The Sisterhood of the Traveling Pants: A Transcendental Guide to Key West

by Tony Phillips
EDGE Media Network Contributor
Monday Dec 26, 2011

I arrive in Key West, Florida, with the haughty air of most first-time visitors from residences they imagine to be much more cosmopolitan. But, less than 24-hours after touchdown, I am sitting on a rooftop patio in a deck chair with my pants off enjoying a key lime margarita in one of the many clothing-optional cocktail lounges that dot our nation's southern-most terminus. Just like that, Key West has done its trick.

And though it is technically just inside our borders, there are times when Key West can seem as remote as the Mamanucuan island of Monuriki where Tom Hanks took up with Wilson in the 2000 film "Cast Away." Upon boarding an American Airlines flight from New York, my single carry-on is promptly confiscated and gate-checked by a haughty attendant. Several hours later, landing at the tiny, Key West International Airport after 10 p.m. on a connecting flight, my bag is carelessly lost and not seen for days.

Just trying to locate a Key West pharmacy open after dark is problematic enough, but by day two of having no fresh clothes to wear, I actually begin to physically resemble Hanks' "Cast Away" character. The choices for my three-night stay are clear: either hole up in the hotel robe hoping the complimentary bottles of red wine keep coming or revert to wild type and hit the town. The commanding views of the Gulf of Mexico are tempting, but embarrassingly, a single back-issue of Vogue is the only thing that wasn't gate-checked, so I choose life.

And life on this sleepy key doesn't really rouse before noon; nonetheless, mine begins over an 8am breakfast with Lin Schatz, the general manager of the Hyatt Regency Key West Resort and Spa (601 Front Street, 305-809-1234), the property where I'm staying.

We enjoy a hearty breakfast at SHOR American Seafood Grill, one of the resort's two dining options. It's the last day of the summer breakfast menu, which featured items like sensible steel cut oatmeal and the fanciful sticky bun French Toast. Toward the end of the meal, a new addition to Hyatt's team, chef Dan Elinan, joins us tableside for a locally sourced honey tasting with offbeat flavors like saw palmetto berries and the ubiquitous key lime.

After breakfast, Schatz--a veteran who has worked at ten other Hyatt properties--leads a tour of the five story, 118-room hotel. Three buildings--overhauled with a $10 million renovation by interior designers Morrison Seifert Murphy in 2007--horseshoe a heated pool flanked by SHOR on one side and the resort's other dining option, the Blue Mojito Pool Bar and Grill, on the other.

Schatz begins the tour above SHOR in the Marquesa Room, the largest and most dramatic of the resort's three event spaces. The smaller rooms feature balconies and terraces, but the Marquesa pairs a white, trestle ceiling with airy skylights. The room's all-white palate has the good sense to get out of the way of the dazzling sunsets it frames nightly.

Schatz says the banquet rooms trade mostly in weddings. The resort will see about one hundred this year and even offers outdoor options on its beaches and pier, all with fully customizable menus. This focus on marriage and summer's "amour" packages, even the couple's massage suite in the spa, adds up to a resort that's definitely couple-friendly, but as a single person, I don't feel it's too in my face. I even appreciated how much catering to the newly paired, in contrast to extant families, cuts down on the screaming children quotient poolside.

On the outdoor path to the resort's cozy, living room-like lobby, Schatz bumps into his assistant, Bebe Clark, a "Conch" born and raised on Key West. She's feeding the resort's turtles, which live in one of two gender-appropriate ponds just off the lobby next to Odie, the resident parrot. Clark is taking care that Myrtle, the tiniest of the turtles, gets her fair share of the day's food. She explains that the island is also populated by feral roosters, Cuban holdovers emancipated when Key West banned cockfighting in the 1970s.

Still, the wild birds divide the city. Local "chicken lady" Katha Sheehan provided a "safe house" for fowl out of her Duval Street Chicken Store before she relocated to Homestead, Florida, a Miami suburb that's a gateway to Florida's Everglades. Other residents supported the city's relocation program, which exported about one thousand chickens before it was shut down. Clark's complaint that the roosters "scratch up all my mulch" clearly puts her in the latter camp.

Schatz concludes the tour, pointing me out of the resort and around the corner where I rendezvous with Elyse Eisen, the trip's liaison from the Cheryl Andrews Marketing Communications P.R. firm, and two other writers she has on the trip. We meet on the back patio of Croissants de France (816 Duval Street, 305-294-2624) just off Key West's honky-tonk main drag. This French bakery is a local institution that was almost wiped out by the one-two punch of a 2005 fire and the 2006 Hurricane Wilma. The patio is part of a new "bistro" addition to the tiny complex, which serves not only breakfast, lunch and dinner, but also a selection of cakes, including erotic ones, out of their bakery.

