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A Conch Home in Key West, Florida

Commonly referred to as America’s Caribbean, the Florida Keys are a string of tropical islands that stretch over 120 miles off mainland USA, between the Atlantic Ocean and Gulf of Mexico. If you’re a lover of the beach, warm weather, boating, snorkeling and Southern culture, then you must visit the Florida Keys and follow this road trip itinerary!

From north to south, the Florida Keys consist of Key Largo, Islamorada, Marathon, The Lower Keys and Key West. Whether you are someone who enjoys relaxing at a resort pool or beach; exploring our underwater world through Scuba diving or snorkeling; loves a good party; likes to fish or prefers to be on the water, there is something for everyone in the Florida Keys.

A woman touring the Hemingway House during a Florida Keys road trip itinerary

During February 2022, I did a wonderful Miami to Key West road trip with Caitlin of My Darling Passport. After spending a night in the Miami area visiting family, I picked up Caitlin at the airport and we drove to Key West together. It takes around three and a half to over four hours to drive from Miami to Key West. Our Florida Keys road trip itinerary first started with us exploring in and around Key West and we ended our trip relaxing in Marathon.

In this travel blog, discover the best Florida Keys itinerary for 4 days and read all about where we stayed in both Key West and Marathon during our girl’s trip.

**Please note that this blog post uses affiliate links meaning that if you make a purchase via my affiliate link, I receive a small commission at no additional cost to you. I only promote and talk about products and services that I have used and like. During my time in the Florida Keys, Oceans Edge Resort & Marina hosted me for one night and Isla Bella Beach Resort hosted me for two nights. I also partnered with the Florida Keys tourism board.


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Florida Keys Road Trip Itinerary

Planning a Trip to the Florida Keys:

Isla Bella Beach Resort in the Florida Keys

If you are planning a trip to the Florida Keys and only want to stay in Key West, I recommend flying to and from Key West International Airport. If you plan to do a Miami to Key West road trip and stop at various spots along the Keys, then I suggest flying into Miami International Airport. You can find affordable flights through Skyscanner.

For those looking to directly follow my Florida Keys road trip itinerary, you will need to rent a car to get around. If you plan to only stay in Key West, you can get around by utilizing public transportation like Uber, Lyft and city taxis. If you are staying at a hotel or resort in Key West, some of them offer a free shuttle service that will take you into the Old Town area and there is also the Duval Loop, which is a bus route that runs from the island’s Atlantic Ocean area to the Gulf section. The Duval Loop runs adjacent to Key West’s famous Duval Street that is lined with bars, restaurants, boutique shops and more. There are 18 stops along the route.

A cinema in Key West, Florida

In addition to the Duval Loop, you can also take Key West’s other forms of public transportation through The Key West Transit that connects throughout the island itself, along with Stock Island. The Lower Keys Shuttle is a great way to get from Old Town Key West to Mile Marker 53.5 in Marathon.

What I did was fly from Newark Airport in New Jersey to Miami International Airport and rented a car from there. I also flew home from Miami as well!

Driving to the Florida Keys from Miami is easy. There is only one highway, which is called Route 1, and during the prime season, the roads can be busy. Caitlin and I visited the Keys during the popular season and hit some traffic on our road trip.

(Click here if you are planning to road trip around the United States and want to rent an RV.)

Best Florida Keys Road Trip Itinerary:

Colorful houses in Key West, Florida

Day 1:

Drive from Miami to Key Largo:

I recommend beginning your Florida Keys road trip itinerary by heading out of Miami earlier in the day. If you’re looking to see as much as possible, then the earlier you leave, the better it is. There is only one highway in the Florida Keys, which is called Route 1, and there are a lot of beautiful spots you aren’t going to want to miss out on.

The first destination you reach when you officially get to the islands is Key Largo. If you are someone who enjoys exploring our underwater world, then you’re going to want to check out John Pennekamp Coral Reef State Park.

John Pennekamp Coral Reef State Park in Key Largo

Known as the first undersea park in the United States, John Pennekamp Coral Reef State Park includes mangrove swamps with coral reefs and an incredible marine life. Please note that when you visit John Pennekamp Coral Reef State Park, you will need to book an organized tour with a guide to participate in the water activities there.

The fun adventures you can choose from at John Pennekamp Coral Reef State Park are snorkeling and Scuba diving tours and a glass bottom boat tour. You can also rent kayaks, paddle boards and power boats. There are also camping, fishing, swimming and picnic areas throughout the park.

Visit Florida Keys Brewing Co. in Islamorada:

Enjoying craft beer from Florida Keys Brewing Co. during a Florida Keys road trip itinerary

As you continue to make your way down the Keys, you will next hit Islamorada. During your Florida Keys road trip itinerary, I recommend grabbing lunch and local craft beer at Florida Keys Brewing Co., located on Route 1.

Overall, Florida Keys Brewing Co. is the Upper Keys’ first microbrewery and it also includes a beer garden, tasting room and a food truck onsite. The entire brewery is colorful and in the beer garden, you can enjoy yard games like giant Jenga, cornhole and hula hoops. You can also listen to live music during your time at this spot.

On Monday through Saturday, you can savor authentic Mexican food from Jalisco Taco Truck and on Sundays, you can enjoy continental cuisine from A Movable Feast.

Relax and Stay at Oceans Edge Resort in Key West:

A woman enjoying the pool area at Oceans Edge Resort on Stock Island in Key West during a Florida Keys road trip itinerary

During our time in Key West, Caitlin and I stayed at Oceans Edge Resort & Marina, which is situated on Stock Island. This luxury resort is laid back and the perfect spot to vacation on Key West.

Oceans Edge Resort is situated on the marina and includes stunning guest rooms and suites, six saltwater pools to enjoy; a restaurant, café, pool bar and in-room dining and fun activities. Overall, it is a quiet haven just outside of Key West’s thriving Old Town.

A woman on vacation in the Florida Keys

When we first arrived in Key West, Caitlin and I checked into Oceans Edge Resort and relaxed by the pool during the afternoon. After a long winter, a nice day out in the sun was well needed!

Staying at Oceans Edge Resort & Marina:
A woman staying at Oceans Edge Resort & Marina during a Florida Keys road trip itinerary

Caitlin and I stayed in the Oceanfront 2 Bedroom Suite at Oceans Edge Resort. It was nice because we were staying in a pod that included two bedrooms, which means that we each got our own separate room and bathroom.

The Ocean View 2 Bedroom Suite includes one balcony king suite that has a king bed, an en-suite bathroom, a balcony that overlooks the marina and a separate seating area. The other room included two queen beds with an en-suite bathroom and a balcony that also overlooks the marina and pool area.

Key lime pie from Key West

When we first arrived, we were greeted with champagne and key lime pie. Savoring this delicious treat on our balconies was perfect! (Key lime pie is a staple to the Keys.)

I love the coastal style of Oceans Edge Resort & Marina. The furniture and décor will boost your mood from the moment you check in. I also love how each room has a balcony, so that you wake up with the ocean breeze in your face.

Click here to discover all the rooms and suites you can choose from at Oceans Edge Resort in Key West.

Amenities at Oceans Edge Resort:
Staying at Oceans Edge Resort & Marina in Key West

As a guest at Oceans Edge Resort there is a convenient and complimentary shuttle that takes you to and from the resort to Key West’s Old Town. It is around a 15-minute drive to get from the resort to the Old Town. The shuttle stops in front of the Waterfront Brewery and departs hourly between 9am to 11pm. It is great not having to worry about driving into downtown and finding parking and Uber/Lyft services can be quite expensive.

Oceans Edge Resort also has a full-service, 165-slip marina that hosts private watercraft, fishing charters and pleasure cruises. There is also a dry-dock facility.

During your Florida Keys road trip itinerary, I recommend checking out the eateries at Oceans Edge Resort. Yellowfin Bar & Kitchen is a seafood restaurant, bar and grill with stunning waterfront views. You can enjoy fresh fish, steak and chicken dishes as well as salads.

