Driving around Florida is arguably the best and only way to truly see the Sunshine State and is, in my opinion, one of the best trips for your first visit to the United States. It is amazing to think that Florida is larger than many countries. With its amazing wildlife and conservation area, incredible beaches, and happening cities, Florida road trip destinations are sure to enable the trip of a lifetime.
While you can see a lot hitchhiking around the state, a fun itinerary for a great road trip in Florida sets the pace for a more relaxed holiday with guaranteed attractions. It’ll help you to see some of the most unique sights, both natural and manmade, around the Sunshine State.
Below is a guide on how to organize your Florida road trip for 2 weeks, where to stay, where to stop, what to see, and many other tips to ensure an unforgettable 14 days in Florida. You’ll also learn about some of the best things to do in Miami.
Getting to Florida
If you’re within the United States already, you can either fly to Orlando or drive there if you’re in a state close by. If you’re outside the United States, you can look out for cheap flights to Orlando by searching on Skyscanner.
You can also create a Google Flight alert or sign up to The Points Guy or Scotts Cheap Flights as their newsletters often list the best flight deals. Check out this post to see the airports closest to Anna Maria Island.
Applying for a Visa
One of the most important things to do before any trip to the United States is to look up if you need a visa or not and be sure to apply well in advance. The US is known to be very strict, and you simply will not be allowed to board your flight to the United States without proof of a tourist visa.
Being from Ireland, I had to apply for ESTA – this is a mandatory travel authorization that allows me (and many other nationalities) to travel to the USA without a US visa. It’s quick and easy to apply online, and should not take more than a few days to be approved.
You can find more information about what the ESTA visa is here, so there is no confusion.
To find out of your country is eligible for ESTA and thus visa-free travel to the USA, look at the full list here.
Florida Road Trip Days 1 – 3: Arriving in Orlando
Orlando is a trip in and of itself, but with a huge airport and more car rental options than you can imagine. I chose to begin this wonderful journey here. Almost everyone comes to Orlando for the theme parks.
For thrill-seekers, this is absolute heaven for your Florida trip itinerary. Depending on what you fancy, you can spend the day exploring Harry Potter World at Universal Studios (as well as enjoying a bunch of rides while you’re there). Otherwise, feel the excitement of meeting Mickey Mouse for the first time at Disney World — you can grab your entrance tickets in advance here.
Orlando is also a great place to shop — there are a plethora of outlets and shopping malls unless you’d rather spend the day with the whales at Sealife Orlando with an entry ticket. There is something for everyone to do in Orlando. This is why I recommend a good three days spent here out of your 2 week road trip.
If you want a less obvious experience in Florida, I would head over to Gatorland. The real O.G. of theme parks, Floridians love to call this the Original Theme Park in Orlando. It’s practically impossible to go on a trip to Florida without going gator-spotting or encountering one in the wild. So it’s best to come here and learn life-saving tips and techniques in case you encounter one. There are 1.25 million alligators around, so the chance of meeting one (or at least seeing one) is high.
Tip: Get a hotel with a shuttle to and from the parks, a perk that most offer for free. This will save you on gas and parking! 
Where to Stay in Orlando
While Orlando offers a lot more than the theme parks, I would suggest staying close to them. It saves time on travel, plus more time to dip in the pool after a long day exploring in the heat. If you want to splurge, stay directly on Disney or Universal Property.
If you want to stay someplace more economical, any hotel along International Drive will put you dead center in the middle of a bunch of restaurants, bars, and theme parks. There are many budget and mid-range hotels, but also plenty of luxurious options.
On the Way: Blue Spring State Park
The drive to St. Augustine is about 1 hour and 45 minutes, so why not break it up by taking a dip at one of the most beautiful natural springs in Florida? Blue Spring State Park is home to manatees that come to the springs for the consistently warm temperatures. From April until November you can swim, paddleboard, and kayak in this state park with these majestic creatures. It costs only $6 per vehicle and there is camping here if you wish to extend your trip.
