have time before you check out, consider taking the complimentary bikes at Isla Bella and riding to Pigeon Key and back. I also recommend checking out the Marketplace at Isla Bella before you leave – it’s an epic 5,000 square foot space with a cafe, perfect for picking up some souvenirs (and lunch for the road) before you depart!

If You Have More or Less Time on Your Florida Keys Roadtrip…

You can shorten or extend my suggested itinerary as needed, based on your flight times.

If I had to cut a night from my 5 day Florida Keys itinerary above, it would perhaps be the final night in Marathon (and just drive directly to Miami Airport). However, Isla Bella Beach Resort was my favorite hotel and a wonderfully relaxing way to end the trip, so it really depends on your travel style.

On the other hand, if I could add days to this itinerary and make it a full week in the Florida Keys, then I’d add a full day in Key West. Another day in Islamorada also would have been useful due to the weather cancellation of our snorkeling trip.

For the ultimate relaxation, I’d also add a couple days at Deer Run on the Atlantic , a sustainable bed and breakfast on Big Pine Key. A girl can dream!

5 Day Florida Keys Itinerary: Final Thoughts

That completes my 5 day Florida Keys road trip itinerary… I hope it’s helpful to you as you plan your own trip to the Florida Keys.

If you have any questions, just leave me a comment below. Happy traveling, and enjoy the Florida Keys!

Check out my other Florida Keys blog posts…

Best Places to Stay in the Florida Keys

Gluten Free Key West and the Florida Keys: Complete Guide

Where to Find Gluten Free Key Lime Pie in Key West

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Best Places to Stay in the Florida Keys For All Budgets

Gluten Free Key West and the Florida Keys: The Complete Travel Guide (2024)

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Reader's Digest

Your Guide to a Florida Keys Road Trip: Key Largo to Key West

Posted: March 12, 2024 | Last updated: March 13, 2024

Your road trip guide to the Florida Keys

One of the best state road trips in America has to be the sun-kissed drive from Key Largo to Key West in the Florida Keys. This road, known as the Florida Keys Overseas Highway, takes you through a 125-mile island chain that begins just south of Miami. It hopscotches over 42 bridges and five islands, and has turquoise waters stretching in every direction into the Atlantic Ocean, Florida Bay and Gulf of Mexico.

So if you're looking for the perfect Atlantic Coast road trip or cheap beach vacation , look no further than this road trip guide from Key Largo to Key West. And if you'd rather travel from Key West to Key Largo, rest easy—the route works either way. There are shuttles that run from Key Largo to Key West, but keep in mind, you'd be missing out on all the fun in between.

By the way, once you embark on the Florida Keys Overseas Highway, you'll notice that many sites along the way use mile markers (MM) in their address. We use those mile marker points in this story to help you navigate the drive.

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Mile marker: 108–90

The first of the Florida Keys you'll hit after driving about an hour south from Miami en route from Key Largo to Key West is, well, Key Largo. Often referred to as the Dive Capital of the World, Key Largo includes one must-see stop: John Pennekamp Coral Reef State Park (MM 102.5), the first underwater preserve in the United States.

Experienced and novice snorkelers and SCUBA divers will be enthralled by the teeming marine life that lives just below the water's surface, like parrot fish, barracudas and sea turtles. More experienced divers enjoy exploring the USS Spiegel Grove, one of the largest ships ever intentionally sunk to create an artificial reef where pretty fish can thrive.

Back on dry land, travelers can wander nearly six miles of trails at Dagny Johnson Key Largo Hammock Botanical State Park, home to more than 80 species of plants and animals. You can also peruse the work of local artists at myriad galleries.

Best beach: Cannon Beach, found within John Pennekamp Coral Reef State Park, has shallow waters that are perfect for wading. You may even spot cannons and anchors on the beach that remain from a 1715 Spanish shipwreck.

Where to eat: Dig into the catch of the day at The Fish House, Key Largo Conch House or Snook's Bayside Restaurant & Grand Tiki Bar, some of the best traditional restaurants in the area. If you'd rather turf than surf, check out Jimmy Johnson's Big Chill.

Where to stay: If you can't get enough of the underwater world, stay at Jules' Undersea Lodge , the world's first underwater hotel. If you'd rather keep dry, try the adults-only Bungalows Key Largo .

Mile marker: 90–63

Next up en route from Key Largo to Key West is the fisherman's paradise known as Islamorada. Considered the Sport Fishing Capital of the World, it's where backcountry sport fishing and saltwater fly-fishing got their start. Countless seasoned boat captains are ready for hire to take you out to catch the wahoo, marlin, mahi-mahi and tuna that swim in these waters.