Oceans Edge Resort during a Florida Keys road trip itinerary

Oceans Edge Café is a great spot to have breakfast at the resort. You can wake up to fresh Cuban coffee, smoothies, breakfast sandwiches and baked treats. In addition, the poolside menu can be enjoyed throughout the day and it includes refreshing cocktails, peel-and-eat shrimp, jerk chicken, club sandwiches and burgers.

There is also so much fun to be had at Oceans Edge Resort. While you relax poolside, there are also games to enjoy such as giant chess, Connect Four and ping pong. You can also rent kayaks and paddle boards as well as bikes to take around Key West.

The resort also has a Marine Science Eco Experience, which is a one-hour program that educates guests on sea turtles, dolphin echolocation, lionfish, coral reefs and sharks. Complimentary yoga classes are also offered poolside on Tuesdays, Thursdays, Saturdays and Sundays at 8:30am. There are also paddle board fitness classes held on Mondays and Fridays at 8:30am.

Oceans Edge Resort & Marina also has movie nights and live music at Yellowfin Bar & Kitchen from Thursdays through Sundays from 6pm to 9pm. The hotel also is pet friendly and hosts weddings.

Have a Fun Evening in Key West:

Having fun on Duval Street during a Florida Keys road trip itinerary

A Key West road trip itinerary is not complete without having a fun night out on the island’s most historic neighborhoods – Old Town. Filled with fun bars, renowned restaurants and beautiful Conch-styled houses, Old Town Key West is fascinating and filled with a lot of culture. (Key West is also haunted! Click here to book a ghost tour.)

A popular spot in Key West to have fun at is on Duval Street. Similar to New Orleans’ Bourbon Street, Duval Street is the “main drag” in Key West and it is filled with over 200 bars and restaurants. Along Duval Street are also great souvenir and boutique shops.

Key West has lenient open container laws making it perfect for a bachelor and bachelorette party!

Savor a Nice Dinner at Café Sole:
A hogfish dinner at Cafe Sole in Key West, Florida
Lobster bisque from Cafe Sole
Key lime pie from Cafe Sole in Key West

During our first evening in Key West, Caitlin and I got dinner at Café Sole. This modern French-Caribbean restaurant is snuggled in a peaceful and charming neighborhood of Old Town Key West. I loved how dreamy and cozy it is! There is an outdoor terrace that has stringed lights and cozy seating.

Hogfish is the staple fish to the Florida Keys. If you can try hogfish during your time in Key West, I highly recommend it because it is delicious! During our dinner, I savored the hogfish with veggies and rice as my main meal. I also had lobster bisque as an appetizer. Everything was delicious! Caitlin had a salad with the linguine and clams’ dish and loved it as well. We both split the key lime pie as a dessert!

Listen to Live Music at Blue Heaven:
Having fun at Blue Heaven in Key West during a Florida Keys girl's trip

A fun place to enjoy great drinks and live music after dinner is Blue Heaven, located two blocks from Duval Street, on the corner of Petronia and Thomas Streets.

I loved how Blue Heaven has a fun, “Southern backyard” type of vibe, as I like to refer it as. There is a similar spot to Blue Heaven in New Orleans called Bacchanal Wine and I love how there is a lot of outdoor seating, stringed lights everywhere and just a happy ambiance. Also, the margaritas at this spot did not disappoint!

Day 2:

Explore the best Florida Keys Island:

A house decorated for Valentine's Day in Key West

My favorite area of my Florida Keys road trip was definitely Key West! I love the charming houses and neighborhoods, the fun and happy ambiance, the plethora of different restaurants to choose from and the overall culture it boasts.

Wake Up to Breakfast at Banana Café on Duval Street:
Inside Banana Cafe in Key West

One of the best ways to start the day is by grabbing breakfast at Banana Café. This adorable café has a nice rooftop with stringed lights, a patio looking out at Duval Street and a cozy indoor space.

Breakfast at Banana Cafe on Duval Street in Key West

I loved the breakfast we had at Banana Café! We split the Florida Lobster Eggs Benedict that came with butter-poached Florida lobster meat, avocado, two poached eggs with an English muffin and tomato along with key lime hollandaise sauce and breakfast potatoes. The second dish we split for breakfast was the Belgian Banana Foster Waffle with almonds.

Learn the History of Key West:
A Conch Victorian house in Key West, Florida

After breakfast, we walked everything off by exploring the different neighborhoods within the Old Town. There is a lot of history to Key West! It was originally inhabited by the Calusa and Tequesta Indians. The Spanish came to Key West in 1513 and Ponce de Leon was the one to discover the island.

Key West became a U.S. port of entry in 1823. It was destroyed by a fire in 1886 and in the early 1900s, Henry Flagler built his overseas railway to Key West, which was completed in 1912. U.S. Route 1 runs alongside the railway. Key West also became a large military base too.

Key West, Florida

In the early 1800’s, New England natives, Cubans and Bahamians lived in Key West. The colorful homes that you see around the island represent the history from each of those cultures.

The Conch Victorian houses are the most common homes in Key West. Bahamians built them like they were boats, using timber framing. Other popular forms of architecture you’ll find as you explore Key West are Shotgun Houses and Eyebrow Houses.

A Shotgun Home in Key West

Shotgun Houses are common throughout the American South. It is a narrow home that usually has a porch and a lot of character. According to folklore, Shotgun Houses got its name because a bullet shot can go through the front door and exit the back door without hitting anything. Eyebrow Houses include side-oriented gable-roofed buildings.

Another cool fact about Key West is that it is located at the southernmost point of the continental U.S. You can visit the Southernmost Point Buoy, which is one of the most iconic landmarks in the Florida Keys.

The Southernmost point Buoy in Key West, Florida

Overall, Key West is only 90 miles to Cuba, making it geographically closer to the country versus mainland Florida and Miami.

One of the best ways to get a great history lesson and tour of Key West is by taking the world-famous Conch Tour Train that takes visitors around the island’s most popular and iconic attractions.

Tour the Ernest Hemingway Home:
Visiting the Ernest Hemingway Home and Museum during a Florida Keys road trip itinerary

Ernest Hemingway was a famous American novelist and writer who was born in 1899 and died in 1961. Hemingway became inspired to visit Key West through artists and writers he met in Paris during the 1920s. He ended up getting to Key West from Havana, Cuba.

Inside the Ernest Hemingway Home in the Florida Keys

One of the best things to do in Key West during a Florida Keys road trip itinerary is to tour the Hemingway Home. It is a Spanish Colonial home that was built in 1851 and Hemingway and his wife purchased the house and renovated it in the early 1930s. It is now a National Historical Landmark.

Touring the Ernest Hemingway house in Key West

During a tour of the Ernest Hemingway Home, you will learn about the famous novelist and his life. As you walk throughout the house, you can see Hemingway’s personal touches such as unique European décor and furniture, antiques, trophy mounts and skins from African safaris and hunting trips in the American West and more. The house also boasts a beautiful pool area!

Ernest Hemingway Home and Museum cat

What is cool about visiting the Hemingway Home and Museum is that the property is home to cats that are descendants of Ernest Hemingway’s original pet cats from when he lived in Key West.

A polydactyl cat from the Hemingway Home and Museum in Key West

There are 60 polydactyl cats on the property. That means that due to genetics these cats have six-toes. Cats normally have five front toes and four back toes. In fact, Hemingway had a white six-toed cat that was given to him by a ship’s captain.

When you visit the Hemingway Home and Museum, I recommend doing a guided tour. It usually takes around 20 to 30 minutes. The museum is open every day from 9am to 5pm and tickets cost $17 USD for adults over 12 years old; $7 USD for children ages 6 to 12 and it is free for children 5 and younger.

Walk through the Key West Botanical Garden:
Key West Tropical Forest and Botanical Garden

Known as the only frost-free, subtropical forest and botanical garden in the continental United States, the Key West Botanical Garden Society, Inc. is an educational tropical forest that is worth adding to your Florida Keys road trip itinerary.

During a visit to the Key West Tropical Forest and Botanical Garden, you can explore 15 acres of native gardens and forest. You can also admire all the beautiful native plants in bloom and see beautiful birds and butterflies.

