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 9-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 nine 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 two or three towns rather than changing hotels every night, and use day trips to reach the rest. Come in the dry winter season, roughly November to April, to dodge the summer heat and the June to November hurricane season.
Miami is where most trips begin, usually with a rental car picked up at the airport. Give it a day 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, and fill the tank before Key Largo.
Key Largo is the first and largest of the Keys, and it 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. Two nights here gives time for the water and a slow start before you push on.
A short half-hour south, Islamorada is 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.
Seven nights from Kotor through the Adriatic Riviera, down to Ulcinj, across Lake Skadar and back over Lovćen mountain. A practical itinerary for Montenegro's Sea and Heights loop.
It makes an easy one-night stop. Arrive early at a waterfront table for the evening, and if you want to fish, book a charter in advance.
Marathon, in the Middle Keys, is the gateway to the Seven Mile Bridge and a good base for two nights. 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.
The Seven Mile Bridge itself is the drama of this stretch. 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.
Just over the bridge, Big Pine Key is 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 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.
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.
White chalk cliffs, a Norman conquest battlefield, cobblestoned medieval streets and a seaside city that refuses to be ordinary: this East Sussex road trip itinerary covers it all in seven days.
The full route — stops, maps, and driving times — is on Routebook by Kington.
A 9-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.
Routebookby Routebook