Florida Itinerary Day 4 – 5: St Augustine
The first stop is the United States’ oldest city, St. Augustine, settled by the Spanish in 1565. Known for its Spanish Colonial Architecture and the Fountain of Youth, this city will have your heart from the moment you step foot here.
Walk the narrow and gorgeous St. George Street lined with small shops and restaurants, or see the Oldest Wooden School House in North America. Tour the Old Spanish Fort Castillo de San Marcos, and explore the unspoiled beaches of Anastasia Island State Park.
The Castillo De San Marcos National Museum is the highlight of St. Augustine. The Spanish Fort has phenomenal views of the ocean and city.
With such a long history, it’s no wonder there’s a ghost tour available here. If ghouls aren’t your thing, you can swim with the dolphins instead, or attend a pirate cruise complete with an onboard show.
Tip: Old Town Trolley tours allow you to see the city efficiently without breaking a sweat.
Where to Stay in St Augustine?
A few top choices for where to stay.
Economical
Stay in St. Augustine Beach if you want beach culture, nature, camping, bars, and partying. The St. Augustine Beach KOA Campground is the perfect place to park your RV or pitch your tent. With waterfront cabins available, you could also come here without a tent. It’s the perfect spot to get close to nature!
Mid-Range
The Historic District is the perfect place to be in the middle of all the action, with a variety of restaurants, tours, and attractions. You’ll be within walking distance of everything, which is helpful since parking is so hard to find. Check out St. George Inn to stay inside the old city walls.
Luxury
If waking up in the middle of a natural preserve with quiet beaches is your thing, head to Vilano or Ponte Vedra Beach. The Ponte Vedra Inn & Club is a fantastic resort, sublime for golf and beach lovers.
On the Way: Daytona Beach
From St. Augustine take Route 1 or A1A, the twin highway that runs up and down the east coast all the way to Key West. An hour south will take you to Daytona Beach, the self-proclaimed “World’s Most Famous Beach”.
Daytona Beach is famous for being the spring break destination for countless college kids over the years, as well as the home of the Daytona Speedway. Stop here for lunch or a break and literally drive onto the beach for $20 before heading to Cocoa Beach.
Florida Itinerary Day 5 – 6: Cocoa Beach/ Kennedy Space Center
Between Daytona and Cocoa Beach is the famous Space Coast, a 95-mile section of Route 1 that’s home to the Kennedy Space Center. It is a full-day trip to the Kennedy Space Center, which is why I recommend staying in Cocoa Beach for the night.
The Kennedy Space Center is a huge complex and you need ample time to see it all, catch shuttles, and experience everything. From touring the U.S. Astronaut Hall of Fame to seeing the Space Shuttle Atlantis Exhibition and getting nose-to-nose with the last shuttle and flying a NASA mission.
The Pass will set you back $75 for adults and $65 for children, and you can book here in advance. If you fancy a guide and airboat ride, this tour is the one for you. You can even meet a real live astronaut and chat with them in this package. It is an out-of-this-world experience not to be missed during your 2 weeks in Florida. You may even get lucky enough to see one of many SpaceX launches from Kennedy Center or Cocoa Beach.
Cocoa Beach is a surfers paradise, with decent waves and the largest Ron Jon Surf Shop in the world open 24/7. There are a number of amazing spots to suit any road trip around Florida — eat ice cream on Cocoa Beach Pier or go shopping in the Historic Victorian Cocoa Village.
Tip: Stop in Manatee Sanctuary Park. It includes a playground, a boardwalk, and a mile-long walking trail where you can spot manatees gathering during the winter/spring months.
Where to Stay in Cocoa Beach?
A few top choices for where to stay.
Economical
TownePlace Suites at around $116 is close to Kennedy Space Center, the highway, the beach, and in the center of everything. Perfect for the budget traveler.
