Florida Keys Road Trip Itinerary: Miami to Key West
By Jeff Lowe • August 19, 2025
If you have ever dreamed about cruising down an endless highway with turquoise water on both sides, the Florida Keys road trip is calling your name. Honestly, it is one of the most fun and laid-back drives in the U.S. The trip stretches about 113 miles from Miami to Key West along the famous Overseas Highway, hopping across a chain of tropical islands that feel like the Caribbean without needing a passport.
So, grab your sunglasses, crank up some beachy tunes, and let’s talk about the ideal route down the Keys.
Start in Miami (or Key Largo if you’re short on time)
Most people kick things off in Miami, and it’s a great spot to fuel up on Cuban coffee and pack some snacks before hitting the road. If you’re tight on time, you can skip Miami and start right in Key Largo, the first of the Keys. But if you can swing it, the drive out of Miami really sets the stage—you’ll feel the city fading as palm trees take over.
Key Largo
Your first stop, Key Largo, is only about an hour from Miami. It’s a paradise for divers and snorkelers. If you’re into exploring underwater, the John Pennekamp Coral Reef State Park is worth the stop for its colorful coral and tropical fish.
If you’d rather stay dry, hop on a glass-bottom boat tour or just kick back with a fresh seafood lunch. This is also a good spot to try Key lime pie for the first time, though you’ll probably have it again and again before the trip is over.
Islamorada
Next up is Islamorada, known locally as the sportfishing capital of the world. Even if you’re not into fishing, the island has a breezy, small-town feel. Stop for a drink at a tiki bar, wander around the local shops, or just stretch your legs by the water.
If you have time, check out some of the art galleries here. It has a surprisingly creative scene. And don’t miss the evening sky here, which tends to put on quite a show.
Marathon
Keep cruising south and you’ll hit Marathon, about halfway to Key West. This is where things get really fun because you’ll cross the famous Seven Mile Bridge. It is exactly what it sounds like: a bridge that stretches across open water for miles, and driving it feels surreal.
Marathon itself is worth a stop too. If you love animals, swing by the Turtle Hospital, where they rescue and rehabilitate sea turtles. It’s a heartwarming and interesting place to visit.
Big Pine Key
After Marathon, the pace slows down even more. Big Pine Key is home to the tiny Key deer, which are miniature white-tailed deer that roam around freely. Keep an eye out for them, especially as the sun starts to go down.
You will also find quieter beaches here if you are looking to escape the crowds for a bit. It is a peaceful place to reset before the final stretch to Key West.
Key West
Finally, you roll into Key West, the southernmost point of the continental U.S. The island mixes quirky charm, history, and a heavy dose of island time.
Stroll down Duval Street for bars, live music, and people-watching. Visit Ernest Hemingway’s old house, where the famous polydactyl cats still lounge around. And definitely make time for Mallory Square in the evening, which turns into a nightly gathering with street performers, musicians, and ocean views.
Oh, and yes—more Key lime pie. You can never have too much.
Tips for the Drive
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Take it slow. The whole drive can be done in about four hours, but the fun is in stopping along the way. Spread it out over three or four days if you can.
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Stay overnight. Places like Key Largo, Islamorada, or Marathon make great overnight stops so you aren't rushing.
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Bring snorkel gear. The Keys are all about the water, and you’ll want to jump in at least once or twice.
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Plan for sunsets. Each island has its own unique vantage point, so don’t just save your sunset watching for Key West.
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Pack light and comfy. Flip-flops, swimsuits, and casual clothes are the unofficial uniform here.
See You Down the Overseas Highway
Driving the Florida Keys gives you the rare combination of a breezy island vacation and the freedom of the open road. It’s a route defined by sudden ocean views, roadside shacks, and plenty of excuses to pull over just to take it all in.
Roll the windows down, let the salt air in, and enjoy the ride.