Miami to Key West Road Trip: 5 Days Down the Florida Keys
The Overseas Highway, island by island.
A 5-day Miami to Key West road trip down the Overseas Highway — island stops, water views and easy beach days, planned day by day in both directions.
South Beach
Iconic Art Deco district and beach perfect for morning photos before hitting the road.
Versailles Restaurant Cuban Cuisine
Legendary Cuban food spot in Miami, a local institution worth a stop before departure.
John Pennekamp Coral Reef State Park
First underwater park in the US, offering glass-bottom boat tours and snorkeling over vibrant reefs.
Alabama Jacks
Quirky waterfront seafood shack with conch fritters and Keys character, a classic Overseas Highway stop.
Seven Mile Bridge
One of the most photographed bridges in the world, spanning turquoise waters between the Keys.
Bahia Honda State Park
Home to some of the best beaches in the Keys with calm, clear water ideal for swimming and photos.
Keys Fisheries
Waterfront spot in Marathon famous for its lobster reuben and fresh stone crab.
Mallory Square
Famous for its nightly sunset celebration with street performers and unbeatable water views.
Duval Street
The heart of Key West's colorful, lively culture, lined with historic architecture and local shops.
Blue Heaven
Bohemian courtyard restaurant famous for its Key West shrimp and laid-back island vibe.
Fort Zachary Taylor Historic State Park Beach
Best beach in Key West for swimming and sunset photos, tucked beside a historic fort.
Key West Key Lime Pie Co.
A must-try tasting of the town's signature dessert.
Turtle Hospital
Rescue center offering an intimate, meaningful look at sea turtle conservation in the Keys.
Anne's Beach
Quiet, scenic shallow-water beach great for a relaxed afternoon and photos.
Lazy Days Restaurant
Beachfront dining in Islamorada known for fresh local seafood and sunset views.
Overnight in Islamorada
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Islamorada · $$
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Joe's Stone Crab
Miami's most iconic seafood institution, the perfect final meal to close out the trip.
Wynwood Walls
Vibrant outdoor street art museum offering a colorful, photogenic farewell to Miami.
Make this trip your own
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