7. Fantasy Fest

The Buzz -- This 10-day festival draws big crowds each year, providing a boon to local businesses during a time that, once upon a time, saw Key West almost devoid of tourist traffic. Highlighting the city's creative energies, Fantasy Fest features a full slate of themed parties – from clothing-optional partying at the Bull & Whistle's rooftop bar to the Caribbean-themed Goombay soirées in Bahama Village. Parades down Duval Street, a pet masquerade, costume shows, a street fair and various art competitions round out the late October fun. For specific times and events, keep your eyes peeled for the program published prior to each festival in "The Key West Citizen." The website is also a good source for dates and locations. Some bars have a cover-charge for the parties and others don't, so plan accordingly.