After lunch, Eisen introduces Steve Curry, the fabulously gregarious guide for the Gay & Lesbian Historic Trolley Tour (Saturdays at 11am only from the parking lot on Simonton Street between Angela and Southard Streets, 305-294-4603). Key West measures just two miles by four miles, but is so packed with history that it's a perfect candidate for guided tours. And they abound. Each one has its various strengths and weaknesses. There are bike tours and a number of evening ghost tours.

The Old Town Trolley Tour (Mallory Square, 305-296-6688) is informative and a great choice if you're pressed for time as they offer a "hop-on, hop-off" option. Sheila Cullen, the guide on the Conch Tour Train (303 Front Street in Mallory Square, 305-294-5161), nearly had a heart attack when a French-speaking tourist hopped off her moving trolley. However, she is so well versed in the island's native flora, that taking her tour is a must for anyone with an interest in Key West's more than 600 species of plants or for people who just like hearing the word bougainvillea.

But for 75 minutes of good dish, Curry cannot be topped. Or maybe he can, and he's happy to boast about it on the trolley's PA. He's as want to use the device to indicate cute boys in the street, who, of course, can hear him as he is pointing out the island's rich queer history with it. The main highlight of this tour is Tennessee Williams' clapboard Bahamian cottage at 1431 Duncan Street, which the playwright purchased in 1949 and called home until his death in 1983.

All of the other tours point out Key West's tallest building, La Concha Hotel (430 Duval Street, 305-296-2991), where Williams is rumored to have penned the first draft of "A Streetcar Named Desire," but Curry has the exclusive on the private residence, where much of the 1955 Oscar-winning film version of his "Rose Tattoo" was filmed. Curry explains Williams' desire to live in Key West in his signature style, deadpanning, "He loved seamen."

Other queer highlights include poet Elizabeth Bishop's 19th-century eyebrow house at 624 White Street. Eyebrow architecture is unique to Key West and buries the second story windows under a long, sloped roof in a primitive attempt at climate control. Bishop purchased her home in 1938 with her lover Louise Crane and lived there for the next nine years. She returned briefly in the 50s, only to write that Key West "wasn't the same."

Key West is over: a refrain for the ages. Still, Calvin Klein, Jerry Herman, Kelly McGillis, Terrence McNally, even Oprah, have all chased the dream, buying property on Key West even after Bishop declared it D.O.A. Curry is even able to wedge Key West's most famous booze and testosterone-fueled resident, Ernest Hemingway, into his queer paradigm. "His mother dressed him up like a little girl," Curry explains. It sounds like another of his tall tales, up there with identifying the local Fed-Ex man as his boyfriend, prompting someone to ask, "How many boyfriends do you have," Curry's reply is, simply, "Just the three."


(Key West travel feature continues on next pages...)

But it turns out he's absolutely correct about Hemingway's early childhood. And Hemingway's youngest son, Gregory, had gender reassignment surgery in 1995 so there's definitely room for "Papa" on the bus. Think of him as a slightly butcher version of Cher.

After the tour, the only time crunch of the typical Key West day was on: the race against the sunset. Tourists gather in Mallory Square for the "sunset celebration," which always ends in applause as the sun dips into the Gulf of Mexico. Locals meet at The Top, La Concha Hotel's rooftop bar, for a more civilized cocktail, but this evening Eisen's arranged a sunset sail on the 42-foot Gale Wins yacht (805-225-3069).

Captain Kelly Nelson and his lovely wife Gale welcome us aboard. Kelly navigates around Wisteria Island, a mysterious and uninhabited isle with a jagged, brushy coastline, while Gale pours hearty cocktails. Kelly says the island is at the heart of Key West's ongoing struggle with its homeless population and local crackdowns--compounded by the fact that it's sometimes hard to discern between resident's laid-back sartorial style and actual homeless people--have forced some of the key's homeless population onto the deserted refuge.

The next in a series of vivid contrasts that make up Key West is illustrated by the adjacent island around which Captain Kelly pilots. The navy constructed it as a fueling station during the Cold War, hence its name: Tank Island. In 1986, the government sold it, and in 1994, developer Tom Walsh, who also owns Westin Key West Resort and Marina, renamed it the more consumer-friendly Sunset Key.

