Key West, Fla., is an attitude, a watercolor, a sea chantey. It is drag queens and pirates, artists and writers, treasure hunters and happy dykes. But first and foremost, it is an island. From its earliest days its evolution has been intertwined with the sea. It was once North America's busiest port as well as the wealthiest city per capita in the United States (circa 1828-1860). Its natural deep-water harbor made it perfect for ships carrying supplies from Europe, Africa, and South America. But its coral reef, the only living reef in North America, made the passageways perilous. One man's misfortune was another's treasure as captains lost their cargo only to have it retrieved by wreckers who made their fortunes selling the salvage. Key West has always been able to change misfortune into good luck, like turning bitter key limes into delectable key lime pie or taking advantage of its remote, laid-back location to offer a tropical sanctuary to gays and lesbians.
Most people think of Key West as the end of the road, the place where U.S. 1, the Overseas Highway, after dramatically bridge-hopping from key to key, dead-ends at Mile Zero. But it's really the beginning of a beautiful stretch of water where the Atlantic Ocean and the Gulf of Mexico embrace. You can glide over these endless shades of blue, the warm wind filling your sails, the Veuve Clicquot kept chilled on a private luxury yacht charter. With options from cozy, classic wooden sloops to sleek and racy catamarans, you can easily create your own seafaring fantasy. Charters and rentals abound, and Key West is an ideal spot to easily sail away your summer without having to go deeper into the Caribbean. About 30 miles southeast of Key West, the Marquesas Keys are a classic coral atoll with a circle of low islands surrounding a protected lagoon, near where the 1622 treasure wreck of the Atocha was discovered. Snipe Point and the Mud Keys, about 10 miles north of Key West, are a series of islands and channels ideal for getting off the deck and exploring by kayak the abundant bird life of herons, egrets, ibises. And at Western Sambo, seven miles south of Key West, coral ridges create reef canyons overflowing with over 200 species of tropical fish, corals, and plants in fantastically carved caves.
Most yacht charters, whether sail or motor, include perks like Jet Skis, dive gear, gourmet picnics on deserted, unnamed beaches, or even spa treatments as your crew attends to your every need. Some even bring along sea kayaks-on a recent paddle north of Key West, I was escorted by three dolphins who found my pace a bit too leisurely, so they gave me a little push to hurry me on. They must have been unaware that "Slow down; this ain't the mainland" is a Keys mantra.
Island life keeps its own pace, albeit a bit more caffeinated than the languid days when he-man Ernest Hemingway as well as queer writers Tennessee Williams and Elizabeth Bishop hung out here. Gay writers still migrate to Key West to soak up mango sunsets and conch fritters. Don't be surprised to see Edmund White or Terrence McNally out for a bucci, a sugar-infused shot of espresso. Or check out nautical history at Captain Tony's (the original Sloppy Joe's), where queers and queens have elbowed up to the bar with sailors and Navy men for decades. In the early 1960s it was called the Olde Bar and was the first gay-friendly watering hole on the island. Of course, the main gay attractions are around Duval and Petronia streets, known as the pink triangle. Despite the gnashing of teeth over the presence of cruise ships disgorging sunburned tourists, Key West persists as a prominent gay destination, even as gay travelers nowadays have nearly unlimited options. Key West has staying power, and there remains an idyllic--and sometimes outrageous--gay community that makes its own continual party.
And party it does: Nearly every weekend, whether you want them or not, Key West has street fairs, drag shows, leather parties, women's flag football tournaments, and special events for bears, nudists, bisexuals, and everyone else. Your stay can be gloriously gay at one of the rather upscale 35-plus LGBT guesthouses in Key West, many housed in historic plantation-style buildings with sweeping porches and clothing-optional pools. Not bad for a two-by-four-mile island with a population of roughly 26,000.
Despite the changes descried by those who "knew her when," Key West has an irresistible charm that can't be condoed, concreted, or cruise-shipped to death. From the frangipani-scented air of quaint alleys to the quiet beauty of the beach at Fort Zachary Taylor-or Fort Liz Taylor, as it's known to locals-you can still find paradise here at the gay end of the glorious road.
Plan your own Key West charter
To map a private course through the waters of Key West, contact one of these gay or gay-friendly yacht/sailing companies.
Danger Charters (305-296-3272, www.dangercharters.com): Danger and Danger's Prize, both 65-foot replicas of traditional schooners, are licensed to carry up to 27 people. Call for private party pricing.
Double Decker Sailing Charters (305-731-7232, www.saildoubledecker.com): private sailing trips for up to six people on a 36-foot Cheoy Lee Sloop, ranging from sunset viewing ($70 per person) to a lobster and shrimp dinner at sea ($150 per person).
Islescapes (305-923-3319, www.islescapes.com): gourmet cruises, sunset sails, snorkeling excursions ($95/hour up to 6 guests; two-hour minimum) and extended trips are available on board a restored 33-foot motor yacht.
Skinny Dipper Cruises (305-240-0517, www.skinnydippercruises.com): gay-owned company offering private three-hour charters at $125/person (up to 6 people) on a 28-foot cabin cruiser.
Southernmost Sailing (305-766-4683, www.southernmostsailing.com): hire a crew or sail yourself; their Key West fleet includes five sizes of sailboats and catamarans ranging from $2,800 to $6,500 for a week (plus captain's fees).