About This Trip
The Overseas Highway — US Route 1 through the Florida Keys — is unlike any other road in America. For 113 miles of its length, the highway is elevated over open water, crossing 42 islands and the gaps between them on a series of bridges that together stretch over 17 miles. Driving it feels less like a road trip and more like a boat trip that happens to use a car.
The drive begins in earnest at Homestead, just south of Miami, where the suburban sprawl gives way abruptly to the flat limestone plain of the upper keys. Key Largo is the first island — and the largest — famous for its diving, particularly John Pennekamp Coral Reef State Park, the first undersea park in the continental United States. The water here shifts through every shade of blue and green depending on depth and time of day.
Islamorada calls itself the Sport Fishing Capital of the World, and the claim is defensible. Tarpon, bonefish, and permit are chased year-round in the shallow flats. Even if you don't fish, the sunsets here are famous, and the restaurants — particularly the raw bars and fish houses — are excellent.
The Seven Mile Bridge, connecting Marathon to the Lower Keys, is the defining image of the Overseas Highway. Seven miles of elevated roadway with nothing visible on either side but open water. The original Flagler Railroad bridge runs parallel, now converted to a pedestrian and cycling path. On a clear day, looking back at the old bridge from the new one, the visual effect is borderline surreal.
Key West is the end of the road — literally. The southernmost point in the continental United States sits here, 90 miles from Cuba. The town's compact, walkable historic district is full of Victorian architecture, open-air bars, and the particular energy of a place that has always attracted people who decided to drive until they ran out of land.
Best time to drive: November through April. Summer brings heat, humidity, and hurricane season. Winter weekends in Key West are busy; plan to arrive mid-week if possible. The drive from Miami to Key West takes three to four hours without stops — allow a full day for the full experience.
Stops
Homestead, FL — Gateway to the Keys
The last mainland stop before the islands begin. Fill your tank here — fuel in the Keys is significantly more expensive. The Everglades are a short detour west if you have time. From Homestead, the highway crosses Card Sound or the wider and more dramatic Route 1 causeway into Key Largo.
Key Largo
The largest Key and the one that sets the tone for everything that follows. John Pennekamp Coral Reef State Park offers snorkeling and glass-bottom boat tours over living reef. The African Queen — Humphrey Bogart's actual movie boat — is docked at the Holiday Inn marina and still runs canal tours.
Islamorada
A string of five islands with serious fishing culture and excellent waterfront restaurants. Robbie's Marina is famous for its enormous tarpon that you can hand-feed from the dock — a chaotic and completely worthwhile experience. Sunrise and sunset here, with nothing blocking the horizon on either side, are exceptional.
Marathon — Seven Mile Bridge
Marathon is the midpoint of the Keys and the launch point for the Seven Mile Bridge — the single most iconic section of the Overseas Highway. Stop at the Pigeon Key parking area at the Marathon end for the best view of both bridges running parallel over open water. The Turtle Hospital on Marathon is open for daily tours.
Key West
The end of the road. Walk Duval Street, touch the Southernmost Point buoy, and eat stone crab at any of a dozen excellent waterfront restaurants. Ernest Hemingway's house is a museum and is still occupied by some 40-plus six-toed cats, descendants of his original animals. The sunset celebration at Mallory Square happens every evening and draws an extraordinary cast of street performers.