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

by Tony Phillips
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...)


  • Richard Frisbie, 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.

  • Anonymous, 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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