A Tampa to Key West road trip lets you enjoy the best of South Florida. Make acquaintance with sugar-white beaches, one of the best wildlife experiences in America and, at the end of the road, the unique Florida Keys setting.
This Tampa to Key West road trip itinerary comprises three distinctive sections — each one with its own unique charm.
The first section traces Florida’s west coast . As you head south from Tampa, you find one stunning Gulf Coast beach after another. Naples and Marco Island are shining gems on a long list of beach paradises.
Then South Florida’s wilderness takes over. When you cross the peninsula, make the most of Everglades National Park. Either take an airboat ride through the wetland, or put on your hiking boots and hit alligator-lined trails.
For many roadtrippers, a few hours in the Everglades is enough. However, you can easily spend a full day or more exploring the vast expanses of one of the most unique pieces of nature in the USA.
Where Florida’s mainland ends, the outstanding Overseas Highway takes over. Spanning 113 eye-popping miles (182 km) from mainland Florida all the way to Key West, it’s one of those very special drives.
In a unique island setting away from the hustle and bustle, the Florida Keys offers appreciated roadside attractions. Driving the Overseas Highway is on its own a nice experience — but it’s best enjoyed if you stop regularly and have several days at your disposal.
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- Total distance: 426 mi / 686 km
- Total driving time: 8.5 h
1. Tampa
Yee-haw — the Florida Keys call your name, and it’s time to begin the road trip from Tampa to Key West. But if you’re not a Tampa local, enjoy the area’s highlights before cruising south.
Take in historic Ybor City
Ybor City is a Tampa neighborhood with a fascinating story to tell. Crowned by the opening of the world’s at the time largest cigar factory in 1888, this once was the planet’s cigar capital of the world.
Mostly Cuban, Spanish and Italian immigrants lived and worked in Ybor City, producing hundreds of millions hand-rolled cigars annually.
Today, Ybor City’s days as a dominant cigar force are long gone. However, there are still more than 950 historic structures standing — such as businesses, churches, factories and social clubs.
So discover the roots of Ybor City before heading south on the Tampa to Key West drive. Top off the experience with dinner or drinks at the neighborhood’s historic Columbia Restaurant, established in 1905.
Stroll Clearwater’s Pier 60
For some sand between your toes, Clearwater Beach boasts a lovely 2.5 miles (4 km) long beach. Its northern end is quieter, while its southern end tends to get rather crowded.
Towards Clearwater Beach’s southern end, Pier 60 gloriously extends 1,080 feet (329 m) out into the Mexican Gulf. It’s an iconic spot for fun in the sand and sun.
The eye-catching Pier 60 is the centerpiece of Clearwater Beach, where something fun always is going on. From tasty food options to quirky shops, you have all you need within steps at the Florida landmark.
Additional stop: Do you want to break up the drive from Tampa to Naples? If so, Siesta Key is as pristine as a detour gets. Siesta Key features close to 100% pure quartz sand, which makes the Florida island snow white.
2. Naples
- Driving distance: 166 mi / 267 km
- Driving time: 2.5 h
The fun-filled Naples is beautifully positioned on Florida’s Paradise Coast. As you visit on the Tampa to Key West road trip, you get to experience the upscale ambience that the city is so famous for.
Walk upscale Fifth Avenue South
In the downtown area of Naples, also known as Old Naples, you find Fifth Avenue South. It’s a mecca for anyone who wants a slice of the good life.
Fifth Avenue South is lined by upscale restaurants, stylish boutiques and more than a few luxury cars. It’s the crown jewel of Naples that is just filled with extravagancy.
Shopping or dining on Fifth Avenue South is a memorable addition to the road trip from Tampa to Key West.
However, just strolling along Fifth Avenue South is a fun thing to do. It’s a pretty walk, and if you continue all the way down the road, you get to Naples Beach.
Play alongside dolphins at Naples Pier
Naples Pier, located on the picturesque Naples Beach, was built already in 1889 but dutifully guards Naples Beach to this day. The historic landmark juts out 1,000 feet (305 m) into the Gulf of Mexico.
Some things just seem to get better with age, and Naples Pier is one of them. It’s one of the prettiest beach spots on the drive from Tampa to Key West.