The island's 48 single-family homes, none of which sold for less than $1.5 million, are reachable only via a ferry running out of the Westin Marina. And if you think a reservation at the island's Caribbean-tinged restaurant Latitudes (Sunset Key, 305-292-5394) is your ticket to finding Oprah's house, think again. Ferries will only be scheduled within a 15-minute window of your reservation. And if you're late for any reason, the Westin security team will shoot to kill.

By this time, we're far enough south of Key West to realize that for tonight, at least, sunset has been cancelled. I'm sprawled across the bow of the yacht with Kelsey Chauvin, a writer for Passport Magazine. We are deep into our cocktails and trying to agree on whether the puffy clouds low on the horizon are cumulus or nimbus. Eisen calls forward to tell us we're docking early and all three writers aboard make sad clown faces until she informs us we're merely relocating to a local bar where there'll be more cocktails.

Gale Nelson, a saint of a woman, fixes a fresh tequila sunrise roadie before I step off her namesake yacht and thank her by slurring, "Sunset: 3. Sunrise: 10." Before we know it, we're at the outdoor Schooner Wharf Bar (202 William Street, 305-292-3302), a large, grungy thatched-roof drinky hut at water's edge that hosts live music and three happy hours per day, the first of which commences at 8am.

Only halfway through Schooner Wharf's exotic daiquiri menu, we begin the trek down Duval Street. Foot traffic swells as the evening progresses, but it's still hard to imagine the 100,000 people that crowd Duval Street for major events like Halloween's Fantasy Fest or New Year's Eve.

We arrive at the northern Italian restaurant Antonia's (615 Duval Street, (305) 294-6565) a little past our 8pm reservation and are led to a long table in the rear of the restaurant. Our party had grown to about twenty people that now includes Lin Schatz and his boyfriend, Steve Smith from the Key West Business Guild and various other Key West notables including a beautiful promoter named Zach and a Brit ex-pat who is a dead-ringer for Yves Saint Laurent and holds court admirably at his end of the table.

Dinner itself is a blur of delicious homemade pastas, really good wine and Chauvin somehow talking me into splitting an order of escargot: a snail first for me, but I quite enjoyed them. Over coffee, Smith tells the story of accompanying local drag legend Sushi to last year's CNN New Year's Eve telecast where she is lowered annually from the roof of the Bourbon Street Pub (724 Duval Street, 305-296-1992) in a giant, ruby slipper.

CNN's John Zarrella asks what she was thinking during the descent and Sushi replies, "Thank God I'm not Gloria Vanderbilt's son." But Smith is tight-lipped about whether the drag queen meant Anderson (funny) or his older brother Carter, who plunged from the family's 14th story apartment window in 1988 (not so funny).

Instead of slipping an Ambien into the molten chocolate center of our chocolate fondants, Eisen laid out options for a post-dinner Key West drag show. The upscale choice is Aqua Nightclub (711 Duval Street, 305-294-0555) where the "world famous" Aquanettes perform their show Reality is a Drag, while the more down-market, downtrodden drags display the 801 Bourbon Bar and Cabaret (801 Duval Street, 305) 294-4737).

Naturally, we opt for the seediest possible and once we're ensconced at the corner of the bar upstairs at the 801, host Gassy Winds does not disappoint. This robust Key West newcomer of a certain age was a Fire Island protégé of Gusty Winds, but relocated to Key West in 2007. We were slightly disappointed 801's in-house legend Sushi wasn't on the bill, but enormously-wigged Winds more than held her own.

After the show, Chauvin has the good sense to recognize an evening with the potential to end in fresh tattoos and slinks home gracefully, but the rest of the group: Eisen, cute Zach from the restaurant, Jennifer Kennedy, a writer from Santa Barbara, California, and me soldier on into the night.

It's hard to say where the idea even comes from, but suddenly we're climbing stairs to the Garden of Eden (224 Duval Street, 305-296-4565), the aforementioned clothing-optional bar with no cover and an oddly frat house vibe. The place is in full swing when we arrive, but only about ten percent of the crowd in any form of undress.

That is soon remedied as, without much prompting, Kennedy takes off her top, I remove my pants and Zach goes fully and gloriously Monty. The last I see of Eisen, she is fully dressed at the bar with her head in her hands, as if silently asking herself how this happened. She slips out soon afterward without saying goodnight.

Though Kennedy is bonding with another topless patron over their mutual admiration for each other's breasts, it's time to go when I overhear the bleached-blonde tell Kennedy she lives in a trailer. As we make our way down Duval Street back to the Hyatt, there's an attempt to lure Zach to the pool. I'm lobbying hard for Kennedy to forego her lesbianism, just for one night, and at least make out with Zach. She seems willing to take one for the team, as it were, but Zach calls it a night when we somehow get lost on the way back to the resort.

