2-week roadtrip in Florida - Best Itinerary (2024)

You love white sand beaches and vibrant blue oceans? You are a nature and sunbathing lover? You also are a city dweller? You have two weeks of vacation you don’t know what to do with?This itinerary is made for you!

Go on a sunny road trip and discover Florida‘s gorgeous beaches, iconic cities and astonishing sceneries!

Here is a glimpse of the beautiful experiences awaiting in this 2-week road trip in Florida:

• Discover Wynwood District’s street art in Miami
• Surf on the waves of Cocoa Beach
• See some of the oldest buildings in the US when in Saint Augustine
• Dive into the city’s history in Tampa Bay History Center
• Relax on Sarasota’s beaches
• Enjoy kayak between the islets surrounding the heavenly Sanibel Island
• Watch a beautiful sunset from Naples Pier
• Get to know the alligators from Everglades National Park
• Put your snorkelling gear on an admire the beautiful sea life in Key West

To travel safely and without any worry on your mind, we recommend Chapka Insurance!

Itinerary for the 2-week road trip in Florida

Some practical information before your road trip in Florida

For this itinerary, we recommendrenting a car from Hertz.It’s possible to rent it in one city and return it in another without exorbitant prices and limiting hidden costs.

You want to buy a paper travel guide? We recommend this one! In our opinion, it is the most complete, the most visual and the most up to date!

Need a road map to prepare your itinerary? We recommend this one, the most detailed and the most pleasant to read!

The best period for this 2-week road trip in Florida is between december and march. In this part of the US, it is the best season as the temperatures are perfect, both outside and in the water, and there is no heavy humidity around. More information here.

Contents: 2-week road trip in the US

1- Miami – Stop 1 of the 2-week road trip in Florida
2- Cocoa Beach – Stop 2 of the 2-week road trip in Florida
3- Saint Augustine – Stop 3 of the 2-week road trip in Florida
4- Orlando – Stop 4 of the 2-week road trip in Florida
5- Tampa – Stop 5 of the 2-week road trip in Florida
6- Sarasota – Stop 6 of the 2-week road trip in Florida
7- Sanibel Island – Stop 7 of the 2-week road trip in Florida
8- Naples – Stop 8 of the 2-week road trip in Florida
9- Everglades National Park – Stop 9 of the 2-week road trip in Florida
10- Key West – Stop 10 of the 2-week road trip in Florida

2-week road trip in Florida : step by step

2 days recommended

What to do in Miami?

Sunshine State’s big city, between the buzzing streets and the relaxing beaches, it is the perfect first stop of this 2-week road trip in Florida.

• Miami Beach, the Floridian cliché. Enjoy the seaside resorts, its endless white sand beach and many lifeguard towers. You will also get to appreciate beautiful Art Deco buildings and the mediterranean atmosphere of Lincoln Road. If you like partying, to not miss SoBe.
• Explore Fairchild Tropical Garden, USA’s biggest tropical garden.
• ExploreDowntown Miamiby getting on the aerial Metrorail, it goes through the city center, between modern sky scrapers and Art Deco buildings. And do not forget to go explore Wynwood Art Districtand enjoy the street art.
• Do not leave without seeing theVilla Vizcaya,built in 1912 in an Italian Renaissance style. Step inside and get a refreshing feeling, enjoy its beautiful gardens and statues.

Where to sleep in Miami?

• Mid-range: Ideally located in Miami, discover the Courtyard, a beautiful hotel with a pool, a bistro and a fitness centre. The rooms are modern, spacious and comfortable. It’s a great way to fit in with the city.
• High-end: Get your trip off to a great start by staying in one of the beautiful suites at the Hotel Beaux Arts. The hotel is just incredible, the suites are luxurious and the view is amazing. What we like is the pool, jacuzzi, sauna, basketball court, golf course and virtual bowling alley.

1 day recommended

What to do in Cocoa Beach?

A wild paradise.

• ExploreLori Wilsonpark with its golden sand beach. Follow the coastal trail, winding through an abundant oak and palm tree forest, you’ll feel far from civilisation.
• Whether you are a skilled surfer or not,Cocoa Beachis the best surf post in Florida. Surf the calm but constant waves and enjoy a timeless moment.
• Explore Cocoa Beach Pier, enjoy a gorgeous view of the beach. Take a break and stroll around the shops and restaurants bordering the pier.
• VisitRon Jon Surf Shop, world’s biggest surf shop, open 24/7. It even has aquariums, elevators and water falls!
• Go kayaking around the Thousand Islands and get to see manatees and dolphins in the tropical mangroves.
• Continue your 2-week road trip in Florida in style with a sunset catamaran tour, good times guaranteed!

Where to sleep in Cocoa Beach?

• Mid-range: With its 2 pools, bar and gym, the Best Western Cocoa Beach is a great place to enjoy your stop in Cocoa… The proximity to the beach is a real asset, as is the comfort of the bedding.
• High-end: The Westgate Cocoa Beach Resort offers suites with direct access to the beach, a beach volleyball court and various pools or water play areas for children. There’s plenty to keep kids and adults entertained during your stay.

