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Key West Road Trip

Drive the Overseas Highway

From Miami’s retro beachfront and sleek skyscrapers, drive south over the ocean to tropical outposts

This road trip blends scenic drives with downtime in tropical surroundings. The views you’ll get from the Overseas Highway are spectacular. And when you arrive in the Florida Keys, you can turn off the engine and tune into laid-back vibes and sultry sunsets.

Tour type Self-drive

Visiting Miami, Marathon or Islamorada, Key West, Key Largo

Ideal for
Exploring the Florida Keys in style.

Recommended itinerary

Miami

Welcome to Florida

Touch down in Miami, ready to take this incredible city head-on. Whether you’re after a shopping break, beach break, or cultural break, Miami delivers. Base yourself on the sands, near a mall, or on Ocean Drive near the beautiful Art Deco buildings. After your city break, pick up your hire car and drive south on the Overseas Highway.

What to do in Miami

Orientate yourself

Explore Miami's Art Deco buildings, modern skyscrapers, lush Coconut Grove, vibrant Coral Gables and Little Havana on a four-hour guided tour. Finish with sundowners over Biscayne Bay.

Where to stay in Miami

Choose your perfect city stay

Miami is home to a plethora of luxurious resorts. Whether you prefer the quieter end of Ocean Drive (check out The Betsy), prefer being in the centre of the action at the iconic Fontainebleau, or want to stay at one of the newer additions like 1 Hotel South Beach, there is a fantastic selection of resorts for you to choose from.

Islamorada or Marathon

A stop on the Way to Key West

We highly recommend stopping for a night or two on the way down to Key West to break up the journey but more importantly, to see more of the Keys. You could stop off on Islamorada, a diving and snorkelling hot spot, or Marathon, a great choice for families thanks to its sandy beaches and fun and friendly vibe.

Key West

Drive south

Allow a whole day for your drive south from Miami to Key West. Crossing the Overseas Highway that links the Florida Keys is an incredible journey. Plan for plenty of stops along the way to admire the view.

What to do in Key West

Take the trolley

See Key West’s first tourist attraction, the Key West Aquarium, the world’s first open-air aquarium, then find yourself back in the 1800s at the Key West Shipwreck Treasure Museum. Stop by the Ernest Hemingway House Museum and marvel at the beautiful species of butterflies in the Key West Butterfly and Nature Conservatory.

Where to stay in Key West

Tranquil and tropical

Choose a resort on a natural sand beach, or opt for a hotel that’s right by Mallory Square and enjoy the buzz of this eclectic neighbourhood.\n

Key Largo

Back on the Overseas Highway…

Having reached the southernmost point of the USA at Key West, you’ll retrace your journey across the Keys on a hundred-mile drive to Key Largo. It’s said to be the Dive Capital of the World, but even if you’re not a certified diver, you can enjoy excellent snorkelling here or even a glass-bottom boat trip to stay dry.

What to do in Key Largo

Relax or roam?

Spend your final few days relaxing, or perhaps you’ll want to get out on the water and board the historic steamboat, The African Queen, to cruise the canals of Key Largo. You’re also within easy distance of the Everglades from Key Largo.

Where to stay in Key Largo

Check into Baker’s Cay

We love the tranquil Baker’s Cay Resort on a small private beach. Other facilities to keep guests busy include two outdoor pools with waterfall grottoes, a pool bar, two tennis courts, and a spa. Nearby, John Pennekamp Coral Reef State Park tempts snorkellers and divers to its coral reef.\n\n

Set sail

Add a cruise to your holiday

Miami is the largest and busiest cruise ports in the USA, with ships leaving for the islands of the Caribbean, the shores of South America and beyond. It's easy to add a voyage to the end of your self-drive; a couple of our cruise partners that feature round-trips from here (or 30 miles up the I-95 in Fort Lauderdale) include luxe line Celebrity Cruises, and Royal Caribbean International with its facility packed ships that are a real favourite with families.

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