Ernest Hemingway, Harry Truman, and Jimmy Buffett have all been crazy about Key West. What is it about this place? For starters, the atmosphere. Residents (who call themselves "conchs" and their island the "Conch Republic") share a last-stop-before-you-drop-off-the-world mentality in which personal freedoms, self-expression, a comfortable hammock, and a fresh margarita (not necessarily in that order) are measures of the good life.
But this is Florida, after all, so the sun-sea-sand visitor will feel right at home, with activities such as fishing (the island is home to one of the state's largest sportfishing fleets) and diving. The place has more than its fair share of history, from homes of the famous (Hemingway's 1930s abode is now a museum) to the Mel Fisher Maritime Museum, which displays some of the riches the famed treasure-hunter found in the wreck of the Nuestra Señorade Atoche, a 17th-century Spanish galleon that sank off Key West.
Downtown Key West is a whirl of art galleries and T-shirt emporiums, interspersed with a healthy number of watering holes. After a day by the ocean, you can join locals and visitors at Mallory Square for the daily sunset celebration. The entertainment - street musicians, jugglers, magicians - and the party atmosphere are reminders that life in Key West marches to no drum but its own.