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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
Miami
Welcome to Florida
Touch down in Miami, ready to take this incredible city head-on. Whether you’re after a shopping ...
What to do in Miami
Orientate yourself
Explore Miami's Art Deco buildings, modern skyscrapers, lush Coconut Grove, vibrant Coral Gables ...
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 Dri...
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...
Key West
Drive south
Allow a whole day for your drive south from Miami to Key West. Crossing the Overseas Highway that...
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 aquari...
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 en...
Key Largo
Back on the Overseas Highway…
Having reached the southernmost point of the USA at Key West, you’ll retrace your journey across ...
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 ...
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...
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...
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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