With our bearings straight, we finally make it home and cajole the overnight reception staff into doling out more "welcome" Champagne. We take our last cocktails of the evening to the pool and doff our clothes once more. I'm not too sure what happens next, but I do know I wake very early in the morning with a remarkably polite security guard whispering, "I'm sorry, sir, but the pool is closed." My nude form is casually draped over the motorized chair meant to hoist disabled guests in and out of the pool.

The next morning, our 8am breakfast is pushed back an hour for humanitarian reasons, and as everyone assembles at the table for the rollout of SHOR's new fall menu, not a word is spoken of the previous evening's debauch, another unwritten Key West rule. The new menu breaks out into sections like "Instinctive" containing dishes like the fried egg and ham melt with Gruyere cheese and "Responsible" housing the hard-sell, gluten-free pancake.


(Key West travel feature continues on next page...)

Chef Dan pops up to make another in his series of table-side presentations, this time on whether locally-sourced food can indeed be labeled as such if it comes from the mainland. I joke that if there's one morning he's ever going to be able to move that pancake, this is it. He could guilt us into it on the responsibility issue alone. Eisen annoys him further by completely deconstructing his bagel and lox entry, ordering most of the dish to the side, and he walks away from our table.

I look at my watch, something that's rarely done on Key West, and by that, I mean wearing the watch, not checking it. Mercifully, it's time for my massage appointment. My head is pounding as I make my way up to Jala, the second floor spa. I'm told the name means water in Sanskrit, but when Doug, the bearded and burly masseur, opens the front door and I'm greeted by a blast of eucalyptus-based aromatherapy, I decide on the spot that Jala actually means Doug's Enya-infused man cave.

Obviously, my burgeoning reputation as a naturist does not precede me as Doug walks me through a series of complex commands on disrobing for the massage, but he does so in such soothing tones, he's already working wonders on my hangover. By the time I'm on the table, I'm literally putty in his hands as he magically erases an entire evening of poor choices. When we're done, Doug even has the temerity to execute the old palm tickle when I press a tip into his hand. Oh, Doug, you had me at "Would you like me to work on your buttocks today?"

Feeling slightly more limber, I transverse the island's shorter axis along Simonton Street and end up on the south side at the Casa Marina Resort and Beach Club (1500 Reynolds Street, 305-296-3535). Construction began on railroad magnate Henry Morrison Flagler's architectural gem in 1918, making it Key West's oldest resort. And its 311 rooms, recently renovated, along with the entire property, by new owners Waldorf Astoria make it the largest.

Flagler had to build a railroad from Florida's mainland to Key West in order to lure well-heeled snowbirds, but that's exactly what he did, even though locals branded the project Flagler's Folly. But it opened on New Year's Eve, 1920, with Flagler long dead, but playing posthumous host to several presidents, Rita Hayworth and the on-location cast of "Operation Petticoat."

I linger over a delicious lunch of conch chowder and a shrimp and watercress salad facing the resort's 1,000 feet of sandy beach, another rarity on this almost beach-free key. My chatty server Kerry is from Ohio, but relocated because she loves to snorkel and "there's not a lot of oceans there."

Her sister captains a boat and will often ring her up to tell her she "has to come out for the sunset." On the rare rainy day in America's only frost-free city, Kerry recommends the used bookstore Island Books (513 and a half Fleming Street, 305-294-2904) for its eclectic selections and browse-friendly staff.

Making my way back to the Hyatt, I stop off at the Key West Aquarium (1 Whitehead Street at Mallory Square, 305--296-2051), a remarkably ramshackle affair that was built in 1934 by the WPA and is showing every minute of its age. The tiny space is essentially a long, poorly illuminated corridor with grotty concrete tanks in the floor and fake fish suspended from the ceiling. Weirdly, it is one of Key West's dog-friendly attractions, but why would you do that to your pet?

Back at the resort, I freshen up for my first dinner at SHOR. Chauvin has already departed for the greener pastures of Brooklyn, but Kennedy and I compare massages at one of SHOR's outdoor tables that are in a prime spot for the evening's sunset. Eisen joins us shortly and then Schatz stops by for a quick hello, but winds up staying for dinner.

Everyone is extremely low energy and when Chef Dan pops up tableside again, insisting someone try his barrel fish wrapped in parchment paper, we are worn down. When he gets into the locally sourced sea creature's preferred oceanic depth, Schatz just orders it, defeated. Over coffee, Eisen suggests another Duval crawl as Kennedy and I collectively moan. Detailing plans for a quiet evening in, we say our goodnights.

