Key West

This laid-back tropical island is the perfect gay getaway

Among famous gay resort towns, Key West has always stood out for its sheer embrace of total relaxation. This laid-back tropical island in the Caribbean, closer to Cuba than to mainland Florida, is without pretensions. People rarely worry about what time it is, dress is casual and colorful, and the party scene is friendly and easygoing. Key West is neither fancy nor especially urbane – it’s just a great place to laze in a deck chair on a bougainvillea-choked lanai, browse for beachwear and souvenirs along the main drag, Duval Street, or relax on a restaurant patio noshing on raw oysters and sipping mango iced tea or mojitos.

For a seasonal tourist town, Key West has plenty to offer when it comes to dining and nightlife. Few places draw more raves for outstanding food than Alice’s Key West, where chef Alice Weingarten serves some of the most inventive food in town, including delicious smoked-salmon Benedict at breakfast. A departure from Key West’s predominant laid-back tropical look, Square One is a sophisticated restaurant with white table linen and fine china. The regionally inspired Continental cuisine includes escargot baked in a crepe with fresh spinach, garlic, feta, and a tomato beurre blanc. It’s a top choice for a romantic evening.

One of the better Italian restaurants in town, and also one of the gayest, La Trattoria has two dining rooms – the smaller one romantic and intimate, the larger better for groups of friends. The straightforward cooking draws high praise for such tasty creations as local shrimp sauteed with garlic, fresh tomatoes, and herbes de Provence in a white wine, lemon, and butter sauce. One of Duval Street’s true places to be seen, Mangoes brims with colorful sorts. The composed salads, pastas, and grills – all with nouvelle Florida touches – are commendable. Consider rib eye steak Caribe (pan-charred with tamarind steak sauce and yucca).

Seven Fish, which occupies an old luncheonette and has a sleek, sophisticated interior, serves seafood-oriented bistro fare, such as crab and shiitake mushroom ravioli. The slogan at Mangia Mangia is “pasta to the people,” a philosophy reflected by the many varieties of heavenly homemade pasta, all fairly priced. The painstakingly preserved building has a lovely, quiet garden and redbrick patio in back. You’ll need luck and persistence most nights to get a seat at Camille’s, a small storefront bistro, but the friendly vibe and down-home comfort food are worth the trouble. Expect good salads and sandwiches, such as Philly cheese steak, and delicious pancakes for breakfast.

For arguably the best sandwiches and wraps on the island, try Lobo’s – the oyster roll with cheddar, bacon, and basil tartar sauce is a stand-out. El Siboney is a zero-atmosphere eatery – the place in town for humble, stick-to-your-ribs Cuban fare. Rickety tables are set with plastic tablecloths and paper napkins. Try such Havana specialties as conch chowder, garlic chicken, stuffed shrimp and crabs, platanos (plantains), and a sweet flan to top it off. As for traditional Cuban sandwiches, tiny 5 Brothers Grocery – on a side street in the historic district – serves the best around.

Much of the gay social activity in Key West takes place at resorts, some of which provide refreshments and snacks to guests during the afternoon and early evening. A handful of properties have bars open to the public, among them the ultra-cruisy, all-male Island House, which also has an excellent restaurant.

Most the town’s gay bars are along Duval Street. Here, the La-Te-Da guest house has a poolside bar, an intimate piano bar, and the Treetop Cabaret Lounge upstairs. Down a few blocks, the New Orleans-inspired Bourbon Street Pub is a cheery place with a small bar up front with cocktail tables, a larger outdoor bar in back (along with a lively pool area and hot tub), and video screens galore. Many nights you can catch awful (but still entertaining) drag shows on the stage in back. The same owners run the lovably raffish 801 Bar, Key West’s definitive neighborhood hangout since the 1970s. There’s almost always a crowd of gossipy locals around the bar. The adjacent One Saloon caters mostly to leather-and-Levi’s types and is reached through 801’s back door. Aqua Nightclub is best known for its raucous drag shows, which are headlined by the in-house drag troupe, the Aquanettes. This lively place also has strippers some nights, an impressive dance floor with high-tech laser-and-sound shows, and a cozy video bar.

Key West has a number of inns that cater either exclusively or predominantly to the gay market. One of the best is Alexander’s, a long-popular gay resort with the relatively unusual policy of being both clothing-optional and welcoming to both women and men. This makes Alexander’s ideal for gay guys traveling with lesbian friends, or for any queer vacationers who enjoy a mixed-gender atmosphere. The effect is that the mood around the pool and hot tub tends to be less cruisy than at single-gender resorts. Aromatic tropical flowers, sundecks, rattan and wicker furnishings, and sparkling tiled bathrooms impart Alexander’s with a classy but casual look.

Most of the town’s men’s resorts are along Fleming Street, the Historic District’s main drag. Here you’ll find Equator, which has plush rooms with contemporary Caribbean-influenced furniture. Designer fabrics, feather pillows with comforters, Mediterranean-tile floors, large closets, and excellent sound insulation add to the comfort of each unit. The tradeoff is that the Equator’s grounds, although nicely landscaped, are smaller than at some of its competitors; there’s a compact pool and an oversize Jacuzzi tub.

For years the sprawling Island House – a former cigar factory on the eastern edge of the Historic District – was synonymous with sex, sleaze, and shabbiness. It’s still synonymous with sex. But, happily, new owners have completely rebuilt the place, hired friendly and competent staff, and created lovely rooms with high-quality furnishings (all have VCR/TVs, refrigerators, safes, and plush linens). If you’re seeking a steamy ambience but also first-rate accommodations and a safe, friendly environment, the Island House is your dream come true. Amenities, all of them available 24 hours, include heated pool, indoor and outdoor Jacuzzis, gym, sauna, steam room, and erotic-male-video lounge.

Another all-male property with a somewhat cruisy vibe is the New Orleans Guest House, an attractive compound that’s above the Bourbon Street Pub, right in the center of the Duval Street action. Rooms are well-outfitted and attractively decorated, and rates moderately priced.

The Hyatt Key West Resort and Spa is freshly renovated and features elegant Floridian touches and luxury. It is an intimate resort that provides privacy and gorgeous views. Located directly on the water and offering activites such as parasailing, diving and sailboats. Guests can enjoy the nightlife and restaurants of Duval Street, which is only 3 minutes’ walk from the resort.

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