1 day recommended

What to do in St Augustine?

Florida’s oldest town, it’s the historical stop of this 2-week road trip in Florida.

• Walk through the historical district, between century-old houses and traditional shops.
• Explore USA’s oldest house, theGonzalez Alvarez House, built in 1720. While you’re there, go to the Spanish Military Museum or St Augustine’s History museum and learn about the city. .
• Walk through the oldest school in the country, at 14 St George street. You’ll be guided by a robot in a “Little House on the Prairie” atmosphere.
• You could even explore USA’s oldest prison. Step in the Sherif’s office, the cells and the “maximum security” quarter. To learn all about the secrets of this place, we highly recommend doing a guided tour!

Where to sleep in St Augustine?

• Mid-range: Located in the heart of the city, Villa 1565 welcomes you in a great outdoor setting with its large swimming pool which is very pleasant during the season. The rooms are spacious and comfortable and the breakfast is very varied.
• High-end: In a different style and in the centre of the historic district of Saint Augustine, the St George Inn offers spacious rooms with balcony. The breakfast is top notch and can be taken outside, which makes it even more enjoyable.

2 days recommended

What to do inOrlando?

This step of the 2-week road trip in Florida is the Theme Park Capital of the World,and youinner child will love it for sure!

• Go toInternational Drive, Orlando’s main street and have fun inMr Ripley’s believe it or not, an iconic museum. Discover weird facts and objects from all around the world.
• Get your adrenaline fix in one of the many Disney World amusem*nt parks: the futuristicEpcot Center, the zoological Animal Kingdom or the polarDisney’s Blizzard Beach.
• Go to Universal Studioand enjoy your favorite movies’ atmospheres: from Harry Potter, to The Simpsons and Despicable Me or even Men In Black!
• Enjoy a unforgettable time atDiscovery Cove. Swim with dolphins and walk through a breathtaking setting withabundant vegetation.
• Do not forget to explore Orlando’s city’s center: Church Street Station, an old Railway Station built in 1889. At night, enjoy the sound of music in bars, restaurants, shops, clubs…

Where to sleep in Orlando?

• Mid-range: Close to all the parks, drop your bags at the Grand Hotel Kissimmee and try out the hotel’s pool and gym while you’re there. The rooms are well-designed, modern and the breakfast is good.
• High-end: Next to DisneyWorld Park, discover the Waldorf Astoria, a typically American luxury hotel with an 18-hectare golf course, 2 large pools and a spa. The staff is all the more pleasant and friendly. In short, we love it!

1 day recommended

What to do in Tampa?

The Big Guava.

• ExploreYbor City,Tampa’s historic district. Go visitGonzalez y Martinez Cigar Factoryand see how cigars are made.
• For sea world enthusiasts, go to theFlorida Aquariumand discover hundreds of marine species.
• Go toBusch Gardens, a park weirdly blending nature and thrilling rides.
• Discover Tampa’s history at Tampa Bay History Center. Exhibitions about local Native Americans, agriculture, cattle ranching and cigar industry will let you know everything about the city. It’s one of the most interesting visit of this 2-week road trip in Florida.

Where to sleep in Tampa?

• Mid-range: In the centre of Tampa, choose the Hampton Inn to discover the city in peace. The hotel offers a rental service to easily explore Tampa. The hotel is modern and even has a swimming pool.
• High-end: Go for the ultimate in luxury with the Grand Hyatt Tampa Bay, a greatly-equipped hotel with 2 pools, 3 restaurants and a gym. You’ll enjoy free local transportation and stunning views of the bay.

1 day recommended

What to do in Sarasota?

Florida’s calm side, Sarasota is a less known but still wonderfulstoops this 2-week road trip in Florida.

• Go toRinglingMuseumand learn about traditional circus life, step in Ca’d’zan and admire the beautiful Ringling family mansion.
• Car aficionados, go toSarasota Car Museum, one of the oldest car museum in the world, with over 120 vintage cars. You’ll get to see iconic cars like John Lennon’s Mercedes Roadster or one of the only five station wagonCadillac ever made.
• Enjoy the city’s gorgeous beaches. Go toSiesta Keyfor a family afternoon ; Longboat Key,16 km / 10 mile long golf-beach ; Turtle Keywith its empty beaches where you can camp under a beautiful starry sky.

Where to sleep in Sarasota?

• Mid-range: The Westin Sarasota offers beautiful rooms with stunning harbour and city views. You’ll also find a rooftop pool which is great after spending the day exploring! We love it.
• High-end: Located on Sarasota Bay, the Ritz-Carlton offers the ultimate in luxury: large pools with ocean views, dreamy rooms with picture windows, a full-service spa and a restaurant. Click, book, enjoy!

2 days recommended

What to do in Sanibel Island?

Heaven-like landscapes await in this stop of the 2-week road trip in Florida.

