2. Key West, Fantasy Fest
There is never a sleepy, uneventful day in Key West, Florida. At 2 miles wide and 4 miles long, the island has more bars per capita than anywhere in the U.S. American writers Ernest Hemingway and Tennessee Williams enjoyed the legendary nightlife on Duval Street, and gonzo journalist Hunter S. Thompson coined the phrase “When the going gets weird, the weird turn pro” when he was holed up on the island on the 1970s. Key West has a reputation for being a liberal, laid-back, and year round party town, but the revelry reaches an apex during Fantasy Fest, a 10-day celebration at the end of October.
First held in 1979, Fantasy Fest includes masquerade balls, costume competitions, Aids fundraisers, drag queen contests, body painting, and a one-of-a-kind parade. The event is like the combination of Mardi Gras and San Francisco's Gay Pride Parade. Over 100,000 people attend Key West’s glittery bacchanal every year, and it attracts everyone from swingers and exhibitionists to those simply looking to delight in an adult’s only atmosphere.