Gay Vacations in Key West, Florida

Sunset celebration with Will Soto in Mallory Square in Key West, Florida
The sunset celebration in Key West, Florida, in Mallory Square (Bob Krist/courtesy, Florida Keys News Bureau)

Key West Highlights

  • Key West in summer is cooler than Miami. Thanks to constant ocean breezes sweeping across the island, summer temperatures rarely go over 90 degrees, with less humidity than Miami, too.
  • Book early for winter. Snowbirds flock to the island for winter high season, and many properties require a two- or three-night minimum. Prices can go through the roof.
  • If you have the time, drive. Flights take less than an hour on the extremely efficient small planes from Miami, but if you have time to spare, a three- to four-hour drive on the 159-mile Overseas Highway is a real experience.

The Conch Republic is at the end of the dramatic Overseas Highway that links the Florida Keys like a necklace dangling into the Caribbean. Key West has been fun-loving, rebellious, and ferociously unique throughout its history, and since the 1960s, it has been a tropical magnet for LGBT travelers looking for a mellow, free-for-all getaway. With mainstream mom-and-pop cruise ship passengers using the island as a place to simply buy T-shirts, some have claimed Key West is past its queer prime. But it still has dozens of gay and lesbian and gay-welcoming guesthouses (many in historic plantation-style buildings with sweeping porches and clothing-optional pools), plus bars and businesses that attract throngs of gay and lesbian followers to this day.

notprocessedcontentstorng/notprocessedcontentThe heaviest concentration of homo haunts is on either side of Duval Street (the Bourbon Street of Florida) in Old Town. But gays are everywhere on the island, which feels like a huge, sunny Castro. Nearly every weekend, the island is alive with street fairs, drag shows, leather parties, women's flag football tournaments, and special events for bears, nudists, bisexuals, and anyone else. And then there are the annual LGBT parties: Local gay hot spots band together from late February to early April to create Gay Spring Break 2007, with beach parties, toga parties, wet T-shirt contests, offshore cruises, and a huge street dance party in mid-March. Other big draws are Conch Republic Independence Day in April (with a mock sea battle), the nude-y Tropical Heat party weekend (also in April), Pridefest in June, Hemingway Days in July (complete with Ernest look-a-like contests), Womenfest in September, and the straight-popular but very queer Mardi Gras-style Fantasy Fest (around Halloween).

Sites worth visiting include the Harry S. Truman Little White House, where he spent much time. If you tire of the pool, head to "Liz Taylor," the gay name for queer-popular Fort Zachary Taylor Beach. Or better yet, go for a snorkel at the Key West National Marine Sanctuary, just a boat ride away. And every evening, locals and visitors gather at the docks behind Mallory Square (at the westernmost end of Whitehead Street) to applaud the deep orange-red sunsets.

Published: 16 Jul 2008 | Last Updated: 8 Aug 2012
Details mentioned in this article were accurate at the time of publication


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