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Key West Road Trip
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.
Ideal for
Exploring the Florida Keys in style.
Itinerary overview
Days 1 to 3: Miami
Welcome to Florida
Touch down in Miami, ready to take this incredible city head-on. Whether you’re after a shopping ...
Day 4: 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 journ...
Days 5 to 6: Key West
Drive south
Allow a whole day for your drive south from Miami to Key West. Crossing the Overseas Highway that...
Days 7 to 8: Key Largo
Back on the Overseas Highway…
Having reached the southernmost point of the USA at Key West, you’ll retrace your journey across ...
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 t...
Days 1 to 3: 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. 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.
Day 4: 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.
Days 5 to 6: 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. 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.
Days 7 to 8: 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. 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.
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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