Stroll the picturesque Naples Pier, hang out on the soft white sand and dive into the clear blue water. It certainly doesn’t get much better than that.
But some days Naples Pier, in fact, gets even better. Dolphins are frequently sighted here — adding yet another dimension to a beach day in Naples.
Where to stay
Naples hotels in the downtown area give you easy access to the exclusive Naples lifestyle. However, stay further from Naples’ heart if you travel on a budget.
- Hotel Escalante – The best of both worlds.
- Cove Inn – Right on Naples Bay.
3. Marco Island, FL
- Driving distance: 18 mi / 29 km
- Driving time: 0.5 h
On the road trip from Tampa to Key West, you just can’t get enough of pristine beaches. Tucked away in Southwest Florida, Marco Island is another beach paradise to enjoy between Tampa and Key West.
Spend lazy days on South Marco Beach
South Marco Beach covers most of Marco Island’s western shoreline. It’s the biggest of the two public beaches on Marco Island.
With white sand, inviting water and warm year-round weather, South Marco Beach is a quintessential Florida spot. As a bonus, it’s also a nice beach for some shelling on the road trip from Tampa to Key West.
If your batteries aren’t recharged yet, this is the place to finally reach 100% before the Tampa to Key West road trip turns east.
Where to stay
South Beach is the prime location for easy access to the beach. Mid Island and North End you find more hidden Marco Island accommodations a short ride from the dunes.
- JW Marriott Marco Island – Jaw-dropping on the beach.
- The Boat House – Hidden up north.
4. Everglades National Park
- Driving distance: 31 mi / 50 km
- Driving time: 1 h
Not far from the white beaches of Marco Island, the Everglades magnificently spreads out. As you drive right through the Everglades on your way east, it’s a Tampa to Key West chance too good to miss out on.
Tour the wild Everglades
Everglades National Park is the only wetland of its kind in America. The South Florida symbol encompasses an impressive 1.5 million acres of pure wilderness.
To fully discover it, you need to park your car.
Uniquely so, airboat tours take visitors to the heart of the huge wetland. An airboat ride offers both stunning scenery and sightings of curious locals.
The alligator is a Florida legend that often shows up. Other animals within Everglades National Park include crocodiles, manatees and a wide range of tropical birds.
Where to stay
Everglades City, a small city at the Everglades’ western end, is one of the best options for where to stay when visiting Everglades National Park. Here you find the Gulf Coast Visitor Center and several airboat companies that happily take you to the heart of Everglades.
Alternatively, or additionally, approach the Everglades from Ernest Coe Visitor Center across the park. On the park’s eastern side you find several alligator-lined trails, including the popular 0.4 miles (0.6 km) Anhinga Trail.
- Everglades Adventures Hotel – Convenient in Everglades City.
- Fairfield Inn Florida City – Comfy near Ernest Coe.
Additional stop: After having crossed the state of Florida, the bustling Miami is within easy reach. So if you’re hungry for big-city action, add Miami to the itinerary. Otherwise, continue straight south to Key Largo when you have seen what you want of Everglades National Park.
5. Key Largo
- Driving distance: 113 mi / 182 km
- Driving time: 2.5 h
Key Largo is the first major upper island of the Florida Keys. As indicated by its name, the island is at 33 miles (53 km) long the largest segment of the Keys.
In Key Largo the famous Overseas Highway and the Florida Keys adventure begins. Water activities are very appreciated all over the Keys, and Key Largo is certainly no exception.
Enter the Overseas Highway
From Key Largo the Tampa to Key West road trip continues on one of the most spectacular roads in the world, the Overseas Highway.
The Overseas Highway is a breathtaking road that takes you on bridges from key to key until you reach Key West. To enter from the mainland, just head south on US Highway 1 until it becomes the Overseas Highway.
Go underwater at America’s first undersea park
John Pennekamp Coral Reef State Park, located at the start of the Overseas Highway, is known as the first undersea park in the United States. It’s an exciting first Florida Keys stop on the drive from Tampa Bay to Key West.
Home to stunning coral reefs and an impressive marine life, the park really shows how rich the Keys are in natural beauty.
You can explore John Pennekamp’s corals by diving and snorkeling or from a glass-bottom boat. So it’s totally up to you how active you want to be when visiting.
If you don’t want to, you don’t even need to dip your feet in the water when exploring John Pennekamp Coral Reef State Park.
