Florida Keys: 180 km of road above the ocean, all the way to Key West

The Keys are a string of islands stretching about 180 km south of Miami. A single road links them, the Overseas Highway, which hops from island to island over 42 bridges all the way to Key West. For long stretches you drive with the sea on both sides. Here, the journey matters as much as the destination.

History and origins

The history of the Keys is bound up with Henry Flagler, who had made his fortune with Standard Oil before going into railways. Between 1905 and 1912 he had a railway built over the sea, from Miami to Key West. At the time the project was thought mad. Yet the first train reached Key West in January 1912.

On 2 September 1935, a Category 5 hurricane, the most powerful ever to hit the United States, destroyed a large part of the line. It killed at least 485 people, including about 260 First World War veterans employed on a road-building project in the islands.

The railway was not rebuilt. The State of Florida bought what was left and turned it into a road: the Overseas Highway opened in 1938, reusing some of the railway bridges. It was designated an “All-American Road” in 2009, the highest distinction for a scenic road in the United States.

Key West, the last island, has always been a place apart. It was a prosperous fishing and trading port as early as the 19th century. In the 20th it drew artists and writers, among them Ernest Hemingway, who lived there from 1931 to 1939.

What to do there

• John Pennekamp Coral Reef State Park 📷Two palm trees beside the lagoon at John Pennekamp park: in Key Largo, the first underwater park in the United States. Boats take you out to snorkel or dive on the reef, notably around a submerged statue of Christ.
• Islamorada: the capital of sport fishing, with plenty of trips out to sea.
• Sombrero Beach 📷The palm trees of Sombrero Beach at sunset: Marathon’s beach, lined with palm trees. Access is free, but the car park right in front charges: $5 an hour for the first two hours, then $2 an hour.
• The Seven Mile Bridge: the best-known bridge on the route, nearly 11 km above the sea on the way out of Marathon. Alongside it, a section of the old bridge reopened in 2022 to walkers and cyclists, for 3.5 km as far as the islet of Pigeon Key.
• Bahia Honda State Park 📷A beach with clear, shallow water at Bahia Honda: sandy beaches on both sides of the island, which is rare in the Keys, and an old bridge from Flagler’s railway that stops dead above the water.
• Duval Street 📷The lit-up bars of Duval Street, in Key West: the main street of Key West, with its bars, galleries and shops. The streets around it are lined with white or pastel wooden houses 📷Colourful conch-style houses in Key West.
• Sunset 📷Sailing boats in silhouette after sunset in Key West: in Key West it’s a daily ritual. The best known is at Mallory Square, with its street performers. Higgs Beach is quieter.
• Fort Zachary Taylor 📷Fort Zachary Taylor seen from the ramparts: a 19th-century brick fort at the tip of the island, and right next to it one of the best beaches in Key West for snorkelling 📷The beach at Fort Zachary Taylor and its turquoise water.
• The Ernest Hemingway Home 📷The entrance to Ernest Hemingway's house in Key West: his house is now a museum, also known for its dozens of six-toed cats, descendants of the writer’s own.
• The Southernmost Point: the big buoy marking the southernmost point of the continental United States.

Stories and good to know

• Despite its name, the Seven Mile Bridge is not seven miles long but 6.79, or 10.9 km.
• Addresses are given in “mile markers”, small green signs at the roadside. They count the miles to Key West, where mile 0 is.
• The Keys are fringed by the only living coral barrier reef in the continental United States, the third largest in the world.
• Key West is closer to Havana than to Miami: about 170 km one way, 240 the other. You can feel it, too, in a culture and atmosphere that are more Latin than American.
• In Key West, hens and roosters roam free all over town 📷A rooster and a hen roaming free in Key West, protected by the city. Don’t count on a lie-in.
• The local speciality is key lime pie, made with the small limes of the Keys.

Practical information for your road trip

• On the road: there is only one lane in each direction for much of the way. At the slightest accident the tailbacks stretch for kilometres, with no possible detour. Leave early.
• In Key West: the town is small and flat, so you leave the car at the hotel. Hotel guests also get around by golf cart.
• State parks: they are not covered by the national parks pass.
• Hemingway Home: $19 per adult.
• Budget: staying in the Keys, especially in Key West, costs considerably more than elsewhere in Florida.
• Combine it with: the Keys follow on naturally from Miami and the Everglades. That’s what we did on our road trip 2 (see below).

Our experience in the Keys

We spent three nights there in early January 2026, two in Key West and one in Key Largo:

⏳ Our day-by-day journals are coming soon.