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Key West Gay Travel Guide
If you want year-round tropical weather, an utterly laid-back pace, quaint shopping and dining, and a friendly (and occasionally intense) gay nightlife, it doesn’t get any better than Key West, baby! This almost-Caribbean paradise sits as the southernmost point in the continental U.S., and it is tradition to rent a convertible in Miami and make the three-hour scenic drive which island-hops its way down across some of the world’s longest bridges. (Or you can fly into the island’s small airport from a few gateway cities.) Once there, it’s easy to walk to all the popular areas, or you can rent scooters (more popular than you’d think!) at any of a dozen agencies. Though life in Key West is more about relaxing than sightseeing, you have to check out the Hemingway House, haunt of the legendary writer and now home to an appalling number of 6-toed cats. It’s also traditional to take your picture next to the Southern-Most Point. Key West has always been a haven for quirky individuals, evidenced by the morning of April 23, 1989 when Key West seceded from United States of America and declared itself a sovereign state, the Conch Republic, all because they didn’t like what the Immigration and Customs officials were doing with roadblocks. Officially they’re still part of the U.S., but they don’t act like it, and occasionally declare war on countries who they feel are making stupid decisions. However, as life in Key West is supremely laid-back, it’s doubtful they’d find anyone to fight. Like Provincetown or Palm Springs, Key West social life centers around the numerous gay guesthouses, and though visitors do venture out for morning shopping, and evening dinner and clubbing, most of the time is spent around the pool at the guesthouse. Each night, it’s traditional to either watch the sunset with the masses at Mallory Square, or to book a sunset cruise with Captain Steve on his big gay boat Blue Q, with complimentary cocktails and a friendly crowd. For now, Key West is a liquor-friendly island, and you can walk down Duvall Street from bar to bar with a beer or cocktail in your hand. Snooty island residents are trying to change that, however, so ask at your clubhouse before you pop open a cold one and head for an afternoon stroll. Outside of summer PrideFest, the winter holiday season is the busiest time for Key West, so make your plans early. Spring Break brings the young crowds, and summer is the next busiest season. Fall (hurricane season) is typically quiet. Each Thursday, a local cruise charter hosts a Women's Champagne Cruise for Lesbians.
Gay Key West Bars, Restaurants and Clubs
Nightlife is not explosive on Key West like it is further north in Miami and Ft. Lauderdale. The few dependable spots include 801 Bourbon, which has been a Key West institution for over 30 years. Bourbon Street Pub is a little more hip and lively, and has a small dance floor. Kwest Men has go-go boys and a long bar. Pearl’s Patio Bar is where lesbians congregate, and Saloon 1 is a tiny leather hangout.
There’s only one gay club in Key West, and that’s Aqua. It’s not much more than a modest dance floor surrounded by two bars, and the dance floor is rarely full. This isn’t a dancing island. Most everyone crowds around the bars and spills out into the streets, chatting and flirting. Because of its open-air atmosphere, it draws a significant hetero crowd as well, but everything is very relaxed and friendly. On Sundays, everyone heads to Tea Dance at the Atlantic Shores Resort, probably the largest gay event of the week.
Key West has some of the most stellar cuisine in the country, and most restaurants are utterly casual and have patio-dining. The only gay-owned restaurants currently are Magnolia’s, with great breakfasts and American-style lunches and dinner (best Bleu Cheese dressing on Earth!) and Pizza Joe’s. Quite popular with the gay crowd, if only for the name, is Crabby Dick’s with a mouth-watering (but overpriced) seafood selection. La Trattoria is excellent for romantic Italian. Camille’s is a local institution, with its naughty décor and menu quotes which liken their dining experience to something under-the-covers. Camille’s is where everyone meets for breakfast, and enjoys adventuresome dinner fare. The host at your guesthouse will arrange to have lunches brought to you, poolside, and will make reservations for your dinners if you’ll tell him exactly what you’re looking for, and what you want to pay.
Gay Friendly and Gay Key West Hotels
Key West offers a number of gay guesthouses, many of them clothing-optional, and each catering to a different crowd. It’s important to do your research before you choose a guesthouse, as you’ll be spending 80% of your time there. We begin with the Island House, voted the best gay resorts in the world, by readers of OutTraveler. If you don't stay there you can purchase an Island House Day Pass and still experience the frolickings of this amazing gay guest house. The Almond Tree Inn, not exclusively gay, but attracting a high percentage of discerning gay and lesbian clients, as does Andrew’s Inn, located just across the brick wall from Hemingway’s home, and the Blue Parrot Inn. Other exclusively-gay accommodations include, Heron House is a gay-friendly guesthouse offering a luxury atmosphere to discerning gays and lesbians, as does Alexander’s. Big Ruby’s welcomes women, as well as men, and owns other gay properties in France and Costa Rica. Pearl’s Rainbow is the premier lesbian-only property on the island. Beyond these properties, we get into the clothing-optional guesthouses, which are probably not as naughty as you think they sound. The New Orleans House is the only guesthouse right on Duval Street, at the heart of the gay scene. Coconut Grove is a popular standby which attracts a more mature following. Equator Resort is a newer hostelry, blending upscale amenities with the laid-back atmosphere of clothing-optional. Lighthouse Court, just a block off Duval Street, sits underneath a famous lighthouse, and has both an on-site café and video bar. Oasis Guesthouse and Coral Tree Inn, jointly owned, sit opposite each other on a residential street in Old Town, and guests can use the facilities of both…Oasis offering a more playful, cruisy environment with two pools, a massive hot tub, and a variety of sunning decks, and Coral Tree being quieter and more luxurious. Island House for Men, which was hailed as The Best Gay Men’s Resort in the World by Boyz Magazine, is an even more intense guesthouse, and doubles as a sauna selling day-passes to guests of other properties.
If a genuine hotel is more your style, you can try the famous Atlantic Shores Resort. It attracts a good mix of gay and straight patrons, and its clothing-optional seaside pool and café are open to everyone (though it’s a bit of a hike from the Old Town and Duval Street areas). For something more central, try La-Te-Da, a famous hotel right on Duval Street, which offers chic accommodations to a mostly-gay clientele. For something a bit more modest, try the Heartbreak Hotel, without the pool and hot tub bragged about by other properties, but smack dab in the middle of gay Duval Street.
Call an edirp.com gay travel specialist at 1-888-EDIRP-EZ (1-888-334-7739) or (214) 520-0345 (U.S.) to book any of the hotels mentioned above. Any hotels with links may be booked via our secure online booking system.
Key West Gay Pride and other Gay Events
PrideFest is Key West’s summer Pride event, the first week of June, and draws everyone from Miami and Ft. Lauderdale. (So make your reservations a year in advance!) In the fall, FantastyFest is almost as popular, and is held around the first of October at the same time as WomenFest, a sort of lesbian circuit party. <P style=" FONT-SIZE: 10px; COLOR: black; LINE-HEIGHT: 130%; FONT-FAMILY: verdana,arial,sans-serif?>Travel guide by Benjamin Starr, a travel writer who claims the entire world as his home. When he's not at home, he can sometimes be found at a residence in Dallas, Texas. To contact Ben, email him at benjaminstarr@sbcglobal.net.
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