Relax on canals with the African Queen
Another nice way to explore the waters of the Florida Keys and to learn some movie history is by taking the African Queen on the Key Largo canals. This steamboat got famous through the 1951 movie, starring Katherine Hepburn and Humphrey Bogart, with the same name.
An African Queen canal trip is, of course, extra interesting if you have seen the movie. But even if you haven’t seen it, the boat tour is a pleasant stop on the Tampa to Key West itinerary.
Where to stay
You just entered the Overseas Highway, but you still find some quintessential lodging already in Key Largo. Stunning Key Largo resorts show that you don’t need to go deep into the Florida Keys to find some real gems.
- Playa Largo Resort & Spa – A luxury oceanfront resort.
- Sunset Cove Beach Resort – Cozy beachfront lodging.
6. Islamorada
- Driving distance: 17 mi / 27 km
- Driving time: 0.5 h
After a first taste of Florida Keys in Key Largo, the road trip from Tampa Bay to Key West continues further down in the Keys. It’s time to explore the fun things to do in Islamorada.
Islamorada is packed with opportunities to fully take in the beautiful environment of the Florida Keys. The area is known as the sport-fishing capital of the world, and water activities are in abundance.
Explore the forgotten Indian Key
The Indian Key Historic State Park is a unique stop on the drive from Tampa to Key West. The state park is located within sight of the Overseas Highway. However, it’s offshore and only accessible by boat.
Boasting a surprisingly rich past, Indian Key became the first county seat of Dade County in 1836. Wrecking ships was big business, and the first Indian Key inhabitants even wanted to compete with Key West.
In the end it didn’t work out, and a long time has passed since anyone lived on Indian Key. But a visit to the island is both historically interesting and a great chance to see some exceptional marine life on the Tampa to Key West road trip.
Feed fish at Robbie’s
Waterfront in Islamorada, Robbie’s is both a fun and tasty stop on the Tampa to Key West road trip.
Experience wise, people from all around the world go to Robbie’s for the opportunity to feed tarpons. In fact, the place has become an institution along the Overseas Highway.
Massive silver giants wait at Robbie’s dock for food. They love to snatch it right out of your hands — those tarpons certainly aren’t shy when you dangle fish on the surface — and down in their stomachs it goes.
While you’re here, neither miss out on Robbie’s Hungry Tarpon Restaurant and Thirsty Tarpon Bar. No matter if you’re after breakfast, lunch, dinner or cocktails, Robbie’s is a great place to be.
Where to stay
Islamorada is a superb base on the Tampa to Key West road trip. You can’t stay on Indian Key nowadays, but there’s still plenty of tempting Islamorada lodging to choose from.
- Islander Resort – Picturesque with phenomenal landscaping.
- Sands of Islamorada – More simple but comfortable.
7. Marathon
- Driving distance: 30 mi / 48 km
- Driving time: 0.5 h
As you leave Islamorada, you have passed the halfway point between Miami and Key West. In Marathon you’re instead about halfway to Key West from the start of the Overseas Highway.
When the Florida Keys Overseas Railroad was built in the early 1900s, the stakes were high and efforts put in by the workers enormous. They worked day and night to finish the project on schedule.
As they worked, the men said that “this is getting to be a real marathon”. Hence the name for the local station and later city was born.
Relax on sandy Sombrero Beach
It’s almost impossible to not long for a beach to relax on when you, in the endless summer season of Florida Keys, travel from Tampa to Key West. And in Marathon you find one of the most popular beaches in the Florida Keys, Sombrero Beach.
Sombrero Beach appeals with a sandy shoreline, calm waters and palm trees that give shade for when the direct sun feels too strong. Its shallow water is ideal for a day of unwinding, sunbathing, swimming and snorkeling on the Tampa to Key West road trip.
Discover a Florida Keys turtle sanctuary
From April to October it’s nesting season for the Florida Keys’ population of loggerhead turtles. That’s great, but how can you get close to and learn more about them as you drive from Tampa to Key West?
For a beautiful learning experience, head to the Florida Keys Turtle Hospital in Marathon. The turtle hospital rehabilitates injured sea turtles and return them to their natural habitat.