Enjoy Lunch on Sunset Key:

Sunset Key off of Key West, Florida

One of the top things to do during a road trip from Miami to the Key islands, is to enjoy a nice lunch at Latitudes on Sunset Key.

Overall, Sunset Key is a small island off Key West that features upscale cottages and a luxury hotel – Sunset Key Cottages. The only way to get to this island is by having a reservation at Sunset Key’s restaurant – Latitudes or if you’re a resident. You can only get to the island by boat! For those visiting the restaurant, you can only stay at the restaurant and not wonder off.

Latitudes Restaurant on Sunset Key in Key West

Since you must get to Sunset Key by boat, I recommend getting to the dock at least 15 minutes before your scheduled reservation at the restaurant. (The dock is in front of Opal Key Resort.) The boat that goes to and from Sunset Key runs quite frequently during the day and in the evening if you want to enjoy dinner at Latitudes.

If you’re looking for award-winning fine dining and island elegance, then Latitudes is a place you must not miss out on. Both the indoor and outdoor dining areas are stunning and the food and drinks are delicious.

Enjoying lunch and key lime drinks at Latitudes in Sunset Key on a Florida Keys road trip itinerary

During our afternoon at Latitudes on Sunset Key, I had the ahi tuna sliders that came with wakame, pickled ginger and wasabi. Caitlin had the harvest salad with yellowtail snapper. The drinks we enjoyed with our meals were the key lime martini and key lime colada. We were also lucky to get seating overlooking Sunset Key’s beautiful beach!

You can visit Latitudes on Sunset Key for breakfast, lunch or dinner!

Wine Taste on a Sunset Sail:

A woman enjoying a Wind & Wine Sunset Sail in Key West during a Florida Keys road trip itinerary

Another epic activity that you must do on a Florida Keys road trip itinerary is a sunset sail on the Gulf of Mexico! The sunsets in Key West, Florida are some to remember and one of the best experiences I had during my trip was enjoying a beautiful sunset wine tasting sail along the Gulf of Mexico with Danger Charters.

A sunset and wine sail during a Florida Keys road trip itinerary

Being on a sailboat is always a special experience for me, no matter where I am, but being able to enjoy it in “America’s Caribbean” was even more fun. The weather was gorgeous, there were other sailboats out in the horizon, palm trees swayed from nearby islands and there was happiness all around. (I also got to do similar sailing experiences during my summer getaway to Newport, Rhode Island in 2020 and also in NYC during summer 2021.)

A woman enjoying a sunset sail with Danger Charters

During our Wind & Wine Sunset Sail with Danger Charters, Caitlin and I tasted fine wines ranging from whites, reds, rosés and champagne. There was also delicious hor d’oeuvres to enjoy. If you’re not a wine lover, you can also have craft beer and hard seltzers on the boat.

Sunset sail in Key West

This experience is rated one of the top unique things to do in Florida and you will have a memorable experience. Please make sure to bring a sweatshirt or light jacket with you because it does get chilly on the water in the evening.

Hit Up the Bars and Have Dinner on Duval Street:

Green Parrot Bar on Duval Street in Key West during a Florida Keys road trip itinerary

After your sunset cruise, head back to Duval Street for dinner and drinks! I recommend enjoying dinner at Grand Café on Duval Street.

This New American restaurant has both indoor, porch and lawn seating and there are also fire pits to enjoy with drinks! For your meal, you can savor delicious seafood dishes, pastas, salads and meat plates. There is also a great wine and cocktail menu!

Two iconic bars on Duval Street that you cannot miss out on are Sloppy Joe’s Bar and Green Parrot Bar, which is known as the first and last bar on U.S. 1, since 1890. At both bars you can enjoy great drinks and awesome live music!

Day 3:

Venture around Dry Tortugas National Park:

A day trip to Dry Tortugas National Park during a Florida Keys road trip itinerary

Even though we didn’t get a chance to go during our Florida road trip itinerary, I highly suggest doing a day trip to Dry Tortugas National Park. It is known as the USA’s least-visited National Park and it is a place that you must go if you love both water adventures and history.

Dry Tortugas National Park is situated 70 miles west of Key West. The best ways to get there is by ferry, private charter, boat/yacht or seaplane. It will take around two and a half hours to get to the National Park from Key West by boat and over a half hour by seaplane. There are incredible coral reefs to explore, including shipwrecks along with stunning beaches and sand bars to relax at.

The most iconic spot at Dry Tortugas National Park is Fort Jefferson. It is an unfinished coastal fortress and the largest brick masonry structure in the Americas. After Spain sold Florida to the United States, U.S. Navy Commodore David Porter was looking at the fort as a naval station to help suppress piracy in the Caribbean. He was unimpressed with the site and thought it was unfit for the job.

Visiting Dry Tortugas National Park from Key West, Florida

Instead, the U.S. government thought the area was a great location for a lighthouse to guide ships around the reefs. The construction of the now Fort Jefferson was built in the mid 1800s so that the lighthouse and keeper’s cottage were contained within the walls of the fort.

Throughout the Civil War, Fort Jefferson was used as a prison. In fact, it housed four men who were convicted in the plot to kill Lincoln.

During a day trip to Dry Tortugas National Park, you can do a guided tour of Fort Jefferson or you can explore it on your own. To enter into the National Park, it costs $15 USD and it also costs $15 USD to camp there too.

Also on a day trip to Dry Tortugas National Park on a Florida Keys road trip, you can do some epic snorkeling in the coral reefs and around the actual fort. If you are PADI certified, you can Scuba dive at the famous wreck of Windjammer, which is an iron-hilled ship known as the Avanti.

Please note that you must bring your own swimming, snorkeling, Scuba diving and camping equipment to Dry Tortugas National Park.

Before you begin your day, I recommend grabbing breakfast at either your hotel or at Cuban Coffee Queen, which has some of the best Cuban coffee in the Florida Keys. You can also grab a quick to-go Cuban sandwich, smoothie or even a key lime pie!

After your day trip to Dry Tortugas National Park, I suggest grabbing dinner at Mangia Mangia. It is a great Italian restaurant where you can enjoy seafood dishes, fresh pastas with homemade sauce and more.

Fort Zachary Taylor Historic State Park in Key West during a Florida Keys road trip itinerary

If you don’t visit Dry Tortugas National Park, I suggest touring and relaxing at the beach at Fort Zachary Taylor Historic State Park. This National Historic Monument houses the largest cache of Civil War armament in the world. It is also the southernmost State Park in the continental U.S. In addition, Fort Zachary Taylor Historic State Park boasts one of the best beaches in Key West!

Some other great things to do at Fort Zachary Taylor Historic State Park is to hike the Tropical Hammock Trail, snorkel, Scuba dive, bike ride and, of course, relax. It costs $6 USD per vehicle, $2.50 USD for pedestrians, bicyclists, etc. and $4.50 per single-occupant vehicle or motorcycle.

Make Your Way to Isla Bella Beach Resort in Marathon:

Isla Bella Resort during sunset

Once you have dinner and fuel up, drive an hour north to Isla Bella Beach Resort in Marathon, Florida. During your Florida Keys road trip itinerary, you will at some point drive along the iconic Seven Mile Bridge. It is cool to drive over this bridge and Isla Bella Beach Resort is located right next to it!

Isla Bella Beach Resort

Isla Bella Beach Resort is the sister property to Oceans Edge Key West. I loved how stunning this luxury resort features an oasis of contemporary glamour and overall dreaminess. There are five pools, a sandy beach, a Polynesian restaurant, poolside and beach bars, a marketplace café and more!

When we first checked into Isla Bella Beach Resort, we were greeted with a glass of champagne and a cheese and fruit platter.

Isla Bella Beach Resort in Florida

During our stay at Isla Bella Beach Resort, Caitlin and I stayed in the Luxe Beachside Oceanfront 2-Bedroom, 2 Bathroom Veranda. The main room had two queen beds, a spacious en-suite bathroom with a rain shower along with a separate room with a king bed and another en-suite bathroom with a bathtub. (Isla Bella has Molton Brown bath products, which I love!)

