Road Trips to Remember: Key West | Outtraveler
Troy Sivan
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Road Trips to Remember: Key West

?We arrived in Key West and occupied a two-room suite on the top of the Hotel La Concha, and it was there that I really began to get Streetcar into shape. It went like a house on fire.? Thus begins one entry in the diaries of Tennessee Williams, one of Key West?s more enthusiastic fans, but not by any means the only one. La Concha is still there on Duval Street, the thrumming heart of this two-by-four mile rock -- and the most liberal, laid-back, and gay-friendly destination in the country. Locals call it the Conch Republic, having declared themselves independent in 1982 (a bit of hokum that Hemingway would have loved), and conch is what you?ll eat if you?re smart about it (try the cracked conch sandwich at B.O.?s Fish Wagon, 801 Caroline St.). But first park the car -- it got you here, and it will get you back. For the rest of your trip, it?s bikes and kayaks all the way.

Two of the island?s best gay guesthouses are more or less adjacent, on Fleming Street. Alexander?s, a colonial-style white wood house, all verandas and lush foliage, is elegant and low-key; the men-only Island House is a wilder affair -- clothing optional, with amiable staff who will arrange to get you a bike. Once they do, cycle to Hemingway?s home and say hi to Joan Crawford, Spencer Tracy, and Gertrude Stein -- three of the 60-some cats that inhabit the house, many with six freaky toes instead of five. Even if you didn?t read A Farewell to Arms, which Hemingway wrote there, the house is wonderfully evocative.

One block over on Duval, grab a rosemary roast beef sandwich from Croissant de France for the dolphin safari -- a three-hour trip of dolphin spotting and snorkeling. It?s a bad day if you don?t see barracuda, sting rays, and spiny lobster down there. If you?re good, chatty Zimbabwe-born captain, Gary Stanyer, will hand you a slice of pineapple before you clamber back aboard. Hold it underwater and watch a barrage of fish strip the rind clean. It might be the most thrilling thing you do all day -- unless, that is, you find yourself at 801 Bourbon, for Sunday night?s drag queen bingo. Potty-mouthed Sushi and Gugi Gomez would eat those fish alive. Dolphins, too.

More Road Trips:

New York: An upstate culinary crawl

Chicago: A dog day afternoon in the Windy City

Napa: Massages and Meyer lemons in wine country

Tags: Florida Keys
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