There's an even quirkier way to interact with fish here: hand-feeding the tarpon off the docks of Robbie's Marina (MM 77.5). Since 1976, countless Keys visitors have stopped to feed them, and more than 100 kinds of fish gather at the docks for their daily snacks. Feeding the fishies there is so popular, it's been named the No. 1 activity in all the Florida Keys.

Islamorada is also a terrific spot to kitesurf, stand-up paddleboard, go for a hike or take a bicycle ride. Stop by the Laura Quinn Wild Bird Sanctuary, where injured or displaced birdies now make their homes. Or visit the History of Diving Museum, which boasts one of the world's largest collections of diving helmets.

Best beach: Anne's Beach is popular with families (and dogs) because of its shallow waters and lack of waves. Take a walk along the boardwalk or enjoy a picnic at one of the covered tables.

Where to eat: For a quintessential casual Florida Keys meal, go to the Hungry Tarpon. If you want more elegant fare, make reservations at Chef Michael's for creatively inspired local dishes.

Where to stay: When it's time to lay your head for the night, check in to one of the new oceanfront suites at Cheeca Lodge & Spa , or your own cottage at The Moorings Village & Spa .

Mile marker: 63–40

Marathon is the island chain's top boating destination—and for good reason. The area boasts nearly 2,400 boat slips and plenty of facilities to accommodate sailors passing through. But you don't need your own boat to enjoy Marathon and its waters.

For a truly different experience, hop on over to Cruisin' Tikis and have a floating tiki bar adventure. Sunset, mangrove and harbor cruises are all available, as is a swim-stop cruise for a chance to jump into the water.

While you're here, you should also visit Pigeon Key, an island that is accessible by boat, trolley or walking the 2.2-mile Old Seven Mile Bridge. It has a museum to explore, either on a guided tour or on your own. The Bridge is open for walking, running, bicycling, rollerblading and, of course, watching the killer sunrises and sunsets.

Best beach: Sombrero Beach is one of the prettiest beaches in the Florida Keys—not to mention one of the best beaches in Florida . And it's not just popular with humans; sea turtles nest here between April and October.

Where to eat: For any meal, stop by Castaway, which has been serving guests for more than 70 years. Or make a night of it at Hide Away Café, which has an extensive wine list.

Where to stay: The Faro Blanco Resort & Yacht Club is set on the waterfront and gives you a taste of marina life. Lime Tree Bay Resort on Long Key has spacious townhomes for rent.

The Lower Keys

Mile marker: 40–4

After crossing the Old Seven Mile Bridge out of Marathon, you'll find yourself in the Lower Keys, where natural habitats and wildlife refuges thrive. It's no wonder this part of the Florida Keys is known as the Natural Keys. You might even want to consider taking an electric vehicle on this road trip so you don't disturb the animals.

Your best chance to spot a native Key deer, a subspecies of the Virginia white-tailed deer that somehow made its way south, may be in the National Key Deer Refuge, comprised of 9,200 acres stretching from Bahia Honda Key to Sugarloaf Key on the edge of the Gulf of Mexico. More than 20 endangered and threatened plant and animal species can be found within the refuge. Take a quiet walk at dusk or dawn for your best chance to glimpse a Key deer, or join a ranger-led tour to learn more about the area.

Aside from all the eco-friendly fun, Stock Island is well worth a stop. Their maritime history goes back generations, and the marina is filled with shrimping and fishing boats. Artists have been flocking to Stock Island, too, and share their works in galleries dotted across the small island.

Best beach: The shallow, clear water and white sand at Calusa Beach make it a locals' favorite. The beach is a perfect spot for snorkeling too.

Where to eat: In addition to the freshest of seafood, Big Pine Rooster serves up ribs and a special-recipe meatloaf. Or sip like the locals at No Name Pub, located on Big Pine Key.

Where to stay: Consider the waterfront Sugarloaf Lodge , stay in an Airstream at Big Pine Key Resort  or pop a tent on one of the reserved campsites at Bahia Honda State Park.

Mile marker: 4–0

You've made it to the end! Closer to Cuba than Miami, Key West is known for its nightly sunset celebrations, party atmosphere and laissez-faire vibe, but it's really so much more.

If you're a writer or bookworm, you'll certainly want to make plans to visit the Ernest Hemingway Home & Museum, where you should keep an eye out for the famous six-toed cats. Then wander through Key West's Bahama Village, a 12-block area of historic homes and restaurants.

Consider a day trip to Dry Tortugas National Park, about 70 miles west of Key West in the Gulf of Mexico, where you'll find some hidden gems . The island, accessible by boat or seaplane, is popular for snorkeling and feeling like you're on your own private island, not to mention touring the Civil War–era fort.