Our room also had a gorgeous furnished balcony that overlooked the sea and resort pools. Click here to discover the other rooms and suites at Isla Bella Beach Resort.

Day 4:

Relax at Isla Bella Beach Resort:

A woman staying at Isla Bella Beach Resort during a Florida Keys road trip itinerary

Our last full day of our Florida Keys road trip itinerary was spent relaxing at Isla Bella Beach Resort and enjoying all of the amenities. During a Florida vacation, I believe you need to spend at least one full day relaxing by the beach or poolside and that is exactly what Caitlin and I did.

Begin the Day at The Marketplace at Isla Bella:
Isla Bella Beach Resort Marketplace

We first started our day by grabbing breakfast at the Marketplace at Isla Bella. Open from 7am to 7pm, the Marketplace is a great spot to grab coffee, smoothies, fresh fruit juices, pastries, breakfast sandwiches, salads, paninis and even gelato.

The Marketplace at Isla Bella is also a nice spot to purchase beautiful chic beachwear, home décor, jewelry, souvenirs, skincare products and to also stock up on gear for an outdoor adventure. It is amazing!

In addition to being an eatery and store, the Marketplace also boasts Isla Bella’s Activities Center Concierge where you can book an excursion and rent bikes, gear for snorkeling, kayaks, jet skis and more.

The Florida Keys Seven Mile Bridge during a road trip itinerary

What is cool is that since the resort is located next to the famous Seven Mile Bridge, Isla Bella Resort will host a fun and educational guided run on the pedestrian side every Saturday at 7:45am. Isla Bella will provide everyone with backpacks, water and t-shirts. In total, it is a 4.5-mile run.

Sunbathing at the Pool and Beach at Isla Bella Beach Resort:
A woman staying at Isla Bella Beach Resort in Marathon on a Florida Keys road trip itinerary

During our relaxing last day at Isla Bella Beach Resort, Caitlin and I relaxed at all the pools and beach. There is a main pool that is in the shape of a clover. This pool is the largest and where you’ll find the most people. The other four square pools at the resort are more quiet and less crowded.

Isla Bella Beach Resort

There is one pool that is catered to adults only, which is 18 and older. This is a great pool for those looking for ultimate peace and quiet! At both the main pool and adults-only pool there is a poolside bar to enjoy drinks and light bites. All the pools have comfortable lounge seating and towels you can borrow.

A woman relaxing n a Florida Keys road trip itinerary

Isla Bella Beach Resort also has a beach with lounge chairs to relax at. The views are beautiful! There is also a beach bar to enjoy as well. You can savor freshly caught seafood, from marina to menu, and sip on tropical cocktails.

Ahi tuna poke nachos from Isla Bella Beach Resort
Margaritas on a Florida girl's trip

While we were enjoying the beach and pools, I savored the delicious tuna poke nachos for lunch with plantain chips, ponzu sauce, wakame and key lime wasabi sauce. It was amazing! Caitlin had one of the sushi rolls and enjoyed it too. We both had margaritas to cool off to and it was refreshing!

A woman relaxing at Isla Bella Beach Resort during a Florida Keys road trip itinerary

I loved how the property had something for everyone to enjoy from games to the spa. You also will not have a difficult time finding a place to sit down, take a nap, read a book and sunbathe. (Don’t forget to use sunscreen!)

Sunset at Isla Bella in Marathon, Florida

During sunset, you cannot miss out on the gorgeous views at Isla Bella‘s “Sunset Peninsula”! There was a wedding going on during our evening at the resort, but if you have the chance to see the sun go down at this spot, you will not be disappointed. Plus, you may even see a manatee!

Eating at Mahina:
Isla Bella Beach Resort in Marathon, Florida

The main restaurant at Isla Bella, that I recommend you check out, even if you’re not staying at the resort, is Mahina. This Hawaiian-inspired restaurant features al fresco dining either indoors or at an oceanside table or on the outdoor patio. I loved how dreamy and romantic dining at Mahina was. It is the best place to dine on a honeymoon, anniversary trip, romantic getaway, etc.

Mahina is also a fun spot to enjoy with friends! What is nice is that it is right next to The Beach Bar at Isla Bella Beach Resort, so you can enjoy the live music and fun atmosphere as you savor a nice meal and drink. During our last evening, Caitlin and I enjoyed a lovely Polynesian dinner at Mahina and everything exceeded our expectations!

A Polynesian dinner at Isla Bella's Mahina restaurant during a Florida Keys road trip itinerary

I had the misoyaki salmon, which consisted of white miso, mirin, cane sugar, soy sauce, baby bok choy, squid ink pasta, citrus ponzu sauce and tobiko. Caitlin enjoyed the furikake ahi tuna, which included furikake, coconut forbidden rice, vegetables, wasabi butter, kabayaki sauce and pickled baby ginger.

For drinks, I had the tiramisu martini and Caitlin had the “Mule It Over” cocktail that consisted of Tito’s vodka, limoncello, fresh strawberry, basil and ginger beer. We both shared the flourless chocolate cake for dessert.

The Beach Bar at Isla Bella Beach Resort in the Florida Keys

After dinner, we hung out by the fire pits at The Beach Bar and enjoyed the fun ambiance all around!

Day 5:

Head Back to Miami:

A Florida vacation

The fifth day of your Florida Keys road trip itinerary will have you driving back to Miami. If you want to plan a trip to the Florida Keys and extend your vacation by a few extra days, I recommend heading back up to the city and enjoying the 10 best things to do in Miami, from its beautiful beaches to the fascinating art scene.


A woman sipping champagne during her Florida Keys road trip itinerary

I hope you all enjoyed discovering the best Florida Keys road trip itinerary and reading about my experience in Key West. If you have any questions, please email me at [email protected]

Basic Facts of the United States:

Currency: United States Dollar, Capital: Washington D.C., FL State Capital: Tallahassee, Time Zone: Most of Florida, including the Keys, is on Eastern Standard Time, but anything west of Tallahassee is on Central Standard Time

*Anything could happen during your travels. Always make sure you are insured in case there are unforeseen circumstances such as lost luggage/theft, natural disasters, personal liabilities and more. Click here to get insured for your next trip.

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5 Comments

  1. Kim Deer on February 26, 2022 at 5:45 pm

    Wow, awesome blog on beautiful Key West~ The hotels you stayed at had breathtaking landscapes ~ the homes and Old Town looked so beautiful ~ looks like there are so many fun activities to participate in. The color of the water is amazing ~ so clear and what a fabulous color ~ aqua blue! Definitely on my bucket list. Maybe even a proposed place to retire at~ another awesome read ~ love all your photography too! Love you, mom xoxo 👩

  2. Lucille Pittard on March 26, 2022 at 10:09 am

    Hello.
    I just booked a pre-Memorial Day weekend stay at the IslaBella and stumbled upon your blog.
    I’m an avid traveler and am always looking for a new place to lay my head.
    May alone will take me to Chi’town to experience a bit of the Ton w/ fellow Bridgerton peeps followed by a trip to the Amalfi Coast in Italy. Marathon will see me wrap up the month w/ my best guy.
    I love your writing style and pictures. Very inviting while not overwhelming. I think you have a new follower and fan-girl senior.
    So, thank you.
    Happy travels.
    Lu

    • Taylor Deer on March 29, 2022 at 4:49 pm

      Thank you so much Lucille! You’re going to have a wonderful time at Isla Bella. It is a beautiful resort and I loved the restaurant and pools there. 🙂 Enjoy your trips to Chicago and Amalfi as well. I visited Amalfi Coast for the first time last summer and it was absolutely beautiful.

  3. Lake Toba on May 17, 2022 at 6:41 pm

    What an amazing guide and tips, also all your photos looks so stunning, lvoe your blog so much!