Mid-Range
Westgate Cocoa Beach Resort is the perfect family-friendly resort. With waterpark features like a lazy river and close proximity to the ocean, there will never be a moment of boredom. Starting at $289 and up.
Luxury
Hilton Cocoa Beach Oceanfront is a full-blown resort located 30 minutes away from Kennedy Space Center. It offers on-site restaurants, a tiki bar, on-site surfing lessons, and a beautiful oceanfront deck. Definitely a splurge at $373, but one of the loveliest hotels in the area.
On the Way: The Breakers at Palm Beach
Listed on the National Register of Historic Places, The Breakers is a hotel full of the grandeur and glitz of South Florida. The railroad tycoon Henry Morrison Flagler developed the property in 1896, basing it on the Italian Renaissance style of Villa Medici from the 1400s.
Head to The Circle for one of the most opulent brunches of your life, or just to take a great picture for your Instagram. This place is a perfect resting spot before heading to Fort Lauderdale.
Day 6 – 7: Fort Lauderdale
Fort Lauderdale is Miami’s young hip sister. Fort Lauderdale Beach is a hidden Florida treasure that’s a must on any Florida road trip itinerary, though many tourists drive by it to get straight to Miami. With a four-mile stretch of sand that is entirely open to the public, it plays host to many great beachside cafés, shops, and equally great nightlife.
Fort Lauderdale is definitely a great place to stop, relax, and soak it all in. It is the perfect time to relax enjoy the beach, roam around the Flamingo Gardens, or traverse the Las Olas Boulevard on one of the many electrical scooters. If the ocean is calling you, take a deep-sea fishing tour or perhaps a pirate cruise.
Also, the culture and arts scenes are blowing up here, so do not forget to stop at Fat Village. Fat Village is a creative enclave, community center, and art gallery, and hosts an incredible art walk. If you happen to be here on the last Saturday of the month, the art walk consists of galleries showcasing local artists, artisans selling gifts, and new exhibits.
There is entertainment and great food here too. While you are here, check out Brew Urban Café, an open-air café that opens up to the train tracks and inspiring street art in the back. A must-do in Fort Lauderdale (or what locals like to call “The Venice of America”) is a boat tour.
There are a few options. You can get a day pass for The Water Taxi that goes through the many canals or take a sightseeing tour with Jungle Queen Riverboats which host tours from 3- 4 hours with entertainment. If you’d rather get a dose of nature, take a ride on an airboat at Sawgrass Park. 
Tip: There are two companies that provide electric scooters in the area and they both require you to download the app. Both Lime and Bird scooters are in the Fort Lauderdale area, and you can unlock the scooters with your smartphone using the app. It makes it easy to see the city/beach because you can stop, pause, and zoom around however you please.
Where to Stay in Fort Lauderdale?
A few top choices for where to stay.
Economical
Hilton Fort Lauderdale Marina is a beautiful hotel that is right on one of the many canals of the Fort Lauderdale Marina. It offers all the necessary amenities and is only a short drive from the beach. Starting at $176, it is well worth the money and works for many budgets on your two-week vacation in Florida.
Mid-Range
Sonesta Fort Lauderdale Beach is newly renovated and laid-back, with sweeping beach views. It is no wonder they won the TripAdvisor Certificate of Excellence. Starting at $209, it is luxurious at half the cost.
Luxury
W Fort Lauderdale has the best rooftop pool in Fort Lauderdale. It is right on the waterfront and is where luxury lounges. Starting at $382 and up, be sure to get the best of the best here.
Florida Road Trip Day 7 – 9: Miami
Miami is much more than South Beach, it has a unique Latin flavor and Caribbean feel that makes you feel like you have left the USA during your road trip through Florida. The people and the beaches are beautiful. The city is so extra, just sitting at one of the many cafés along Ocean Drive you could people-watch and see some of the world’s most exotic cars in the world.