Best beach: Fort Zachary Taylor Beach—or Fort Zach, as locals call it—predates the Civil War and boasts the island's very best sandy stretch.

Where to eat: No visit to Key West is complete without a meal at Blue Heaven, where you can dine with wandering roosters for breakfast, lunch and dinner. Or snag a spot on the tiny balcony at Santiago's Bodega for tapas and flowing wine.

Where to stay: The boutique Gardens Hotel , the adults-only Kimpton Hotels Ridley House  or the new Capitana Key West , to name a few. Wherever you stay, you're sure to find your place in Key West, and it's likely you'll follow so many others' lead and start planning your return visit before you even leave.

Art and history in the Florida Keys

Road-tripping from Key Largo to Key West, it's easy to appreciate all the natural beauty. That said, the Keys aren't just a terrific destination for eco-travelers, but artists and history buffs too.

It's easy for artists to find inspiration throughout the Florida Keys. Fortunately for road-trippers, there are many spots to stop and admire their work. One of the largest artists' communities in the Florida Keys is Stock Island in the Lower Keys, just about three miles from the commercial area of Key West. What was once a shrimping boat marina is now a blend of fishermen and painters, sculptors and other artisans who have created an energetic and supportive community.

For history buffs, in addition to Pigeon Key in Marathon and the Civil War–era Fort Jefferson in Dry Tortugas National Park, other must-stops in Key West include the Audubon House & Tropical Gardens, Harry S. Truman Little White House and the Southernmost Point in the continental United States.

Planning your Florida Keys road trip

Now that you're inspired to hit the road, it's time to start planning. After budgeting for a road trip , your next step is to decide whether you will travel south from Key Largo to Key West, or north from Key West to Key Largo. Or maybe you'll opt for a roundtrip.

If you're starting off in Key Largo, it's important to note that the Florida Keys Overseas Highway begins at the Miami-Dade/Monroe County line. So if you're flying to Florida, Miami International Airport (MIA) is the way to go. If you begin in Key West, the airport (EYW) is on the island.

If you're already driving one of the best road trip cars to get to Florida, you're all set. But if you need a loaner, choose one of the best cars to rent for a road trip . Consider packing these road trip essentials and download some of the best podcasts for road trips to make the miles fly by.

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The Food Tour Opens Up for Summer

After nearly a two month break and travels, the Florida Keys Food Tour will open up again on August 8th to provide you the opportunity to taste the very best in Florida Keys cuisine.

The Islamorada Food tours will open with a special schedule until November when we kick back into our high season with a full schedule.  Take a look at all our tours and clcik Book a Food Tour Today from the homepage.

Food Tours Are Open

join us on a food tour on the fabulous Florida Keys

year, we expanded our options adding new tours, and come this August 8th – all 5 tours will have availability starting with our most popular oIslamorada Food Tour n Tuesday, August 8th.

• Islamorada Food Tour
• Local Happy Hour Food Tour
• Islamorada Sunset Happy Hour Food Tour
• Islamorada Golf Cart Food Tour
• Islamorada Golf Cart Happy Hour Food Tour

With a typically lighter schedule in these hotter, slower tourism months feel free to contact the tour directly if you do not see a tour on the days you are in town. The Florida Keys Food Tour always offers private tours, but we also have additional flexibility in these slower months too. So connect with us and I can potentially rearrange schedules if possible to accommodate your interests.

Summer Break

Leaving the Keys always provides a fresh perspective on living, working and of course eating on the rock. My travels provided a break from the grind, but also allowed me to appreciate the culinary delights of other parts of our country. Make sure you check the Instagram over the last month @flkeysfoodtours to see some of the delicious and regional foods I enjoyed on my travels.

But now I am back, and so are we, so the tours are available, so I hope to see you this “season.”

Stay Culinary Curious,  Craig

• FlKeys Food Tour News
• Florida Keys Food Tour
• Most Popular!
• Users Up to 12 People
• Hour Glass 4 Hours
• Info All ages

The Original Islamorada Food Tour

Our original Islamorada tour combines gastronomy, culture, history (throws in a bit of the Rayburns) and ties it all together by stopping in at Islamorada restaurants for tastes of their island cuisine.

• Users Up to 8 People
• Hour Glass 2 Hours

Islamorada Local’s Happy Hour Tour

A Fun Happy Hour Stroll! Experience a few of the local favorites on an afternoon happy hour stroll through a less touristy section of the Islamorada.

Islamorada Sunset Happy Hour Tour

Learn local history, appreciate unique tastes and sample delicious cocktails though an abridged walking tour in downtown Islamorada. Plus, enjoy a beautiful Florida Keys sunset!