Day 1: Key West Characters
When you’re talking Key West, the name Hemingway is bound to crop up. The author lived on there for more than a decade, in Old Town. This is also where President Harry S. Truman chose a getaway on Key West. Eisenhower and Kennedy also stayed at the house at 111 Front Street, which is open for guided tours.
Day 2: Conch tours and mansions
Jump aboard the Conch Train, a hit since 1958. The 90-minute train ride begins on Front Street and loops through Old Town Key West. Bone up on the island’s conch history at Heritage House, browse the Pirate Museum, and see treasures from the deep at the Shipwreck Museum.
Day 3: Dip your toe in the water
If you can’t decide where to start, the full-day Power Adventure combines a catamaran sail across the Gulf of Mexico, kayaking in the mangroves, parasailing, kayaking and snorkeling. Go for a cruise and view Key West from the water, or drink champagne on a romantic sail into the sunset.