Miami has long been known for its nightlife and beaches, but it also has a very rich art and food scene due to its melting pot of cultures. Below I have broken up the three areas that are a must on any trip to Miami on your Florida vacation itinerary.
South Beach/Art Deco District
During the day be sure to walk along South Beach to see the iconic Lifeguard Towers that have become a symbol of the city. All are designed by various artists, architects, and musicians in different colors, sizes, and shapes.
Then head inland to the Art Deco District where you can participate in an Art Deco walk to get a historical background of Miami Beach from an architectural perspective. Catch a celebrity-spottin g cruise to the Venetian Islands or rent a jet ski while you’re there.
Wynwood/Design District
A place to go day or night is the Wynwood and Design District. The Wynwood Walls are in Wynwood and represent galleries and walls that have revolving exhibits of street artists from around the world.
It has recently become famous from Instagrammers around the world snapping up images here. Also not to be missed are the multitude of vintage/secondhand shops, upscale shopping, cafés, and bars that are open till the wee hours of the morning.
Little Havana
The Cuban American neighborhood is my favorite place to go for food. You cannot say you have been to Miami without having tried a Cuban Sandwich with a Cubano coffee. The best restaurant in my opinion to get Cuban food is Versailles. Be sure to stop by the Máximo Gómez Park to watch locals play Dominoes, an enduring tradition. Maybe stick around for a salsa lesson or two!
Tip: Miami offers many free museums and art galleries that are perfect for rainy days. The Institute of Contemporary Art is always free and in the Design District and is the perfect escape from the often overwhelming South Beach Neighborhood.
Where to Stay in Miami?
A few top choices for where to stay.
Economical
Generator Miami is an upscale hostel starting at $145. With an on-site restaurant, pool, and air-conditioning, it’s unbeatable. And only a minute’s walk from the beach, too!
Mid-Range
Holiday Inn Miami Beach Oceanfront is one of the many mid-range hotels to choose from, but this one is Oceanfront and not far from the action. Starting at $167, it is a great option for a budget-minded trip to Miami Beach.
Luxury
There is no shortage of luxury options in Miami Beach, but some of the best in my opinion are 1 Hotel South Beach, Loews Miami Beach Hotel, and SLS South Beach. Their prices vary greatly from $299 to $985.
On the Way: Bahia Honda State Park
The park encompasses over 500 acres and is an offshore island that offers some of the best snorkeling in the world. Bahia Honda’s award-winning beaches and historic bridge make it a must-see along the amazing route to Key West from Miami. The park is open from sunup to sundown and costs $8 per vehicle to enter.
Day 9 – 11: Key West
Key West is a well-preserved enclave of Victorian-Era houses and Conch Cottages that surround Duval Street, the center of life on Key West. Allow at least a day if you’ve driven this far to take it all in, and grab the Conch train tour if you can. Whether that means tasting the key lime pie, checking out Hemingway’s House, or checking out the shops, you can experience most of this in a bicycle tour. You can even experience some exhilarating watersports such as parasailing.
When sunset rolls around, head to Mallory Square where it turns into a carnival of street performers and drinks along the pier as everyone waits for the best sunset in the world.
At this point in your 2 week Florida itinerary you’ve made it to the end of Route 1, so take a selfie at mile marker 0 for your scrapbook. It’s also the Southernmost point of the continental USA.
Tip: Book an Airbnb ahead of time if you do not want to pay exorbitant prices on hotels. Ever since Hurricane Irma, prices have skyrocketed. Also, if you want to go to Dry Tortugas National Park, save a whole day for that and be prepared to budget $15 dollars entry fee per person. 
Where to Stay in Key West?
A few top choices for where to stay.
Economical
Not Your Average Hostel is one of two hostels in Key West. It starts at $65 for a 4-bed dorm. This hostel has the amenities of a resort but is still the best place to meet solo travelers.
Mid-Range
Airbnb is where it’s at for nice accommodations at a reasonable price.