    • Taylor Deer on May 19, 2022 at 3:10 pm

      Thank you so much! 🙂

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Taylor-Key-West1

A Conch Home in Key West, Florida

Commonly referred to as America’s Caribbean, the Florida Keys are a string of tropical islands that stretch over 120 miles off mainland USA, between the Atlantic Ocean and Gulf of Mexico. If you’re a lover of the beach, warm weather, boating, snorkeling and Southern culture, then you must visit the Florida Keys and follow this road trip itinerary!

From north to south, the Florida Keys consist of Key Largo, Islamorada, Marathon, The Lower Keys and Key West. Whether you are someone who enjoys relaxing at a resort pool or beach; exploring our underwater world through Scuba diving or snorkeling; loves a good party; likes to fish or prefers to be on the water, there is something for everyone in the Florida Keys.

A woman touring the Hemingway House during a Florida Keys road trip itinerary

During February 2022, I did a wonderful Miami to Key West road trip with Caitlin of My Darling Passport. After spending a night in the Miami area visiting family, I picked up Caitlin at the airport and we drove to Key West together. It takes around three and a half to over four hours to drive from Miami to Key West. Our Florida Keys road trip itinerary first started with us exploring in and around Key West and we ended our trip relaxing in Marathon.

In this travel blog, discover the best Florida Keys itinerary for 4 days and read all about where we stayed in both Key West and Marathon during our girl’s trip.

**Please note that this blog post uses affiliate links meaning that if you make a purchase via my affiliate link, I receive a small commission at no additional cost to you. I only promote and talk about products and services that I have used and like. During my time in the Florida Keys, Oceans Edge Resort & Marina hosted me for one night and Isla Bella Beach Resort hosted me for two nights. I also partnered with the Florida Keys tourism board.


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Florida Keys Road Trip Itinerary

Planning a Trip to the Florida Keys:

Isla Bella Beach Resort in the Florida Keys

If you are planning a trip to the Florida Keys and only want to stay in Key West, I recommend flying to and from Key West International Airport. If you plan to do a Miami to Key West road trip and stop at various spots along the Keys, then I suggest flying into Miami International Airport. You can find affordable flights through Skyscanner.

For those looking to directly follow my Florida Keys road trip itinerary, you will need to rent a car to get around. If you plan to only stay in Key West, you can get around by utilizing public transportation like Uber, Lyft and city taxis. If you are staying at a hotel or resort in Key West, some of them offer a free shuttle service that will take you into the Old Town area and there is also the Duval Loop, which is a bus route that runs from the island’s Atlantic Ocean area to the Gulf section. The Duval Loop runs adjacent to Key West’s famous Duval Street that is lined with bars, restaurants, boutique shops and more. There are 18 stops along the route.

A cinema in Key West, Florida

In addition to the Duval Loop, you can also take Key West’s other forms of public transportation through The Key West Transit that connects throughout the island itself, along with Stock Island. The Lower Keys Shuttle is a great way to get from Old Town Key West to Mile Marker 53.5 in Marathon.

What I did was fly from Newark Airport in New Jersey to Miami International Airport and rented a car from there. I also flew home from Miami as well!

Driving to the Florida Keys from Miami is easy. There is only one highway, which is called Route 1, and during the prime season, the roads can be busy. Caitlin and I visited the Keys during the popular season and hit some traffic on our road trip.

(Click here if you are planning to road trip around the United States and want to rent an RV.)

Best Florida Keys Road Trip Itinerary:

Colorful houses in Key West, Florida

Day 1:

Drive from Miami to Key Largo:

I recommend beginning your Florida Keys road trip itinerary by heading out of Miami earlier in the day. If you’re looking to see as much as possible, then the earlier you leave, the better it is. There is only one highway in the Florida Keys, which is called Route 1, and there are a lot of beautiful spots you aren’t going to want to miss out on.

The first destination you reach when you officially get to the islands is Key Largo. If you are someone who enjoys exploring our underwater world, then you’re going to want to check out John Pennekamp Coral Reef State Park.

John Pennekamp Coral Reef State Park in Key Largo

Known as the first undersea park in the United States, John Pennekamp Coral Reef State Park includes mangrove swamps with coral reefs and an incredible marine life. Please note that when you visit John Pennekamp Coral Reef State Park, you will need to book an organized tour with a guide to participate in the water activities there.

The fun adventures you can choose from at John Pennekamp Coral Reef State Park are snorkeling and Scuba diving tours and a glass bottom boat tour. You can also rent kayaks, paddle boards and power boats. There are also camping, fishing, swimming and picnic areas throughout the park.

Visit Florida Keys Brewing Co. in Islamorada:

Enjoying craft beer from Florida Keys Brewing Co. during a Florida Keys road trip itinerary

As you continue to make your way down the Keys, you will next hit Islamorada. During your Florida Keys road trip itinerary, I recommend grabbing lunch and local craft beer at Florida Keys Brewing Co., located on Route 1.

Overall, Florida Keys Brewing Co. is the Upper Keys’ first microbrewery and it also includes a beer garden, tasting room and a food truck onsite. The entire brewery is colorful and in the beer garden, you can enjoy yard games like giant Jenga, cornhole and hula hoops. You can also listen to live music during your time at this spot.

On Monday through Saturday, you can savor authentic Mexican food from Jalisco Taco Truck and on Sundays, you can enjoy continental cuisine from A Movable Feast.

Relax and Stay at Oceans Edge Resort in Key West:

A woman enjoying the pool area at Oceans Edge Resort on Stock Island in Key West during a Florida Keys road trip itinerary

During our time in Key West, Caitlin and I stayed at Oceans Edge Resort & Marina, which is situated on Stock Island. This luxury resort is laid back and the perfect spot to vacation on Key West.

Oceans Edge Resort is situated on the marina and includes stunning guest rooms and suites, six saltwater pools to enjoy; a restaurant, café, pool bar and in-room dining and fun activities. Overall, it is a quiet haven just outside of Key West’s thriving Old Town.

A woman on vacation in the Florida Keys

When we first arrived in Key West, Caitlin and I checked into Oceans Edge Resort and relaxed by the pool during the afternoon. After a long winter, a nice day out in the sun was well needed!

Staying at Oceans Edge Resort & Marina:
A woman staying at Oceans Edge Resort & Marina during a Florida Keys road trip itinerary

Caitlin and I stayed in the Oceanfront 2 Bedroom Suite at Oceans Edge Resort. It was nice because we were staying in a pod that included two bedrooms, which means that we each got our own separate room and bathroom.

The Ocean View 2 Bedroom Suite includes one balcony king suite that has a king bed, an en-suite bathroom, a balcony that overlooks the marina and a separate seating area. The other room included two queen beds with an en-suite bathroom and a balcony that also overlooks the marina and pool area.

Key lime pie from Key West

When we first arrived, we were greeted with champagne and key lime pie. Savoring this delicious treat on our balconies was perfect! (Key lime pie is a staple to the Keys.)

I love the coastal style of Oceans Edge Resort & Marina. The furniture and décor will boost your mood from the moment you check in. I also love how each room has a balcony, so that you wake up with the ocean breeze in your face.

Click here to discover all the rooms and suites you can choose from at Oceans Edge Resort in Key West.

Amenities at Oceans Edge Resort:
Staying at Oceans Edge Resort & Marina in Key West

As a guest at Oceans Edge Resort there is a convenient and complimentary shuttle that takes you to and from the resort to Key West’s Old Town. It is around a 15-minute drive to get from the resort to the Old Town. The shuttle stops in front of the Waterfront Brewery and departs hourly between 9am to 11pm. It is great not having to worry about driving into downtown and finding parking and Uber/Lyft services can be quite expensive.

Oceans Edge Resort also has a full-service, 165-slip marina that hosts private watercraft, fishing charters and pleasure cruises. There is also a dry-dock facility.

During your Florida Keys road trip itinerary, I recommend checking out the eateries at Oceans Edge Resort. Yellowfin Bar & Kitchen is a seafood restaurant, bar and grill with stunning waterfront views. You can enjoy fresh fish, steak and chicken dishes as well as salads.