• Walk on the coast and look for over 400 different types of shells, betweenSanibelLighthouse and the North of Captiva.
• Rent a kayak or boat and cruise around the hundreds of small islands surrounding Sanibel. Stop atBoca Grande, a lovely 20th century town or at Pike Islandto explore a reconstitution of an old Native American village.
• Rent a bike and ride along the 22 km / 13.6 miles of paved biking trails around Sanibel.
• If you prefer walking, take theRabbit Road Trailfollowing the canal for 1.5 km / 1 mile or the Bailey Road-Dunes Circle, a 4 km / 2.5 mile trail between vegetation and beautiful houses.
• Lovers, try the local speciality : get married just like in Las Vegas and get a temporary marriage license. You’ll have 60 days to make it official… or not!

Where to sleep on Sanibel Island?

We don’t have any specific accommodation recommendations for Sanibel, but if you do, please let us know in the comments!

1 day recommended

What to do in Naples?

The Floridian west coast gem.

• Walk around the most iconic historic, romantic and touristic place of the city :Naples Pier, a 200 m / 650 feet long pier. It’s a must see of this 2-week road trip in Florida.
• Enjoy the many beaches: the convenient Lowdermilk Beachwith all the facilites ; the funDelnor-Wiggins Pass State Recreation Beachwith its playground ; the 17 km / 10 mile long white sand beachesGordon PasstoSeagate Drive.
• Attend a concert at the « Phil », the Philharmonic Center of the Arts of Naples, one the only place to organize over 400 events a year !
• Go on an adventure for a few hours and go kayaking in the mangroves of Marco Island.

Where to sleep in Naples?

• Mid-range: 15 minutes from the beach and in the centre of town, Naples Park Central is a classic and comfortable hotel with an outdoor pool. All in all, an excellent value for money to enjoy your time in Naples.
• High-end: In the heart of the city, stay in “luxury cabins” as the hotel calls them, while enjoying a heated swimming pool and a gym by opting for the Bellasera Resort. The benefit: the free shuttle service within a 5km radius and the free provision of bicycles.

2 days recommended

What to do in the Everglades?

Largest wild subtropicalregion of the United States.

• Just like in CSI : Miami, get on a airboat and glide around the swamps. To do your tour, we would recommend any of these companies:Captain Mitch’s airboat Tours,Airboat in Everglades, Gator Park Airboat Tours orCaptain Jack’s Airboat Tours.
• Hike or bike on thePins Island, FlamingoandShark Valley trails.
• Observe over 360 bird species, as well as crocodiles and alligators! It is the only stop of this 2-week road trip in Florida where you will encounter such wildlife.

Where to sleep in the Everglades?

• Low-mid-range: In the heart of the Big Cypress National Preserve, put your bags down in one of the “native cabins” offered by the Everglades Chickee Cottage & Bungalow. If you’re looking for an unusual night’s stay during your trip, this is the place to be!
• Mid-range: For a little more comfort, check into one of the comfortable rooms at the Everglades City Motel. The motel is conveniently located right next to Everglades Park.

2 days recommended

What to do in Key West?

The southernmostisland of the United-States, and of this 2-week road trip in Florida.

• Go diving and discover the world’s 3rd largest coral reef. For beautiful diving spots, go to Key West Marine Park.
• Rent kayaks or paddle boards and cruise around a translucent 32°C / 90°F water.
• Admire a wonderful sunset fromMallory Square.
• Go sunbathing on gorgeous beaches:Fort Zachary, a true peaceful heaven ; Higg’s Beachfor a picnic, barbecue or playing some sport ; Simonton Street Beachfor a view over the Gulf of Mexico.
• Take a pic of the iconic Lighthouse, thesouthernmost point in the US, only 140km / 87 miles from Cuba!
• Want to see more about the island’s culture? Go toDuval Street where you’ll find museums and art galleries.
• Literature lover? Go to Hemingway’s house, enjoy the beautiful architecture and gardens, get a tour of the property and get a glimpse of the famous 6-toed cats!

Which activities in Key West?

• Take a boat tour that combines dolphin watching and snorkeling!
• Make room for culture on a guided bike tour. We love it because it’s a great way to see the place in a different way.
• Enjoy a unique experience during this 2 week itinerary in Florida, by going on a schooner tour at sunset. It’s an absolutely magical moment that you will surely remember for a long time!

Where to sleep in Key West?

• Mid-range: The Truman Hotel welcomes you in a cosy and relaxed atmosphere. The ideal place to rest during the last leg of your journey. The bonuses: the swimming pool, the proximity of the beach and the great breakfast. We love it!
• High-end: Well, we love it even more… But you have to take out your wallet! End your trip beautifully by choosing the Key West Villas, with its superb small individual accommodations, very well located, a swimming pool, and the possibility of renting bikes! And we particularly appreciate the kindness of the owners.

Learn more about your road trip to the US…

• You want to know all the information about the country? It’s here.
• To rent a car at the best price, we recommendthis website.
• To book a flight at the best price, we recommendthis website.
• You are looking for a great travel insurancefor your 2-week road trip in Florida?We recommend this one!

Do not hesitate to share your trip with us, we can’t wait to hear all about your adventures!

If you have more information, good deals, or any advice to share about this itinerary, leave a comment below! Our team will be happy to hear about your experiences!