There are gay-friendly towns. There are really gay-friendly towns. And then there’s Key West.
Looking around the cramped aluminum puddle-jumper that people-moves revelers from the Miami airport, I am struck by the prevalence of "types" on this aircraft, of which there are two. First, the pros: laconic gay guys, primed for a weekend of sun-kissed debauchery; and second, the amateurs: loud and obnoxious New Yorkers (redundant?) who think nothing of yelling "Where’s the beer?" and "Let’s get this party started!" and "Vinny! Oh my gawd! I can’t believe we’re almost there!!!"
Even the staid-looking man in the windowpane sports coat doesn’t seem immune to the infectious rowdiness.
I’ve seen such behavior in the movies — usually in the minutes right before the high school football team crashed into a mountain — but to see (and listen) in person as people shout into their cell phone and act as if Shangri-La has almost arrived is something else entirely.
Such is the effect of Key West.
Alighting from the air on the furthest landmass in the continental U.S. — a little spit of rock and powerboats at the tail end of the Florida Keys — you’re struck by how tiny and Southern-small-town-like this most famous key is. This is where Hemingway and Truman called home even before college kids discovered they could get wasted here to the strains of Jimmy Buffet. It’s also where the gay community has long been a potent political force: It boasts the country’s first openly gay mayor, and there are gay council members and chief of police right now.
Locals will tell you it’s not as gay as it once was. Leathery, emaciated, cold-hating New England snowbirds have transplanted themselves here for years. It’s almost become a gay zoo, where queer entertainment is paraded around for spectacle’s sake.
But if an entire city can have a camp factor (Vegas isn’t camp; it’s kitsch), Key West may be it. There’s irony around everywhere, a winking but lackadaisical attitude toward everything. You wanna walk around in a Speedo and pink boa while holding hands with your girlfriend and drinking a mojito? Have at it. The only thing that raises an eyebrow around here is a facelift.
The best way to move around the island is by stopping by the Moped Hospital, a scooter-rental service chocked with cute, sweet, funny and helpful young men who will hook you up with some wannabe Vespas. After a few minutes’ orientation, it becomes second nature to toot down Duval Street, the main touristy thoroughfare, and through the backroads where you can find accommodations, dining and plenty of activities to fill a weekend or a week.
Gay guesthouses used to populate the town like anthills after a rainstorm. The AIDS epidemic eviscerated much of the gay community (the highest death rate per capita of any city in the country at one time), but it survived and has continued to prosper.
There are currently nine gay-specific properties, including Pearl’s Rainbow, a women-only green-certified lesbian resort with 38 rooms and a spacious pool and bar area (men are jealous they can’t stay here); and two co-ed inns: Alexander’s Guesthouse and Big Ruby’s Guesthouse. Ruby’s — large and tropical — serves great food. But for many gay male travelers, it’s the clothing-optional all-male resorts that pack a lot of appeal.
The most famous — not to say notorious — is the Island House. Huge, with multiple pool-and-spa areas and a very cruisy vibe, it has a nice cafÃ© and bar, plenty of guestrooms and a 24-hour sense of fun.
Island House sits at the far end of Fleming Street, well afield of the bustle of Duval; bunched closer together on Fleming are four (clothing-optional) guesthouses with their own appeal.
The Equator’s smallish size — 15 rooms — belies its charm, with off-the-pool cabanas and a friendly staff with complimentary breakfast and happy hour daily (and porn playing in the flat-screen above the bar). Next door sits the Coral Tree Inn, a restored 1892 mansion, and across the street, the Oasis Guesthouse and Coconut Grove provide quaint accommodations (a rooftop deck at Coconut Grove; two pools at Oasis).
There aren’t tons of clubs in Key West, but for a city its size, more than enough to keep you entertained with a variety of options (virtually all along Duval). Lesbian-owned Aqua welcomes a mixed gay-straight, male-female crowd to its high-tech dance floor.
801 Bourbon Street (and its sister club, the Bourbon Street Pub) creates a Big Easy feel with its anything-goes approach to revelry. The bar tops are crowded with nearly-naked muscleboy dancers and a massive outside garden with beachy cabana bar bustles with excitement. (There’s even a clothing-optional guesthouse upstairs.) Saloon One, a sleazy (in a good way) leather bar attracts a rough crowd, but — ummm —a "friendly" one. The same is true of Kwest, a dark, porn-playing slip-in pub and cruise joint.
Straight and gay happily mingle throughout Key West, but nowhere more gleefully than at La Te Da, a cabaret, restaurant, hotel and club that hosts one of the top drag shows in the country and is simply abuzz with good cheer any time of day.
Dining is especially gratifying here. Mangoes serves exceptional food (like a lobster stuffed with blue crab) on its outdoor patio. Key West iced tea — a pink lemonade with punch — gives Long Island’s version a run for its money. The food at Azur is elegant and glamorous even in a causal town like Key West. Grab a continental breakfast at Croissants de France or a more diner-y meal at Harpoon Harry’s.
Even gays may not live by pools, food and parties alone — at least not all on land. Key West offers plenty of daylight adventures, too.
For an informative street tour, hop on the Gay Historic Trolley, a motorized jaunt through the city’s narrow-streeted neighborhoods that fills you in about the many gay celebs who have called this home, as well as why all the cemeteries are above ground. Hemingway House, with its famous menagerie of cats, and the Truman White House are mainstream tourist traps but completely fascinating in their own right.
For more seaworthy expeditions, there are a few don’t-miss options. The Blu Q is a men-only, clothing-optional schooner trip out to some shallow island off the coast. You can go snorkeling and enjoy an in-the-water lunch (including beer) on this five-hour adventure. (Venus Charters offers a similar trip for women.) For a more family-friendly version, a sunset cruise provides breathtaking views of the key from the sea.
A guided Jet-Ski tour around the island makes for a thrilling workout and the chance to frolic among the seaweed. It’s about as fun as water sports get. Even in Key West.
It’s just a fantasy
How’s this for sweetening the pot during a down economy: Key West’s annual week-long Fantasy Fest occurs each October, right around Halloween — which is officially the off-season for Key West but when the temperatures still often hover in the 70s and low 80s.
It kicks off with the Goombay Street Festival, which stretches down Petronia Street for blocks and blocks, with skewered foods and trinkets of all kinds for the buying. There are parties aplenty throughout, but it culminates with the main social event of the season, the Headdress Ball — a costume party and runway show that’s as fabulous as the Vegas strip.
Fantasy Fest runs Oct. 23â€“Nov. 1. The Headdress Ball takes place Oct. 27.
For more information on Key West, visit GayKeyWestFl.com.
This article appeared in the Dallas Voice print edition September 18, 2009.
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