Drive Florida’s Overseas Highway:
A Sun-Soaked Road Trip to the Edge of America
...113 miles of turquiose views, epic eats and island vibes
Drive the Overseas Highway:
113 miles of turquoise views, epic eats, and island vibes.
If roads could flirt, the Overseas Highway would wink at you from across the bar. This 113-mile stretch from mainland Florida to Key West is part road, part engineering marvel, part tropical daydream—and it’s been making travelers swoon since the 1930s.
A Little Backstory Before the Breeze Gets in Your Hair
The highway follows the path of Henry Flagler’s ambitious Florida East Coast Railway. Flagler, a railroad tycoon with pockets as deep as his ambition, decided in the early 1900s to connect the Keys to the mainland by train. It was a feat of vision (and stubbornness), completed in 1912… only for much of it to be destroyed by the catastrophic Labor Day Hurricane of 1935. Rather than admit defeat, the state of Florida repurposed surviving railway bridges for cars, opening the Overseas Highway in 1938. Over time, modern replacements have taken over, but you can still spot sections of the old railroad bridges standing proudly beside the roadway—a weathered reminder of the Keys’ grit.
Where the Road Begins: Key Largo
Leaving the mainland, you’ll pass through the Everglades’ watery fringes before arriving in Key Largo, the “Diving Capital of the World.” If you’re a snorkel or scuba fan, John Pennekamp Coral Reef State Park is a must. This was the first US undersea park, a swath of 25 miles established to protect the only living coral reef in the continental US. Even if you stay dry, a glass-bottom boat tour lets you spy on parrotfish, coral, and maybe a curious sea turtle.
Before you get too far, stop for Key lime pie on a stick (yes, you read that correctly!) at Key Largo Chocolates, enjoy the conch fritters at Alabama Jacks, grab a slice at Upper Crust Pizza—a Key Largo staple—or stock up on road snacks from the local Publix. (Trust me, their fried chicken becomes legendary when paired with ocean views later at Sombrero Beach.)
At mile 92 is the Key Lime Pie Factory. Yes, you need to stop and indulge.
You won’t be able to miss the giant lobster at mile market 86.7, at the Rain Barrel Village. This is a slightly kitchy tropical oasis filled with shops. If you’re looking for some souvenirs, this may be your stop.
Midway Magic: Islamorada
Next up is Islamorada, known for sport fishing and sunsets that deserve a slow clap. Stop at Robbie’s Marina to hand-feed massive tarpon (and dodge the pelicans, who have zero respect for personal space). If you’re a beer enthusiast, pop into Florida Keys Brewing Company (mile marker 81.6 in the Morada Way Arts & Cultural District) for a cold pint in a colorful, mural-covered beer garden. You can even make some new friends here over a game of giant Jenga or cornhole.
Feeling beachy? Pull over at Anne’s Beach, where shallow turquoise water stretches far out—perfect for wading, picnicking, or just watching kite surfers zip by. Mile marker 73.5.
Seven Mile Wonder & Sombrero Bliss
Driving over the Seven Mile Bridge feels like flying low over the water. Keep your eyes peeled for Old Seven, the retired section of bridge now open to pedestrians and cyclists. Just past Marathon, turn off for Sombrero Beach—the spot for that Publix chicken picnic you packed earlier. To balance it out, consider a visit to the Turtle Hospital, where rescued sea turtles get a second chance at life.
Bahia Honda & Big Pine
Bahia Honda State Park (mile marker 36.8) serves up some of the clearest water in the Keys and sweeping views from the old bridge. Just down the road, you’ll find the Blue Hole on Big Pine Key, a freshwater quarry where you might spot Key deer or even an alligator.
Rolling Into Key West
Welcome to the southernmost point in the continental U.S.—where roosters roam free and pastel houses keep watch under swaying palms. Start your day at La Grignote or Moondog Café for a breakfast worth lingering over. Take a key lime pie tasting tour with Tart Tales, or hop on a kayak trip to the Key West sandbars for shallow-water bliss. This is a magical experience on turquoise waters.
For live music, grab a seat at the Green Parrot Bar, a legendary watering hole with no dress code other than “be yourself.” Beer lovers can toast their arrival at the Southernmost Pint Brewpub. The No Name Pub is another staple of the Florida Keys. Casual, and with some great food and cold drinks.
For a splurge, book Latitudes on Sunset Key—just make your reservation far in advance. And when you need a place to call it a night, the Orchid Key Inn offers boutique comfort with a pool you’ll actually want to use.
Bonus Adventures: Stock Island & Beyond
Just across the bridge from Key West, Stock Island is worth a detour. Start at Hurricane Hole Marina for a mangrove kayak tour with Lazy Dog, then stroll to Croissants de France for buttery perfection. Visit the Key West First Legal Rum Distillery, where barrels are soaked in salt water for a uniquely coastal flavor, then finish with dinner at Onlywood, a charming Italian spot just off Duval Street.
If time allows, catch the ferry to Dry Tortugas National Park—a historic fort ringed by turquoise water that feels like your own private Caribbean outpost.
Tips for the Trip
- Take it slow: This is a “linger” road trip, not a “make good time” road trip.
- Pack snacks (and patience): Traffic can be part of the Keys experience, but the views make up for it. Stop off and walk about whenever you need to. Oh, and a stop at the Robert is Here Fruit Stand is a must.
- Sunscreen is non-negotiable: There’s a lovely ocean breeze that tricks you into thinking you’re not getting burned.
- Expect showers in the afternoon and Hurricanes in early Autumn: Tropical showers are common, especially in the summer. August/September/October are prime hurricane season months. If you are visiting then, DO NOT ignore mandatory evacuations if a big storm is rolling through.
The Overseas Highway is a sun-drenched, key lime-scented rite of passage if you love a good road trip. With salty breezes in your hair and one of America’s most scenic roads unfurling in front of you, you might just find yourself wishing it never ended.
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Happy Travels!