Luxury
Casa Marina Key West Waldorf Astoria Luxury is the most luxurious hotel in Key West. Rooms start from $200 in low season to $510 in high season. Established in the 1920s, this place is a gem of itself.
On the Way: Everglades
As you drive across the state to the West Coast on the Tamiami Trail (the highway that connects Miami to Tampa), you will come across two entrances to the Everglades National Park.
The Everglades was originally viewed as a worthless swamp. However, activists such as Marjory Stoneman Douglas showed the world how important the Everglades were for preserving nature for generations to come. Take an airboat ride to see the alligators, wild hogs, and deer on this tour.
Fun fact: The Flamingo Visitors Center at Everglades National Park is the only place to see the American Crocodile.
Day 12 – 13: Sanibel Island
Sanibel Island is a quiet respite and the perfect place to relax before you start wrapping up your road trip. The island’s turquoise waters, pearl white sand, and shells galore will have you thinking you are in a Caribbean Paradise.
Come check out the Flamingos at J.N. Ding Darling Wildlife Refuge. The cost is $10 per vehicle. There is a four-mile wildlife drive that you can bike, hike, or drive around. Just a friendly note that the park is closed on Fridays. Head to see one of Florida’s historic lighthouses and visit Sanibel Lighthouse — it is perfect for sunset.
Tip: Head to Sea Breeze Café where you will have the perfect vistas of the ocean during your breakfast, lunch, or dinner. With Happy Hour from 16:00 -18:00 and Margarita Mondays 18:00 – 20:00, this is the place to be.
Where to Stay in Sanibel Island?
A few top choices for where to stay.
Economical
Kona Kai is a no-frills hotel that has a pool and is not far from the beach. It is great for a night’s stay, though prices have risen in the area and accommodation doesn’t come too cheap.
Mid-Range
Marriott Sanibel Harbour Resort & Spa is in the harbor on the mainland right before the toll bridge, however, it is beautiful and gives you luxury at a reasonable price. The rooms start from $291 and up.
Luxury
Casa Ybel Beach Resort is a beautiful oceanfront resort and makes every part of your experience feel like paradise. Starting from $958 and up.
Day 13- 14: Clearwater Beach/Tampa
After a relaxing time at the beach, it is time to pack up once more to the last destination on your Florida road trip to Tampa. The city was built around Ybor City, the historical immigrant community that included Cubans, Europeans, and Jewish Communities that mainly centered around the cigar-making industry.
Today you can come to learn about the history of Ybor City, have amazing Cuban food at places like the Columbia Restaurant, and see flamenco dancers. While the cigar factories have closed, you can still see locals rolling Cuban cigars from the windows of their stores.
As an up-and-coming city in Florida, there is a lot to do. Whether you want to catch an NHL or NFL game, go to museums like the Museum of Modern Art, or shop in Hyde Park neighborhood, there is something for every type of traveler. If you want to do many things, I recommend getting the Go City Pass. Otherwise, take a trip to the Aquarium or have an adventure at the Busch Gardens.
If the beach is still calling your name, you can drive a half hour to Clearwater Beach, named the #1 Beach in the United States four times in recent years.
Tip: The historical trolley is free. It runs from Downtown to Ybor City, but not as far as the beach.
Where to Stay in Tampa?
A few top choices for where to stay.
Economical
The Barrymore Hotel is the most economical hotel in Tampa City Center with prices starting at $143.
Mid- Range
Embassy Suites by Hilton Tampa Downtown Convention Center is affordable in the city center and a block down from the free trolley. The prices start at $275 and up.
Luxury
Le Meridian Tampa in the Downtown City Center along the water close to the Riverwalk, this former Federal Court House is now an architectural gem. It’s a hotel on the National Register of Historic Places. It is definitely a luxurious option in Tampa.
Last updated on October 2nd, 2023 at 12:33 pm