Naturally, I capitalize on the early break to cash in my day pass voucher at Island House (1129 Fleming Street, 305-294-6284), the largest of Key West's many all-male, clothing-optional gay bed and breakfasts. It's owned by a local couple, Jon Allen and Martin Kay, who just finished a $2.5 million renovation using only local designers and contractors.

But their cheapest room is almost $200 a night in season, which creates some voodoo economics for the hot young things required poolside at this type of establishment. Enter the $25 day pass, available at any time and good until 8am the next morning, turning Island House in the Key West's de facto bathhouse.

I arrive on the early side and there isn't too much cruising in progress on the pool's large upper sun deck. I recline on a chaise lounge in the balmy night air staring up at the bright canopy of stars. I notice that life imitates art as the disco ball's tiny lights bounce off the lush, tropical gardens swaying palms around the pool.

It's my first transcendental Key West moment, the one way you really know the place is working, but the feeling dead-ends into marveling over how spotlessly clean everything is. Before long, I'm having a beer poolside at yet another clothing-optional bar. There's that slight tinge of being just one white towel away from the night before. Eventually a four-way of fit, older bears tromps into the erotic video lounge gamely as Chinese acrobats. They use the upholstered jungle gym in the center of the room to great effect, but the thrill is gone so I make it an early night after all, as I squeeze pass them trying not to bump anything.

The following morning begins with Chef Dan finally getting a taker--not me--on his gluten-free pancake and both Kennedy and I dashing off early to rent jet skis from Hydro-Thunder of Key West (601 Front Street, 305-292-3388). Kennedy opts for just zipping around the bay for 45 minutes before she has to leave for the airport, but since I'm on a night flight home and slightly less Mariah Carey-ish than her, I choose the hour and a half guided tour that logs 27 miles circling Key West.

The tour lead, Tommy, introduces himself by saying, "I'm from Connecticut," in one of the thickest Israeli accents I've ever heard while his number two, Manny, looks like Cuba's answer to Pauly D. Whenever there's a break in the chain of a dozen throttled-out Yamaha 4-stroke Waverunners, these two lapse into a well-rehearsed shtick that reaches the complexity of a Lewis/Martin routine.
Still craving more ocean time before departure, I enlist for a two-reef snorkeling trip from Fury Water Adventures (2 Duval Street, 800-994-8898). Before we board the catamaran shuttling us seven miles offshore to the only living coral reef in North America, J, B., our captain, informs us we'll still be going out for two hours, but due to inclement weather, our trip will only make one stop on the barrier reef. He climbs to the catamaran's helm, points us in the direction of the lighthouse and promptly puts his feet up on the wheel and falls asleep. Down below, Monty from Lincoln, Nebraska, and Dan from South Africa give a quick tutorial on fins and masks.

Once into the drink, I can see the choppy water makes for poor visibility below as the reef's sediment is kicked up and makes floating on the surface nauseating, like bobbing for apples, only you're the apple. Nausea is quickly trumped by the first of the reef's 500 species that slowly swims into view. It's a shark, and before I even realize it's happening, I swim towards it.

I know nurse sharks are fairly common and quite harmless on the reef, but I'm close enough now to see this one is considerably larger and not swimming along the bottom as those reef sharks do. As if my mind is broadcasting with a seven-second delay, the phrase "it's a shark" repeats in my head, this time deafening.

I try to swim backwards--a very difficult task in snorkeling fins under the best of circumstances--and begin to panic. I lose sight of the shark. Now I'm really scared. I break the surface, just waiting for loss of limb. Finally, that stuttering "sh-sh-sh-shark" girl from Jaws pops into my head and I start to laugh.

I realize I'm having my second transcendental Key West moment and wonder if I stay on, could I begin to stretch them out tantrically, like orgasms? I consider it briefly, and then realize that's probably how Jimmy Buffet happened. I moderate a quick internal debate about whether informing the crew of my shark sighting will cause the trip to be canceled entirely, then decide 'fuck it' and angle my mask back down toward the breathing reef.


Tony Phillips covers the arts for The Village Voice, Frontiers and The Advocate. He’s also the proud parent of a new website:


  • , 2011-12-30 13:23:41

    Nice! Makes me want to go back to Key West again, if only to say it has "changed" (from the 60s!) Thanks Tony.

  • , 2012-01-01 17:15:17

    I have heart attacks all the time with people leaping from my moving trains. It is why I look far older than my 16 years.

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