Famously located at the southernmost point in the continental United States, the sun-drenched oasis of Key West celebrates community and individuality in equal measures. A beach lover's paradise with winter weather that averages in the high 70's, the island maintains a population of around 23,000, an estimated third of whom are LGBT (including the highest self-reportage of same-sex couples in the nation and a notably strong bi community).

"One Human Family," Key West's official motto, wasn't just made for bumper stickers: it's an aspirational phrase that captures the spirit of this pansexual love-and-let-love city on an emerald green sea. And much like a well-mixed cocktail (Jimmy Buffett's "Margaritaville" was famously written here, after all), the island is a tropical blend of cultural influences, including a substantial Cuban flavor (the city is far closer to Havana than Miami) that enriches local fashion, architecture, and cuisine.

Tourism may be Key West's number one industry, but the town is known for its local color. Famous residents of this playground for the rich and eccentric have included Ernest Hemingway (whose house is KW's best-known attraction), Harry S. Truman, Tennessee Williams, and Top Gun star Kelly McGillis, who hosts the annual Kelly McGillis Classic International Women's Flag Football Championship. The fly-your-freak-flag spirit is everywhere, applicable to both visitors and natives alike. A "Do what you will" ethos reigning supreme: just ask the wild chickens that have long roamed freely up and down the streets (though not every local is a fan of these early morning crowers).

Of course, Key West is perhaps best known as a place where LGBT folks in particular can let it all hang out, and for once you can believe the hype. Queer singles, couples, and families are everywhere, enjoying attractions such as the aforementioned Hemingway House, the exquisite Butterfly and Nature Conservatory, the Aquarium, the Forest and Botanical Garden, the Gay and Lesbian Trolley Tour, the local pirate, treasure, and shipwreck museums, and every beach and water activity imaginable. There's also plenty of shopping (though some of the stores along Duval Street, downtown's main drag, tend toward the joke t-shirt and painted conch shell clientele), galleries, and four excellent community theaters. The Gay and Lesbian Community Center has information on all of the above, and a great deal more.

It's only once the glorious Florida sun sets that Key West really heats up, with a queer-oriented nightlife that runs the gamut from sing-a-long piano bars to sleazy homo strip joints. Try the La-Ti-Da cabaret, which has been a staple here for over 30 years; newcomer The Keys, a piano bar featuring a nightly open mic where you can channel your inner Kiki Dee; The Bourbon Street Pub, with two drag shows every evening (famous for being the spot where local diva Sushi is dropped from an enormous red shoe at midnight on New Year's); and Aqua, KW's best-known club. If that all sounds too staid for you, you can always try one of the island's notorious strip clubs, such as the lesbian-friendly Teasers (for women dancers) or Kwest (for the boys). Hey, they don't call it Bone Island for nothing.

Though the island, befitting a place with a temperate climate, has a ton of year-round activities, there are some yearly events that make the trip worth it all by themselves. The ten-day extravaganza Fantasyfest (the 30th celebrated on Halloween 2009) surpasses New Orleans' Mardi Gras on the basis of debauchery alone; the annual Womenfest (beginning after Labor Day) for lesbians and those who love them; the Bone Island Bare It All Weekend; Pridefest; Gay Spring Break; Tropical Heat.... Try to make it to one of these events, if only to see how the locals turn it out for a special occasion.

If you need a place to stay, there is a wide array of choices, including the Reach, a resort offering the island's only natural beach, as well as smaller hotels like The Gardens, which is pure charm and grace. But for the adventurous, why not take advantage of what makes Key West different from other vacation towns? I'm talking about the network of guesthouses (some exclusively for LGBT clientele). There are houses for every persuasion (Island House is male hedonistic, The Equator bright and fun, the sunny and spirited Pearl's Rainbow all about the ladies), but our favorite is Alexander's, which caters to both gays and lesbians and is elegant and playful in equal measures. Highly recommended.

Dining is one of Key West's main attractions, from local comfort food spots like Camille's and Harpoon Harry's, to tonier restaurants like Square One and the Strip House at the Reach. Steakhouses and seafood restaurants, brunch and Cuban joints: they're all on the menu, with a wide range of price points. You can eat cheap and delicious, or go all out and upscale (though casual dining is always the order of the day in Key West). You'd be remiss if you didn't partake in a slice of key lime pie (trust me, a little goes a long way), the best of which can be had at Kermit's. And don't pass up a conch dish in the keys if given the chance (when Key West threatened faux succession in 1982, it was subsequently dubbed "The Conch Republic)--they know from conch.

Key West has something for everyone (how many vacation towns have an equal measure of strip joints and bookstores?). So make the island is your oyster (or conch shell). And plan accordingly.