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Still Crazy for
Key West

Still Crazy for
Key West


What's most memorable about this 4-by-2-mile island? Pretty much everything.

Two summers ago I went to Key West, Fla., for the first time, and honestly I've wanted to go back ever since. It's not like we often go back to reminisce on this site, but pictures keep coming to mind. For instance, my room at Pearl's Rainbow.

When I stepped off the pint-size plane at the Key West airport in July 2004 I was on the job, being shown the gay and lesbian sights so that I could recommend the island to Advocate readers. Nice work if you can get it, you may say--and indeed it is. But just between you and me, not every site that's said to be charming actually charms. And making up pleasantries for days at a time can start to feel like very heavy lifting.

I mention this now because at the time I wasn't sure I wanted to stay in a women-only hotel. So sue me: I stereotype as much as the next dyke. I was picturing something genteelly underfunded and overpoliced. Like that lesbian-owned bed and breakfast I once visited that had little brass signs all over: "Please do not sit on the eiderdown." "Please do not put jiggle the handle on the toilet." Hoo-hah. Party time.

Pearl's Rainbow is nothing, nothing like that. It's luxe to the perfect degree--no expense spared, yet not so formal you want to tiptoe. The fixtures are handsome, the towels thick, the air conditioning fierce, the staff queer as queer can be. It's bliss. The main building started its life, like many in Key West, as a cigar factory. (Remember, Key West is just 90 miles from Cuba. The whole time I was there I saw planes and helicopters circling a point on the horizon headed, I was told, to Guantanamo Bay.) At the rear an extravagantly landscaped patio shelters two pools, a hot tub, and a laid-back bar where they'll grill you a burger whenever you want. I watched women arrive and, over the next few days, melt into puddings of lesbian contentment. One of the staffers told me that women cry when they leave and go back to their everyday lives. I believe it.

Pearl's: Something marvelous

So, two years later, I want to send a continued shout-out to Pearl's proprietors, Heather Carruthers and Leslie Leonelli. If you're a lesbian looking for a wonderful time away, call these women and get a move on. They've created something marvelous.

Not to be all grrrl-centric--if you're a guy visiting Key West there are a number of gay lodgings where you'll feel at home, in your clothes or in the altogether. Before I ever arrived, my delightful gay tourism contact, Steve Smith, assured me that there's no friction on Key West between gays and straights. That point was repeated by Carol Shaughnessy, the gracious (hetero) PR rep assigned to facilitate my stay.

I mean, come on, you think to yourself when you hear that kind of thing. But a few days later, I was well on the way to being a believer. Gay and straight, Key West puts out some major hospitality. (More shout-outs to realtor supreme Martha Robinson and lesbian scooter pilot Laurie Thibaud.)

Another place I keep wishing to revisit is Subtropic Dive Center. After a morning refresher course with unflappable instructor Jan Henry, I got underwater for a reef dive, cruising along at an easy depth and surrounded by a riot of underwater life. Favorite "gotcha" moment: When I first got down to the bottom, I swiveled my head and found I was face to face with a cobalt blue fish the size of a bathtub. I laughed so hard I shipped a little water in my mask. The fish blinked and swam off.

Other major hoots: The Gay Trolley Tour, which kicks off every Saturday at 11 a.m., mixes lots of humor with a considerable helping of gay pride. At Alice's Restaurant, I had one of the best meals of my life and got to say so in person to Alice herself, who appeared in a leopard-print toque. La Te Da, the pleasingly upscale hotel-restaurant-cabaret-bar that dominates the gay end of main drag Duval Street, was perpetually filled with tanned and windblown gay folk, tourists and locals, sharing vital dirt and powerful libations.

La Te Da, the pleasingly upscale hotel-restaurant-cabaret-bar that dominates the gay end of main drag Duval Street.

Speaking of La Te Da, drag is huge on Key West. We forget out here in Los Angeles how freeing drag can be for a crowd of queer vacationers who spend 51 weeks of the year trying to act straight. One of my favorite mental snapshots is of a vacationing crowd of lesbians at the dance club Aqua, genially stuffing dollar bills into the G-string of a burly drag queen lip-synching novelty songs like "Hot Pussy." John Waters would have been proud. On the other end of the drag spectrum, La Te Da's Christopher Peterson is the island's Eleanora Duse. He does his own singing and at least a dozen quick changes too, and the night I saw him he had the audience on its feet.

There's lots more to tell: Hemingway's house--that scandalous old homophobe--and Tennessee Williams's too. A visit with gay travel pioneer Hanns Ebensten, who received me with his majestic black cat in his arms. Everywhere, tropical vegetation that flourishes in gigantic proportion, like something out of a dream. Homemade ice cream in Cuban flavors. The gay-owned Key West Butterfly Museum, a spectacular experience that deserves a column to itself. And finally, the fun of tooling around the island on a rented scooter, zipping along fast enough to cut through the humid air and become your own cool breeze.

30 Years of Out100Out / Advocate Magazine - Jonathan Groff & Wayne Brady

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Anne Stockwell