A Road Tripper’s Guide To The Florida Keys

For those of you who are considering taking a road trip down the Florida Keys, we highly recommend it. From the iconic city of Miami, you can jet across the islands in just under four hours if you want to cruise straight here to Key West. If you’ve got some extra time, there are plenty of beautiful islands and sights to see along the way.


Beginning in Miami is such a great way to start off a Florida Keys road trip. Explore vibrant South Beach (for lazing on the sand), the booming Downtown and Brickell areas (for some of the hottest new restaurants and bars), Little Havana (a classic for a taste of Cuba), and the amazing arts districts, Wynwood & the Design District (for strolling through galleries, trendy restaurants, and shops). From acclaimed food to world-famous nightlife, Miami has all you need to set a trip off right.

Southern Glades

After enjoying the Miami’s neon lights, head out of the city on Highway 1 South. Immerse yourself in local nature at the Southern Glades, which is a wildlife conservation land consisting of tree islands, marsh, and marl prairie. This is home to the last remaining populations of the Cape Sable seaside sparrow, a gorgeous animal worth seeing.

Key Largo

Moving further south on the Florida Keys road trip, you’ll hit Key Largo, one of the most famous islands in the Keys. You can hang out here and lay out on a gorgeous beach, go snorkeling over the John Pennekamp Coral Reef and have a night out eating and dancing. And if you start to get hungry, don’t miss Mrs. Mac’s Kitchen, a regional favorite for decades that serves some of teh best breakfast sandwiches in Florida. (Discover more of our favorite restaurants for a Key West Road Trip here!)


The next stop down is Tavernier, the largest island in the upper Florida Keys. Stop here for a true taste of the Keys at Blond Giraffe Key Lime Pie Factory. We’ll give you one guess as to which dessert we highly recommend here.


Scuba divers should definitely consider stopping off a little further south at Islamorada, a village famous for its vibrant coral reefs. Also here: historical diving museum, and a botanical state park with its own tropical forest. And if you time it for lunch, a stop at Loreilei’s is in order. The over-water spot serves seasonal seafood dishes and all-year favorites like Key conch chowder.

Duck Key

As you head further south, you’ll hit Duck Key — a small and gorgeous island. This is another stretch of the road trip that gives drivers and travelers an up-close look at the sunny life that exists here in the Florida Keys. With a population just under 500, it’s small-town vibes at their best.


Marathon is a city in the Florida Keys that is set on thirteen islands famous for world-class beaches and a magnificent barrier reef. There’s so much to see across Marathon including loggerhead turtles, beach state parks, lagoons, and tropical forests.

Big Pine Key

Big Pine Key is yet another place where you can stop off on your leisurely Florida Keys road trip down from Miami to Key West. It’s home to white sandy beaches and crystal clear water. You can stop here for snorkeling, eating — we love the tiny Triano’s Tacos, just off Highway 1 — or just relaxing.

Key West

All Florida Keys road trips lead to Key West. Home to the southernmost point in the United States, it stands out with a unique brand of conch culture that includes great seafood, sunset traditions, live music, and parties throughout the year.

For those of you looking for the best place to stay in Key West, Parrot Key Hotel & Villas was named one of the best new hotels in the world by Travel & Leisure in 2019. You can check out our resort accommodations here. For some more examples of what makes Key West a special destination, check out the Parrot Press.

Discover more of Key West

Planning a Key West getaway? Check out our hotel here, and book your Key West island paradise.

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