Tampa to Key West: Miami, Overseas Highway & Keys

This epic Florida road trip lets you experience the state from coast to coast, ending in an island paradise. From Tampa, drive south on I-75 about 4 hours to reach Miami. The fastest route cuts across the state from the Gulf to Atlantic via “Alligator Alley” the stretch of I-75 that crosses the Everglades from Naples toward Ft. Lauderdale. Alligator Alley is an 80-mile scenic highway through Everglades marshland where you might literally spot alligators lurking along the canal banks as you drive! (There are a couple of well-marked rest stops along Alligator Alley consider stopping for a quick look; often you can see gators sunning in the water below.) Keep in mind this is a remote section of highway, so fill up on gas and snacks before you enter, and be prepared for a toll.

When you arrive in Miami, you’ll feel the energy immediately. Spend a day or two soaking up Miami’s vibrant culture. South Beach is a must-visit this famous stretch of Ocean Drive is lined with iconic Art Deco architecture and palm-fringed sands. By day, relax on South Beach’s golden sands or stroll the Art Deco Historic District, snapping photos of the pastel-colored 1930s hotels. By night, South Beach transforms into a hotspot for nightlife, with bars and clubs pulsing along Ocean Drive and Collins Avenue. For a taste of Miami’s Latin flair, head to Little Havana. Along Calle Ocho (8th Street), you can savor authentic Cuban food think strong cafecito coffee, Cuban sandwiches, and guava pastries and perhaps catch locals playing dominoes at Máximo Gómez Park. Little Havana’s atmosphere is rich with Cuban heritage; live salsa music and mojitos flow at legendary spots like Ball & Chain, making you feel like you’ve traveled to Havana for an evening. Also take time to explore Wynwood, Miami’s hip arts district. By day, Wynwood is known for its massive outdoor murals (Wynwood Walls) and trendy art galleries. By night, it boasts eclectic bars and craft breweries amid the graffiti-splashed warehouses. It’s the perfect place to enjoy a craft cocktail or local beer while surrounded by colorful street art. Miami’s multicultural, high-energy mix of beaches, art, food, and music will leave a strong impression.

Next, get ready for one of America’s most scenic drives: the Overseas Highway (U.S. 1) down the Florida Keys. Stretching about 113 miles from Miami to Key West, this highway “glides over turquoise waters, connecting 44 islands via endless bridges” a truly unforgettable journey. You’ll hop from key to key on over 40 bridges, including the famous Seven Mile Bridge which offers spectacular views of the Atlantic Ocean on one side and the Gulf of Mexico on the other. Take your time on this drive; it can be done in under 4 hours, but it’s far more rewarding to make it a leisurely all-day or multi-day trip with stops. The water views from the road are so stunning that you’ll want to pause often (there are scenic pull-offs and parks along the way).

As you enter the Upper Keys, your first major stop is Key Largo, the largest and northernmost Key. Key Largo is home to John Pennekamp Coral Reef State Park, the first undersea park in the U.S. If you have time, book a snorkeling tour or a glass-bottom boat ride here to marvel at the vibrant coral reefs just offshore the park’s colorful coral reefs and teeming marine life are accessible by boat tours that run daily. Peering through the glass bottom at tropical fish and coral formations is like entering a giant aquarium. Snorkelers and divers can immerse themselves even more closely among the corals. The reefs of Key Largo (part of the Florida Keys National Marine Sanctuary) are gorgeous and make Key Largo a famous spot for underwater exploration.

Continuing south, about halfway down the Keys you’ll reach Islamorada, known as the “Village of Islands.” A fun pit stop here is Robbie’s Marina at Islamorada. Robbie’s is home of the world-famous tarpon feeding for a few dollars, you get a bucket of fish and walk out onto the dock where dozens of huge tarpon fish (some 5-6 feet long) are waiting. Hand-feeding these powerful tarpon is a thrill (watch your fingers and hold on tight to your fish the tarpon leap out of the water!). It’s a classic Keys experience and makes for great photos. After feeding the tarpon, you can browse the open-air market shops at Robbie’s and then grab a bite at the on-site Hungry Tarpon restaurant perhaps try a basket of conch fritters and definitely save room for a slice of key lime pie with a waterfront view. Islamorada is also a prime spot for sportfishing charters, but even a quick stop at Robbie’s gives you a taste of the Keys’ quirky, laid-back charm.

