Key West is the southernmost point in the continental US, a quirky island of conch houses, roosters and pastel bars, with snorkeling, fishing and sunsets that draw crowds nightly. Winter is the best season; hurricane season runs June to November.
Good to know
- Winter weekends are packed; book flights and rooms early.
- Duval Street is for bars; stay on a quieter side street and rent a bike.
- Hurricane season can close roads and the airport; buy flexible tickets for fall trips.
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Places the planner can use
Mark places as a must or something to skip. The itinerary is built only from this list; ★ marks the destination’s highlights.
Nightly celebration with street performers, vendors and a Gulf sunset.
Bars, live music and the famous Sloppy Joe's.
Writer's former home with six-toed cats and a lush garden.
Photo stop at the buoy marking the southern tip of the continental US.
Climb 88 steps to the top of the lighthouse for sweeping views over the island and the Gulf and Atlantic.
Compare slices at Kermit's or Blue Heaven; the best are tart and on graham crust.
Small aquarium with touch tanks and shark feedings.
Catamaran cruise with drinks and the island skyline.
Ferry or seaplane to Fort Jefferson on a remote island with clear snorkeling water.
Half-day boat trips to the only living coral barrier reef in the continental US.
Famous patio with roosters wandering the tables and lobster Benedict.