Oceans Edge Resort during a Florida Keys road trip itinerary

Oceans Edge Café is a great spot to have breakfast at the resort. You can wake up to fresh Cuban coffee, smoothies, breakfast sandwiches and baked treats. In addition, the poolside menu can be enjoyed throughout the day and it includes refreshing cocktails, peel-and-eat shrimp, jerk chicken, club sandwiches and burgers.

There is also so much fun to be had at Oceans Edge Resort. While you relax poolside, there are also games to enjoy such as giant chess, Connect Four and ping pong. You can also rent kayaks and paddle boards as well as bikes to take around Key West.

The resort also has a Marine Science Eco Experience, which is a one-hour program that educates guests on sea turtles, dolphin echolocation, lionfish, coral reefs and sharks. Complimentary yoga classes are also offered poolside on Tuesdays, Thursdays, Saturdays and Sundays at 8:30am. There are also paddle board fitness classes held on Mondays and Fridays at 8:30am.

Oceans Edge Resort & Marina also has movie nights and live music at Yellowfin Bar & Kitchen from Thursdays through Sundays from 6pm to 9pm. The hotel also is pet friendly and hosts weddings.

Have a Fun Evening in Key West:

Having fun on Duval Street during a Florida Keys road trip itinerary

A Key West road trip itinerary is not complete without having a fun night out on the island’s most historic neighborhoods – Old Town. Filled with fun bars, renowned restaurants and beautiful Conch-styled houses, Old Town Key West is fascinating and filled with a lot of culture. (Key West is also haunted! Click here to book a ghost tour.)

A popular spot in Key West to have fun at is on Duval Street. Similar to New Orleans’ Bourbon Street, Duval Street is the “main drag” in Key West and it is filled with over 200 bars and restaurants. Along Duval Street are also great souvenir and boutique shops.

Key West has lenient open container laws making it perfect for a bachelor and bachelorette party!

Savor a Nice Dinner at Café Sole:
A hogfish dinner at Cafe Sole in Key West, Florida
Lobster bisque from Cafe Sole
Key lime pie from Cafe Sole in Key West

During our first evening in Key West, Caitlin and I got dinner at Café Sole. This modern French-Caribbean restaurant is snuggled in a peaceful and charming neighborhood of Old Town Key West. I loved how dreamy and cozy it is! There is an outdoor terrace that has stringed lights and cozy seating.

Hogfish is the staple fish to the Florida Keys. If you can try hogfish during your time in Key West, I highly recommend it because it is delicious! During our dinner, I savored the hogfish with veggies and rice as my main meal. I also had lobster bisque as an appetizer. Everything was delicious! Caitlin had a salad with the linguine and clams’ dish and loved it as well. We both split the key lime pie as a dessert!

Listen to Live Music at Blue Heaven:
Having fun at Blue Heaven in Key West during a Florida Keys girl's trip

A fun place to enjoy great drinks and live music after dinner is Blue Heaven, located two blocks from Duval Street, on the corner of Petronia and Thomas Streets.

I loved how Blue Heaven has a fun, “Southern backyard” type of vibe, as I like to refer it as. There is a similar spot to Blue Heaven in New Orleans called Bacchanal Wine and I love how there is a lot of outdoor seating, stringed lights everywhere and just a happy ambiance. Also, the margaritas at this spot did not disappoint!

Day 2:

Explore the best Florida Keys Island:

A house decorated for Valentine's Day in Key West

My favorite area of my Florida Keys road trip was definitely Key West! I love the charming houses and neighborhoods, the fun and happy ambiance, the plethora of different restaurants to choose from and the overall culture it boasts.

Wake Up to Breakfast at Banana Café on Duval Street:
Inside Banana Cafe in Key West

One of the best ways to start the day is by grabbing breakfast at Banana Café. This adorable café has a nice rooftop with stringed lights, a patio looking out at Duval Street and a cozy indoor space.

Breakfast at Banana Cafe on Duval Street in Key West

I loved the breakfast we had at Banana Café! We split the Florida Lobster Eggs Benedict that came with butter-poached Florida lobster meat, avocado, two poached eggs with an English muffin and tomato along with key lime hollandaise sauce and breakfast potatoes. The second dish we split for breakfast was the Belgian Banana Foster Waffle with almonds.

Learn the History of Key West:
A Conch Victorian house in Key West, Florida

After breakfast, we walked everything off by exploring the different neighborhoods within the Old Town. There is a lot of history to Key West! It was originally inhabited by the Calusa and Tequesta Indians. The Spanish came to Key West in 1513 and Ponce de Leon was the one to discover the island.

Key West became a U.S. port of entry in 1823. It was destroyed by a fire in 1886 and in the early 1900s, Henry Flagler built his overseas railway to Key West, which was completed in 1912. U.S. Route 1 runs alongside the railway. Key West also became a large military base too.

Key West, Florida

In the early 1800’s, New England natives, Cubans and Bahamians lived in Key West. The colorful homes that you see around the island represent the history from each of those cultures.

The Conch Victorian houses are the most common homes in Key West. Bahamians built them like they were boats, using timber framing. Other popular forms of architecture you’ll find as you explore Key West are Shotgun Houses and Eyebrow Houses.

A Shotgun Home in Key West

Shotgun Houses are common throughout the American South. It is a narrow home that usually has a porch and a lot of character. According to folklore, Shotgun Houses got its name because a bullet shot can go through the front door and exit the back door without hitting anything. Eyebrow Houses include side-oriented gable-roofed buildings.

Another cool fact about Key West is that it is located at the southernmost point of the continental U.S. You can visit the Southernmost Point Buoy, which is one of the most iconic landmarks in the Florida Keys.

The Southernmost point Buoy in Key West, Florida

Overall, Key West is only 90 miles to Cuba, making it geographically closer to the country versus mainland Florida and Miami.

One of the best ways to get a great history lesson and tour of Key West is by taking the world-famous Conch Tour Train that takes visitors around the island’s most popular and iconic attractions.

Tour the Ernest Hemingway Home:
Visiting the Ernest Hemingway Home and Museum during a Florida Keys road trip itinerary

Ernest Hemingway was a famous American novelist and writer who was born in 1899 and died in 1961. Hemingway became inspired to visit Key West through artists and writers he met in Paris during the 1920s. He ended up getting to Key West from Havana, Cuba.

Inside the Ernest Hemingway Home in the Florida Keys

One of the best things to do in Key West during a Florida Keys road trip itinerary is to tour the Hemingway Home. It is a Spanish Colonial home that was built in 1851 and Hemingway and his wife purchased the house and renovated it in the early 1930s. It is now a National Historical Landmark.

Touring the Ernest Hemingway house in Key West

During a tour of the Ernest Hemingway Home, you will learn about the famous novelist and his life. As you walk throughout the house, you can see Hemingway’s personal touches such as unique European décor and furniture, antiques, trophy mounts and skins from African safaris and hunting trips in the American West and more. The house also boasts a beautiful pool area!

Ernest Hemingway Home and Museum cat

What is cool about visiting the Hemingway Home and Museum is that the property is home to cats that are descendants of Ernest Hemingway’s original pet cats from when he lived in Key West.

A polydactyl cat from the Hemingway Home and Museum in Key West

There are 60 polydactyl cats on the property. That means that due to genetics these cats have six-toes. Cats normally have five front toes and four back toes. In fact, Hemingway had a white six-toed cat that was given to him by a ship’s captain.

When you visit the Hemingway Home and Museum, I recommend doing a guided tour. It usually takes around 20 to 30 minutes. The museum is open every day from 9am to 5pm and tickets cost $17 USD for adults over 12 years old; $7 USD for children ages 6 to 12 and it is free for children 5 and younger.

Walk through the Key West Botanical Garden:
Key West Tropical Forest and Botanical Garden

Known as the only frost-free, subtropical forest and botanical garden in the continental United States, the Key West Botanical Garden Society, Inc. is an educational tropical forest that is worth adding to your Florida Keys road trip itinerary.

During a visit to the Key West Tropical Forest and Botanical Garden, you can explore 15 acres of native gardens and forest. You can also admire all the beautiful native plants in bloom and see beautiful birds and butterflies.

