Florida Keys Road Trip Itinerary: Miami to Key West

If you’ve ever dreamed about cruising down an endless highway surrounded by turquoise water on both sides, then the Florida Keys road trip is calling your name. Honestly, it’s 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 sunnies, crank up some beachy tunes, and let’s talk about the perfect Florida Keys road trip itinerary.

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 – “Diving Capital of the World”

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 a must. They say it’s “like visiting an underwater park,” with colorful coral and tropical fish everywhere.

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 (spoiler: you’ll probably have it again… and again).

Islamorada – Sportfishing and Sunset Vibes

Next up is Islamorada, known as the Sportfishing Capital of the World. Even if you’re not into fishing, the island has that breezy, small-town Keys feel. Stop for a drink at a tiki bar, wander around the cute local shops, or just stretch your legs by the water.

If you have time, check out some of the art galleries here—it’s got a surprisingly creative vibe. And don’t miss the sunset. Islamorada has some of the most colorful skies you’ll ever see.

Marathon – Seven Mile Bridge & Turtle Hospital

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’s exactly what it sounds like: a bridge that feels like it stretches forever across open water. Driving it is pure magic.

Marathon itself is worth a stop too. If you love animals, swing by the Turtle Hospital where they rescue and rehab sea turtles. It’s heartwarming and super educational.

Big Pine Key – Home of the Tiny Deer

After Marathon, the vibe gets even more relaxed. Big Pine Key is home to the adorable Key deer, which are basically miniature white-tailed deer that roam around freely. Keep an eye out because they’re everywhere, especially at dusk.

There are also some quieter beaches here if you’re looking to escape the crowds for a bit. It’s a great place to reset before the final stretch to Key West.

Key West – The Grand Finale

Finally, you roll into Key West, the southernmost point of the continental U.S. And wow, it’s the perfect finale to the road trip. The island is a mix of quirky charm, history, and tropical vibes.

Stroll down Duval Street for bars, live music, and people-watching. Visit Ernest Hemingway’s old house (yes, the cats are still there). And definitely make time for Mallory Square at sunset. It turns into a nightly festival with street performers, musicians, and one of the best sunsets you’ll ever see.

Oh, and yes—more Key lime pie. You can never have too much.

Tips for the Perfect Florida Keys Road Trip

Take it slow. The whole drive could technically be done in about 4 hours, but the fun is in stopping along the way. Spread it out over 3-4 days if you can.
Stay overnight. Places like Key Largo, Islamorada, or Marathon make great overnight stops so you’re not rushing.
Bring snorkel gear. The Keys are all about the water, and you’ll want to jump in at least once or twice.
Plan for sunsets. Each island has its own unique sunset vibe—don’t just save it for Key West.
Pack light but comfy. Flip-flops, swimsuits, and casual clothes are the dress code here.

Wrapping It Up

A Florida Keys road trip is one of those bucket-list adventures that’s both relaxing and exciting at the same time. You’ve got the freedom of the open road, island-hopping fun, and plenty of “pull over and take a picture” moments.

From snorkeling in Key Largo to sipping cocktails in Key West, this trip has a little bit of everything. So, if you’ve been craving sunshine, turquoise water, and a road trip that feels like a vacation in itself, the Florida Keys is waiting for you.

Hop in the car, roll down the windows, and get ready for one unforgettable ride.