Over the years, Key West has welcomed pirates, hippies, Hollywood escapees, world-class drag performers, and Jimmy Buffett—and this funky town continues to be a haven for unconventional types. It's also a tourist trap, especially on the main drag of Duval Street, which seems to be all souvenir shops and frat bars. However, as the southernmost city in the United States, Key West escapes the mainstream just by dint of its geography. Its legendary citizens include Ernest Hemingway, whose house is now a museum with approximately 50 pet six-toed cats, and Mel Fisher, a treasure hunter who discovered the Atocha, an authentic sunken treasure ship, just a few years before his death. His family now runs regularly scheduled salvage/treasure dives out to the Atocha.

The waters offshore Key West offer great diving, fishing, and sailing. Favorite day trips include Sand Key, the Dry Tortugas, and, recently, the artificial reef of the scuttled Hoyt S. Vandenberg. Come back by sunset so you can appreciate Key West's famous (and free!) Sunset Celebration, held nightly weather permitting in Mallory Square.