Enjoy Lunch on Sunset Key:

Sunset Key off of Key West, Florida

One of the top things to do during a road trip from Miami to the Key islands, is to enjoy a nice lunch at Latitudes on Sunset Key.

Overall, Sunset Key is a small island off Key West that features upscale cottages and a luxury hotel – Sunset Key Cottages. The only way to get to this island is by having a reservation at Sunset Key’s restaurant – Latitudes or if you’re a resident. You can only get to the island by boat! For those visiting the restaurant, you can only stay at the restaurant and not wonder off.

Latitudes Restaurant on Sunset Key in Key West

Since you must get to Sunset Key by boat, I recommend getting to the dock at least 15 minutes before your scheduled reservation at the restaurant. (The dock is in front of Opal Key Resort.) The boat that goes to and from Sunset Key runs quite frequently during the day and in the evening if you want to enjoy dinner at Latitudes.

If you’re looking for award-winning fine dining and island elegance, then Latitudes is a place you must not miss out on. Both the indoor and outdoor dining areas are stunning and the food and drinks are delicious.

Enjoying lunch and key lime drinks at Latitudes in Sunset Key on a Florida Keys road trip itinerary

During our afternoon at Latitudes on Sunset Key, I had the ahi tuna sliders that came with wakame, pickled ginger and wasabi. Caitlin had the harvest salad with yellowtail snapper. The drinks we enjoyed with our meals were the key lime martini and key lime colada. We were also lucky to get seating overlooking Sunset Key’s beautiful beach!

You can visit Latitudes on Sunset Key for breakfast, lunch or dinner!

Wine Taste on a Sunset Sail:

A woman enjoying a Wind & Wine Sunset Sail in Key West during a Florida Keys road trip itinerary

Another epic activity that you must do on a Florida Keys road trip itinerary is a sunset sail on the Gulf of Mexico! The sunsets in Key West, Florida are some to remember and one of the best experiences I had during my trip was enjoying a beautiful sunset wine tasting sail along the Gulf of Mexico with Danger Charters.

A sunset and wine sail during a Florida Keys road trip itinerary

Being on a sailboat is always a special experience for me, no matter where I am, but being able to enjoy it in “America’s Caribbean” was even more fun. The weather was gorgeous, there were other sailboats out in the horizon, palm trees swayed from nearby islands and there was happiness all around. (I also got to do similar sailing experiences during my summer getaway to Newport, Rhode Island in 2020 and also in NYC during summer 2021.)

A woman enjoying a sunset sail with Danger Charters

During our Wind & Wine Sunset Sail with Danger Charters, Caitlin and I tasted fine wines ranging from whites, reds, rosés and champagne. There was also delicious hor d’oeuvres to enjoy. If you’re not a wine lover, you can also have craft beer and hard seltzers on the boat.

Sunset sail in Key West

This experience is rated one of the top unique things to do in Florida and you will have a memorable experience. Please make sure to bring a sweatshirt or light jacket with you because it does get chilly on the water in the evening.

Hit Up the Bars and Have Dinner on Duval Street:

Green Parrot Bar on Duval Street in Key West during a Florida Keys road trip itinerary

After your sunset cruise, head back to Duval Street for dinner and drinks! I recommend enjoying dinner at Grand Café on Duval Street.

This New American restaurant has both indoor, porch and lawn seating and there are also fire pits to enjoy with drinks! For your meal, you can savor delicious seafood dishes, pastas, salads and meat plates. There is also a great wine and cocktail menu!

Two iconic bars on Duval Street that you cannot miss out on are Sloppy Joe’s Bar and Green Parrot Bar, which is known as the first and last bar on U.S. 1, since 1890. At both bars you can enjoy great drinks and awesome live music!

Day 3:

Venture around Dry Tortugas National Park:

A day trip to Dry Tortugas National Park during a Florida Keys road trip itinerary

Even though we didn’t get a chance to go during our Florida road trip itinerary, I highly suggest doing a day trip to Dry Tortugas National Park. It is known as the USA’s least-visited National Park and it is a place that you must go if you love both water adventures and history.

Dry Tortugas National Park is situated 70 miles west of Key West. The best ways to get there is by ferry, private charter, boat/yacht or seaplane. It will take around two and a half hours to get to the National Park from Key West by boat and over a half hour by seaplane. There are incredible coral reefs to explore, including shipwrecks along with stunning beaches and sand bars to relax at.

The most iconic spot at Dry Tortugas National Park is Fort Jefferson. It is an unfinished coastal fortress and the largest brick masonry structure in the Americas. After Spain sold Florida to the United States, U.S. Navy Commodore David Porter was looking at the fort as a naval station to help suppress piracy in the Caribbean. He was unimpressed with the site and thought it was unfit for the job.

Visiting Dry Tortugas National Park from Key West, Florida

Instead, the U.S. government thought the area was a great location for a lighthouse to guide ships around the reefs. The construction of the now Fort Jefferson was built in the mid 1800s so that the lighthouse and keeper’s cottage were contained within the walls of the fort.

Throughout the Civil War, Fort Jefferson was used as a prison. In fact, it housed four men who were convicted in the plot to kill Lincoln.

During a day trip to Dry Tortugas National Park, you can do a guided tour of Fort Jefferson or you can explore it on your own. To enter into the National Park, it costs $15 USD and it also costs $15 USD to camp there too.

Also on a day trip to Dry Tortugas National Park on a Florida Keys road trip, you can do some epic snorkeling in the coral reefs and around the actual fort. If you are PADI certified, you can Scuba dive at the famous wreck of Windjammer, which is an iron-hilled ship known as the Avanti.

Please note that you must bring your own swimming, snorkeling, Scuba diving and camping equipment to Dry Tortugas National Park.

Before you begin your day, I recommend grabbing breakfast at either your hotel or at Cuban Coffee Queen, which has some of the best Cuban coffee in the Florida Keys. You can also grab a quick to-go Cuban sandwich, smoothie or even a key lime pie!

After your day trip to Dry Tortugas National Park, I suggest grabbing dinner at Mangia Mangia. It is a great Italian restaurant where you can enjoy seafood dishes, fresh pastas with homemade sauce and more.

Fort Zachary Taylor Historic State Park in Key West during a Florida Keys road trip itinerary

If you don’t visit Dry Tortugas National Park, I suggest touring and relaxing at the beach at Fort Zachary Taylor Historic State Park. This National Historic Monument houses the largest cache of Civil War armament in the world. It is also the southernmost State Park in the continental U.S. In addition, Fort Zachary Taylor Historic State Park boasts one of the best beaches in Key West!

Some other great things to do at Fort Zachary Taylor Historic State Park is to hike the Tropical Hammock Trail, snorkel, Scuba dive, bike ride and, of course, relax. It costs $6 USD per vehicle, $2.50 USD for pedestrians, bicyclists, etc. and $4.50 per single-occupant vehicle or motorcycle.

Make Your Way to Isla Bella Beach Resort in Marathon:

Isla Bella Resort during sunset

Once you have dinner and fuel up, drive an hour north to Isla Bella Beach Resort in Marathon, Florida. During your Florida Keys road trip itinerary, you will at some point drive along the iconic Seven Mile Bridge. It is cool to drive over this bridge and Isla Bella Beach Resort is located right next to it!

Isla Bella Beach Resort

Isla Bella Beach Resort is the sister property to Oceans Edge Key West. I loved how stunning this luxury resort features an oasis of contemporary glamour and overall dreaminess. There are five pools, a sandy beach, a Polynesian restaurant, poolside and beach bars, a marketplace café and more!

When we first checked into Isla Bella Beach Resort, we were greeted with a glass of champagne and a cheese and fruit platter.

Isla Bella Beach Resort in Florida

During our stay at Isla Bella Beach Resort, Caitlin and I stayed in the Luxe Beachside Oceanfront 2-Bedroom, 2 Bathroom Veranda. The main room had two queen beds, a spacious en-suite bathroom with a rain shower along with a separate room with a king bed and another en-suite bathroom with a bathtub. (Isla Bella has Molton Brown bath products, which I love!)