If you book a guided tour, you get to learn everything there’s to know about turtles and the hospital’s efforts to save them. A visit is rewarding both for adults and younger travelers on a Tampa Bay to Key West family road trip.
Where to stay
The heart of Florida Keys is a true island oasis. Marathon has a lot of great places to stay to really make the most of the time in the central Florida Keys area.
- Courtyard by Marriott Marathon – An excellent Marriott.
- Isla Bella Beach Resort & Spa – Exclusive by the Seven Mile Bridge.
Additional stop: The Lower Keys area between Marathon and Key West is refreshingly quiet. To see more of this region, which many visitors just drive through, stop at Bahia Honda State Park, home to a lovely beach overlooking the historic Bahia Honda Rail Bridge. Then tick off the National Key Deer Refuge on Big Pine Key, where the tiny key deer lives and thrives.
8. Key West
- Driving distance: 51 mi / 82 km
- Driving time: 1 h
After a spectacular road trip from Tampa to Key West, you’re finally there. In Key West not only does the Overseas Highway end but also the continental United States.
Let’s make the most of our time in this unique city.
Enter the Hemingway Home
If just one thing to do is mandatory in Key West, it’s probably the Ernest Hemingway Home. Here, on Whitehead Street and surrounded by Key West tranquility, the celebrated American writer and Nobel Prize winner spent a majority of the 1930s.
As you tour Hemingway’s former home and workplace, dotted with descendants of the writer’s own cats, the many colorful stories fascinate you. From the wives, he was married four times, to the of the time cutting-edge swimming pool, there’s so much to indulge in.
Have a good time on Duval
Key West locals with a sense of humor, which includes most of them, say Duval Street is the longest street in the world. After all, it runs from the Gulf of Mexico to the Atlantic Ocean.
But distances aren’t long in the island city Key West. Duval Street is, in fact, just a little over one mile long. However, lined by one quirky attraction after another, one mile is more than enough.
Check out Duval’s many cute souvenir shops, enjoy a slice of key lime pie or sit down at Sloppy Joe’s, once Hemingway’s favorite bar, for one of the most iconic nightlife experiences in America.
Mallory Square, known for its nightly sunset celebration, is located at the northern end of Duval Street. At Duval’s southern conclusion, the family-friendly Butterfly Garden shows that Duval is a street for all ages.
Where to stay
After a scenic Tampa to Key West road trip, it’s nice to not have to rely on your car for a while. From Key West hotels in Old Town you have most attractions and things to do within walking distance.
- Almond Tree Inn – Excellent Key West lodging near Duval Street.
- Blue Marlin Motel – A more inexpensive motel.
Summary of Tampa to Key West drive
That’s it — the ultimate road trip from Tampa to Key West. Let’s have a look at all the great stops, including those additional ones, again.
- Ybor City
- Clearwater Beach
- Siesta Key
- Fifth Avenue South
- Naples Pier
- South Marco Beach
- Everglades National Park
- Miami
- John Pennekamp Coral Reef State Park
- African Queen
- Indian Key Historic State Park
- Robbie’s
- Sombrero Beach
- Florida Keys Turtle Hospital
- Bahia Honda State Park
- National Key Deer Refuge
- Ernest Hemingway Home
- Duval Street
Road trip from Tampa to Key West FAQ
Here you find the answers to some frequently asked questions about the Tampa to Key West road trip.
The ultimate Tampa to Key West road trip is 426 miles (686 km) long. Driving it takes roughly 8.5 hours, not including any stops along the way.
If you just take the quickest route from Tampa to Key West, the distance is the same but with a driving time of 7 hours.
The main stops included on the ultimate Tampa to Key West road trip are Tampa, Naples, Marco Island, Everglades National Park, Key Largo, Islamorada, Marathon and Key West.
Additional Tampa to Key West stops along the route include Siesta Key, Miami and the Lower Keys.
The perfect amount of time for the Tampa to Key West road trip depends on how deeply you want to explore the stops along the way. You can spend weeks exploring everything between Tampa and Key West, or if you don’t mind quick stops, it can be done over only a few days.
Just have in mind that the Overseas Highway, one of the best drives in America, needs time to be appreciated. If you just drive it in one go, you most likely will be disappointed. Therefore make sure that you allow multiple days for the final stretch of the Tampa to Key West road trip.
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