Long Weekend
3 days · ~210 miles · from Miami
US 1 to the end of the road: forty-two bridges over turquoise water to Key West, with a hurricane monument, a rescued movie boat, tiny key deer and the last mile marker in America. The interstate ends where the fun starts.
This trip chains: The Overseas Highway
Starting in Miami, this 3-day itinerary connects The Overseas Highway. It suits travellers interested in parks, coast, mountains & water; barbecue, boudin, oysters & tamales; battlefields, the movement & the past. The day-by-day bases let you split roughly 210 miles into a sequence of visits rather than trying to cover every linked route end to end. Use the daily highlights to decide which places deserve your longest stops.
Budget an average of about 70 miles per day across the whole trip, or roughly 1.6–2.3 hours behind the wheel at an assumed 30–45 mph back-roads pace. This is a planning estimate, not a measured time for each leg: transfer days can be longer and rest days shorter. Add meal stops, tours, ferries, traffic and hikes separately; use each day's navigation link for current driving estimates.
Use these day-end areas to plan lodging; the map pins are orientation points, not hotel recommendations. The final day can be your departure day.
Choose your dates around the experiences below rather than assuming one season fits the entire trip. These notes come from the linked route guides; check current forecasts and official schedules.
Card Sound Road for a beer at Alabama Jack's, the African Queen still afloat in Key Largo, snorkel the reef at Pennekamp, then the 1935 Hurricane Monument at Islamorada — dinner and a sunset dock at the fishing capital. Make the reef outing the day's anchor and reserve it before filling the morning with roadside stops. Wind and sea conditions can change a boat plan; keep a land-based Key Largo visit as the alternative. The driver should skip the beer. Islamorada is the first-night base, giving the Middle Keys their own day rather than trying to reach Key West in one run.
An open-air conch shack on the old smugglers' road, serving conch fritters to bikers and boaters since the 1950s. The correct way to enter the Keys.
The actual 1912 steam launch from the Bogart-Hepburn film, rescued and running canal cruises. Bogie never came to Key Largo for the movie; the boat did, eventually.
A WPA crypt holding victims of the Labor Day storm, the most intense US landfall on record. It killed hundreds of WWI veteran bonus-army workers and finished Flagler's railroad for good.
Navigate day 1 in Google Maps ↗
The Turtle Hospital in Marathon, walk Pigeon Key beneath the Old Seven Mile Bridge, swim the deep cut at Bahia Honda, then key deer at dusk and a slice at the No Name Pub. Overnight Big Pine.
A working sea-turtle hospital in a converted motel, running rescue, surgery and release since 1986. Book the tour; you will meet the patients.
The railroad workers' island village sits under the original Seven Mile Bridge; the restored old span is now a two-mile walk over open ocean. Golden hour here beats any postcard.
The Keys' best natural beach beside the dramatic broken arch of Flagler's Bahia Honda bridge. Swim where the ocean and the Gulf trade water.
A dollar-bill-papered pub hiding down a back road since the 1930s, in the middle of the National Key Deer Refuge. The knee-high deer own the right of way at dusk.
Navigate day 2 in Google Maps ↗ · via The Turtle Hospital
The last stretch of blue to Mile Marker 0: Hemingway's six-toed cats, the Southernmost Point line, and a green flash from Mallory Square. Drive back or fly out of the little island airport.
The end of US 1 at Whitehead and Fleming. The sign gets stolen constantly, the photo line never shortens, and the atlas officially runs out of South here.
The Keys' best natural beach beside the dramatic broken arch of Flagler's Bahia Honda bridge. Swim where the ocean and the Gulf trade water.
A dollar-bill-papered pub hiding down a back road since the 1930s, in the middle of the National Key Deer Refuge. The knee-high deer own the right of way at dusk.
Navigate day 3 in Google Maps ↗ · via Bahia Honda State Park, No Name Pub & the Key Deer
The Overseas Highway is a 3-day trip of about 210 miles.
It starts in Miami.
It chains The Overseas Highway.
Day 1: Miami → Islamorada; Day 2: Big Pine; Day 3: Big Pine → Key West.