Our room also had a gorgeous furnished balcony that overlooked the sea and resort pools. Click here to discover the other rooms and suites at Isla Bella Beach Resort.

Day 4:

Relax at Isla Bella Beach Resort:

A woman staying at Isla Bella Beach Resort during a Florida Keys road trip itinerary

Our last full day of our Florida Keys road trip itinerary was spent relaxing at Isla Bella Beach Resort and enjoying all of the amenities. During a Florida vacation, I believe you need to spend at least one full day relaxing by the beach or poolside and that is exactly what Caitlin and I did.

Begin the Day at The Marketplace at Isla Bella:
Isla Bella Beach Resort Marketplace

We first started our day by grabbing breakfast at the Marketplace at Isla Bella. Open from 7am to 7pm, the Marketplace is a great spot to grab coffee, smoothies, fresh fruit juices, pastries, breakfast sandwiches, salads, paninis and even gelato.

The Marketplace at Isla Bella is also a nice spot to purchase beautiful chic beachwear, home décor, jewelry, souvenirs, skincare products and to also stock up on gear for an outdoor adventure. It is amazing!

In addition to being an eatery and store, the Marketplace also boasts Isla Bella’s Activities Center Concierge where you can book an excursion and rent bikes, gear for snorkeling, kayaks, jet skis and more.

The Florida Keys Seven Mile Bridge during a road trip itinerary

What is cool is that since the resort is located next to the famous Seven Mile Bridge, Isla Bella Resort will host a fun and educational guided run on the pedestrian side every Saturday at 7:45am. Isla Bella will provide everyone with backpacks, water and t-shirts. In total, it is a 4.5-mile run.

Sunbathing at the Pool and Beach at Isla Bella Beach Resort:
A woman staying at Isla Bella Beach Resort in Marathon on a Florida Keys road trip itinerary

During our relaxing last day at Isla Bella Beach Resort, Caitlin and I relaxed at all the pools and beach. There is a main pool that is in the shape of a clover. This pool is the largest and where you’ll find the most people. The other four square pools at the resort are more quiet and less crowded.

Isla Bella Beach Resort

There is one pool that is catered to adults only, which is 18 and older. This is a great pool for those looking for ultimate peace and quiet! At both the main pool and adults-only pool there is a poolside bar to enjoy drinks and light bites. All the pools have comfortable lounge seating and towels you can borrow.

A woman relaxing n a Florida Keys road trip itinerary

Isla Bella Beach Resort also has a beach with lounge chairs to relax at. The views are beautiful! There is also a beach bar to enjoy as well. You can savor freshly caught seafood, from marina to menu, and sip on tropical cocktails.

Ahi tuna poke nachos from Isla Bella Beach Resort
Margaritas on a Florida girl's trip

While we were enjoying the beach and pools, I savored the delicious tuna poke nachos for lunch with plantain chips, ponzu sauce, wakame and key lime wasabi sauce. It was amazing! Caitlin had one of the sushi rolls and enjoyed it too. We both had margaritas to cool off to and it was refreshing!

A woman relaxing at Isla Bella Beach Resort during a Florida Keys road trip itinerary

I loved how the property had something for everyone to enjoy from games to the spa. You also will not have a difficult time finding a place to sit down, take a nap, read a book and sunbathe. (Don’t forget to use sunscreen!)

Sunset at Isla Bella in Marathon, Florida

During sunset, you cannot miss out on the gorgeous views at Isla Bella‘s “Sunset Peninsula”! There was a wedding going on during our evening at the resort, but if you have the chance to see the sun go down at this spot, you will not be disappointed. Plus, you may even see a manatee!

Eating at Mahina:
Isla Bella Beach Resort in Marathon, Florida

The main restaurant at Isla Bella, that I recommend you check out, even if you’re not staying at the resort, is Mahina. This Hawaiian-inspired restaurant features al fresco dining either indoors or at an oceanside table or on the outdoor patio. I loved how dreamy and romantic dining at Mahina was. It is the best place to dine on a honeymoon, anniversary trip, romantic getaway, etc.

Mahina is also a fun spot to enjoy with friends! What is nice is that it is right next to The Beach Bar at Isla Bella Beach Resort, so you can enjoy the live music and fun atmosphere as you savor a nice meal and drink. During our last evening, Caitlin and I enjoyed a lovely Polynesian dinner at Mahina and everything exceeded our expectations!

A Polynesian dinner at Isla Bella's Mahina restaurant during a Florida Keys road trip itinerary

I had the misoyaki salmon, which consisted of white miso, mirin, cane sugar, soy sauce, baby bok choy, squid ink pasta, citrus ponzu sauce and tobiko. Caitlin enjoyed the furikake ahi tuna, which included furikake, coconut forbidden rice, vegetables, wasabi butter, kabayaki sauce and pickled baby ginger.

For drinks, I had the tiramisu martini and Caitlin had the “Mule It Over” cocktail that consisted of Tito’s vodka, limoncello, fresh strawberry, basil and ginger beer. We both shared the flourless chocolate cake for dessert.

The Beach Bar at Isla Bella Beach Resort in the Florida Keys

After dinner, we hung out by the fire pits at The Beach Bar and enjoyed the fun ambiance all around!

Day 5:

Head Back to Miami:

A Florida vacation

The fifth day of your Florida Keys road trip itinerary will have you driving back to Miami. If you want to plan a trip to the Florida Keys and extend your vacation by a few extra days, I recommend heading back up to the city and enjoying the 10 best things to do in Miami, from its beautiful beaches to the fascinating art scene.


A woman sipping champagne during her Florida Keys road trip itinerary

I hope you all enjoyed discovering the best Florida Keys road trip itinerary and reading about my experience in Key West. If you have any questions, please email me at [email protected]

Basic Facts of the United States:

Currency: United States Dollar, Capital: Washington D.C., FL State Capital: Tallahassee, Time Zone: Most of Florida, including the Keys, is on Eastern Standard Time, but anything west of Tallahassee is on Central Standard Time

*Anything could happen during your travels. Always make sure you are insured in case there are unforeseen circumstances such as lost luggage/theft, natural disasters, personal liabilities and more. Click here to get insured for your next trip.

Shop my Key West Look:

Click here to shop my Poshmark closet!

5 Comments

  1. Kim Deer on February 26, 2022 at 5:45 pm

    Wow, awesome blog on beautiful Key West~ The hotels you stayed at had breathtaking landscapes ~ the homes and Old Town looked so beautiful ~ looks like there are so many fun activities to participate in. The color of the water is amazing ~ so clear and what a fabulous color ~ aqua blue! Definitely on my bucket list. Maybe even a proposed place to retire at~ another awesome read ~ love all your photography too! Love you, mom xoxo 👩

  2. Lucille Pittard on March 26, 2022 at 10:09 am

    Hello.
    I just booked a pre-Memorial Day weekend stay at the IslaBella and stumbled upon your blog.
    I’m an avid traveler and am always looking for a new place to lay my head.
    May alone will take me to Chi’town to experience a bit of the Ton w/ fellow Bridgerton peeps followed by a trip to the Amalfi Coast in Italy. Marathon will see me wrap up the month w/ my best guy.
    I love your writing style and pictures. Very inviting while not overwhelming. I think you have a new follower and fan-girl senior.
    So, thank you.
    Happy travels.
    Lu

    • Taylor Deer on March 29, 2022 at 4:49 pm

      Thank you so much Lucille! You’re going to have a wonderful time at Isla Bella. It is a beautiful resort and I loved the restaurant and pools there. 🙂 Enjoy your trips to Chicago and Amalfi as well. I visited Amalfi Coast for the first time last summer and it was absolutely beautiful.

  3. Lake Toba on May 17, 2022 at 6:41 pm

    What an amazing guide and tips, also all your photos looks so stunning, lvoe your blog so much!

    • Taylor Deer on May 19, 2022 at 3:10 pm

      Thank you so much! 🙂

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