Drive 113 miles of the Overseas Highway from Miami to Key West, island-hopping through Key Largo, Islamorada, Marathon, and Big Pine Key. A complete 7-day Florida Keys itinerary with practical advice.
Few drives feel quite like the Overseas Highway. For about 113 miles, US-1 hops from island to island across 42 bridges, with shallow turquoise water on both sides and green mile markers counting down to zero. It is the road that replaced Henry Flagler's Overseas Railroad, wrecked by the 1935 Labor Day Hurricane, and it ends at Mile Marker 0 in Key West, the southernmost city in the continental United States.
This Florida Keys road trip itinerary runs north to south from Miami to Key West over six nights. The driving is easy: no single leg takes much more than an hour, which leaves the days free for reefs, beaches, and key lime pie. Below is the route, stop by stop, with the timing and practical detail you need to plan it.
The Keys reward a slow pace. You could drive Miami to Key West in three and a half hours without stopping, but that misses the point. Base yourself in three towns — Key Largo, Marathon, and Key West — rather than changing hotels every night, and use day trips to reach the islands in between. Come in the dry winter season, roughly November to April, to dodge the summer heat and the June to November hurricane season.
Most trips begin in Miami, usually with a rental car picked up at the airport. Give the city a morning before heading south: the Art Deco waterfront of South Beach, the murals of Wynwood, and Cuban coffee and food in Little Havana are all worth your time. This is also the place to stock up, as groceries, snorkel gear, and reef-safe sunscreen all cost more once you are on the islands. Leave mid-morning to clear the city traffic, fill the tank before Key Largo, and turn south onto US-1.
An easy 90-minute drive brings you to Key Largo, the first and largest of the Keys, which calls itself the dive capital of the world. The headline attraction is John Pennekamp Coral Reef State Park, which protects part of the only living coral barrier reef in the continental US. Snorkel boats, dive trips, and glass-bottom tours all run out to the reef and the famous submerged Christ of the Abyss statue. Book a day ahead and take a morning departure for the calmest water. Topside, paddle a kayak through the mangrove creeks or visit the History of Diving Museum.
On your second day, take the short drive south to Islamorada, a chain of small islands that markets itself as the sportfishing capital of the world. Even if you never pick up a rod, the appeal is clear: Robbie's Marina, where you can feed the enormous tarpon off the dock; Anne's Beach, with its warm shallow water and boardwalk; and a row of bayside restaurants that serve up the best sunsets on the drive. Arrive early at a waterfront table for the evening, and if you want to fish, book a charter in advance. Two nights in Key Largo gives time for the water and an easy day trip before you push on.
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Marathon, in the Middle Keys, is the gateway to the Seven Mile Bridge and a good base for two nights. The Seven Mile Bridge is the drama of the drive down from Key Largo: the modern bridge carries the highway over open water, while a long section of the old railroad bridge runs alongside it as a walking and cycling path toward Pigeon Key, the island that housed the railroad's construction camp.
In town, the Turtle Hospital runs 90-minute guided tours of its rescue and rehabilitation work, and these book out fast in winter, so reserve ahead. Sombrero Beach is the best swimming beach in town, and Crane Point Hammock has shady tropical forest trails and a small nature centre.
Give your second day to Big Pine Key, a short drive south and the quiet heart of the Lower Keys. It is the home of the Key deer, a tiny endangered subspecies found nowhere else, protected within the National Key Deer Refuge. Dawn and dusk are the times to spot them, and you will see signs urging drivers to slow down because deer cross the road. Neighbouring Bahia Honda State Park is the reason many people rate this the prettiest stop of all. Calusa Beach has pale sand and clear shallow water, and you can climb a surviving section of the old Bahia Honda railway bridge for a view across the islands. Cap the evening at the No Name Pub, a backwoods bar whose walls are papered with signed dollar bills.
The highway ends at Mile Marker 0 in Key West, and after the short drive down from Marathon the car can finally rest. Old Town is compact and walkable, so park up and explore on foot or by bike. The Ernest Hemingway Home and Museum, where the writer lived in the 1930s, still keeps the descendants of his six-toed cats. Fort Zachary Taylor has the best swimming beach in town and shady picnic grounds.
No evening here is complete without the Sunset Celebration at Mallory Square, a nightly gathering of street performers and food carts where the crowd applauds the sun into the Gulf of Mexico. With two nights you also have time for the standout day trip: Dry Tortugas National Park, 70 miles west, where the huge brick fortress of Fort Jefferson sits on a remote island ringed by coral. It is reachable only by ferry or seaplane, and the ferry seats sell out well ahead in winter. Your final morning is for a last swim or a slow breakfast before the drive back north.
The dry season, November to April, is the time to come. The weather is warm but not oppressive, humidity is lower, and you avoid the heart of the Atlantic hurricane season, which runs June to November. December through April is peak season, so book accommodation and key activities such as Dry Tortugas tours and the Turtle Hospital well in advance. Summer is hot, humid, and prone to afternoon storms, though the water is at its warmest.
Navigation: Addresses in the Keys are given by mile marker (MM), counting down from Homestead to MM0 in Key West. It is the easiest way to find anything.
Fuel: Top up in Miami, Key Largo, Marathon, and Big Pine Key. Fuel is more expensive the further south you go.
Driving: Much of US-1 is a single lane in each direction. Be patient, do not tailgate, and use the marked passing zones rather than risking the oncoming lane.
Wildlife: Slow down on Big Pine Key, especially after dark, where Key deer crossings are frequent and fines for speeding are high.
Booking ahead: Reef trips, fishing charters, the Turtle Hospital, and the Dry Tortugas ferry all sell out in winter. Reserve before you arrive.
Hurricane season: If you travel between June and November, watch the forecast and have a flexible plan, as storms can close the highway.
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The full route — stops, maps, and driving times — is on Routebook by Kington.
A 7-day drive down the Overseas Highway from Miami to Key West, island-hopping through Key Largo, Islamorada, Marathon, and Big Pine Key, with reef snorkelling, the Seven Mile Bridge, and Mile Marker 0.
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