Every evening is an event in Key West, as the fabled sunset celebration sees cobblestoned Mallory Square come alive nightly with jugglers, acrobats, beds-of-nails-lying-downers and hoop-jumping cats. Though cheesy, this is more like Stilton than bland cheddar. For a more concentrated Key West experience, come down December 31 for the New Year's Eve festivities; in March for the Conch Shell Blowing Contest, a 40-year tradition (it's more difficult than it looks); late April for the 10-day Conch Republic Celebration, in honor of the short-lived but festive independence of this would-be Caribbean nation; and late October for the Haunting of Fort Zachary Taylor, when the US Coast Guard gets the 'Isle of Bones' spruced up for a scary historical experience, followed by Fantasy Fest, Key West's massive Halloween bash.

Other classic Key West events include PrideFest in June, when the island - already a top destination for gay and lesbian party people from all over - hosts a fabulous party. Bearded gents won't want to miss July's Hemingway Days Festival, topped off with an author look a like contest, while kitsch connoisseurs simply must experience November's Pirates in Paradise festival, when locals transform the old boat harbor into a rollicking rumrunner reenactment.