Back on the Overseas Highway, you’ll soon traverse the engineering marvel that is the Seven Mile Bridge, connecting the Middle Keys to the Lower Keys. This bridge offers jaw-dropping panoramic views turquoise Atlantic on one side, emerald Gulf on the other, and tiny islands dotting the expanse. There is a section of the old Seven Mile Bridge (built in the early 1900s) that is now a pedestrian/bike trail to Pigeon Key, a small historic island. It’s worth stopping at the Old Seven Mile Bridge access in Marathon if you want to stretch your legs you can walk a portion of the original bridge for bonus views and a sense of history. Even from the main bridge, you might spot wildlife; keep an eye out for pelicans, frigatebirds, or even the occasional sea turtle or dolphin in the waters below.

Finally, you’ll arrive in Key West, the southernmost city in the continental United States and truly a world of its own. Key West is a tropical, quirky town with conch-style architecture, swaying palms, roaming roosters, and a live-and-let-live ethos you’ll immediately see why so many say it “feels like a different world”. Start by exploring Old Town Key West. Duval Street is the main strip, running from the Gulf to the Atlantic, and it’s the heart of Key West’s anything-goes nightlife and daylife. By day you can shop art galleries and boutiques or visit cafes; by night, Duval comes alive with live music spilling out of bars (don’t miss a visit to Sloppy Joe’s Bar, a favorite hangout of Ernest Hemingway, or Hog’s Breath Saloon for live rock music). There’s a saying that “anything can happen on Duval Street,” and it’s often true the mix of locals, tourists, street performers, and party-goers makes it an unforgettable scene.

For history buffs and literary fans, tour the Ernest Hemingway Home & Museum, a beautiful Spanish Colonial house where Hemingway lived in the 1930s. The house and gardens are lovely and they’re inhabited by dozens of polydactyl cats (many with six toes), descended from Hemingway’s own pet cats. You’ll see these pampered felines lounging everywhere. A guided tour of the home offers insight into Hemingway’s life and the unique environment of Key West that inspired him. Another landmark is the Southernmost Point Buoy, a colorful concrete buoy marking the southern tip of Key West (only ~90 miles from Cuba!). It’s a fun photo-op symbolizing that you’ve reached the literal end of the road in the USA.

Every evening in Key West, there’s one event you must attend: the Sunset Celebration at Mallory Square. Head to the waterfront about an hour before sunset, where crowds gather to applaud the day’s end. Street performers, musicians, and food carts create a carnival-like atmosphere as the sun sinks toward the horizon. When the sun finally sets over the Gulf in a blaze of color, the whole square cheers it’s a beloved local tradition that captures Key West’s celebratory spirit. Afterward, you can continue the night with live music Key West has everything from reggae and trop-rock bands to jazz, not to mention famous drag shows and dive bars.

Key West’s tropical and eccentric charm will make you feel far removed from the mainland. The Conch Republic (as Key West whimsically calls itself) operates on “island time.” Days here are filled with visits to white-sand beaches (try Fort Zachary Taylor State Park for a mix of beach and history), snorkeling or kayaking tours, and perhaps a slice of key lime pie at the original Kermit’s Key Lime Shoppe. Nights are for embracing the lively spirit along Duval. As you soak in the warm tropical breeze and live music under glowing neon tavern signs, you’ll understand why so many visitors fall in love with Key West’s one-of-a-kind vibe it’s “a vibrant, quirky, and proudly eccentric town unlike any other in America,” as one observer aptly put it.

Road Trip Tips: The drive from Miami to Key West can be done in 4 hours non-stop, but plan for a full day with stops traffic on the two-lane Overseas Highway can get slow behind trucks or at drawbridges, and you’ll want to pause for photos. There are plenty of roadside parks and beaches (Anne’s Beach, Bahia Honda State Park, etc.) to enjoy along the Keys. Weekends can be crowded, so start early if you want to beat the rush to popular stops. In Key West, park the car and explore on foot or by bike the island is small (about 4 miles long) and very walkable, and parking can be limited in Old Town. Be sure to stay hydrated (tropical sun + margaritas can sneak up on you) and don’t forget sunscreen. If you have extra days, consider a snorkel trip to Dry Tortugas National Park (accessible by ferry or seaplane from Key West) or simply indulge in “island time” by lounging in a hammock. This road trip offers the ultimate Florida experience, from neon Miami to the mellow Florida Keys an adventure you’ll reminisce about at every sunset.