The Perfect Gay & Lesbian Getaway in Key West
Gay-friendly attractions, restaurants, nightclubs, and accommodations abound in colorful Key West.
In Key West, gay and lesbian couples will find a perfect tropical retreat.
Here are some suggestions for where and how to spend your time in quirky, progressive and friendly Key West, a secluded yet accessible island paradise that's been a favorite gay destination for decades.
The drive south through the Keys is breathtaking. The brilliant blue-green ocean is dotted with sailboats, catamarans and wave runners; it's obvious that people are out to have an exhilarating day on (and in) the balmy waters.
You will find shells, corals and other nautical items crowding the shelves at many of the local shops that line Highway 1.
Home Away from Home
Where to stay in Key West? Gay-friendly hotels, resorts and B&Bs in this town are famed for their welcoming attitude. Quite a few clothing-optional properties cater primarily to gays and lesbians, too.
Alexander’s Guesthouse, with its sprawling, tree-shaded grounds, draws a mix of male and female couples. It’s a great choice for co-ed groups of friends traveling together.
Among men's accommodations, the Equator Resort and New Orleans House (above the Bourbon St. Pub) both offer elegant rooms, dapper pool and sunning areas, and moderate rates. Men seeking a playful, racy vibe should head to the beautifully maintained Island House, with its poolside café and bar, full health club and highly professional staff.
Out on the Town
After getting settled in, set off on foot to find a late lunch – you can walk everywhere in Old Town Key West. The crew at Alexander’s recommends Pepe’s Cafe, a small bar and grill offering the catch of the day, raw oysters and a chowder that is out-of-this-world. There, you will get in on a local favorite – the Oyster Race. It's simple: patrons get a number one through five. A shucker begins to shuck five oysters while another person keeps time. The fastest time wins. Each patron with a number matching the number on the fastest shucked oyster gets to choose a key. If the key opens a locked box, the patron wins the money inside
Then, walk down Duval Street toward what the locals call the Pink Triangle. Rainbow flags are easy to spot on Duval. Many of the establishments in Key West are gay-owned or gay-friendly, and they let you know it.
If you're seeking a sophisticated "gay date" spot, try swanky Ocean Grill & Bar, a romantic place serving a melting pot of all sorts of food.
The see-and-be-seen Mangoes, with its lovely outdoor patio, draws a colorful bunch with its delicious selection of Floribbean and American foods.
The trendy eatery Seven Fish has an urbane interior – drop by for seafood-intensive bistro fare, including delicious penne pasta with mango chutney, crawfish and scallops.
For an authentic Cuban sandwich, head to 5 Brothers Grocery, on a quiet street in the historic district.
You'll find most of the town's gay bars along Duval Street. There's the pulsing Aqua nightclub, with its wild drag shows (performed by the inimitable Aquanettes) and expansive dance floor. The "Big Easy"-inspired Bourbon St. Pub is super-friendly and plays lively videos on its many TV screens. Nearby, duck into the 801 Bourbon Bar, home to the 801 girls, a drag troupe headed by Sushi, the drag queen who stars in the "red shoe drop" each New Year's Eve that has been broadcast on CNN for many years, which has a solid group of regulars.
And don't overlook the La Te Da Hotel and Restaurant, which has a poolside lounge, a classy piano bar and The Cabaret in The Crystal Room.
There is no better place to watch the sunset than at Mallory Square. It’s a romantic sight. Gay and lesbian couples stroll hand in hand alongside straight couples. Walking around, you’ll meet lots of friendly and open people. In the Keys, no one really cares if you’re gay or straight, making gay travel to Key West an enjoyable experience.
Mallory Square hosts a Sunset Celebration every evening. The square is buzzing with musicians, acrobats, mimes and unicyclists. We peruse vendors selling their wares – jewelry, artwork and hand-painted t-shirts just to name a few.
Out on the Water
Hop on the boat for an all-day, do-it-all water sports adventure on the Party Cat with Sunset Watersports. The day includes jet skiing, snorkeling, water skiing, banana boat rides, wind surfing, kayaking and more.
Professional photographers on board will capture your best moments. You can purchase the photos on CD for a nominal fee. Lunch is available, which is the perfect time to meet the friendly staff. During the last hour of the day, draft beer is free and everyone sits together and shares their fun stories.
You might think of this relaxing, fun-loving town chiefly as a place for lazing away around the pool or gathering with friends at convivial restaurants and gay nightclubs, and indeed, you'll find plenty of these diversions. But Key West has several other worthwhile pursuits to savor.
You can trace the legacy of one of America's great literary giants at the historic Ernest Hemingway Home and Museum, and one of the nation's seminal political minds at the former vacation retreat of President Harry S. Truman, the Little White House.
Along colorful Duval Street, you'll find enough clothing boutiques, art galleries and gift shops to keep you busy for a full day or more.
Of course, the town's tropical climate and clear-blue waters account for much of its popularity. A must-do for fans of flora and fauna is the Key West Butterfly & Nature Conservatory, with its glass-enclosed environment sheltering a variety of fluttering butterfly species along with more than 20 exotic bird species, plus fragrant flowers and nectar-rich plants.
The Mel Fisher Maritime Museum displays the famed treasures of shipwrecked golden galleons.
Key West is wonderful to visit any time of year, but the town truly springs to life during several gay events. Here are some to watch for:
Late February-Early April / Gay Spring Break in Key West
The town opens its doors to LGBT students and others seeking warm-weather fun in the sun. Gay-friendly beach gatherings, exciting nightlife, dance parties, jet-skiing tours and snorkeling trips will keep you busy, and a number of shops, restaurants and accommodations offer special deals.
Early June / Key West Pride Week
A community celebration featuring a street fair, pride parade, dance parties, sunset sails, music, and film. All set on a tropical island that is legendary for its laid-back vibe and it’s open and accepting atmosphere.
Late August / Tropical Heat
A long weekend of intriguingly decedent adult parties for gay men with events including clothing optional pool parties, a feisty fetish bash, an underwear “or not” parties and much more.
Early September / Womenfest in Key West
One of the nation's premier events for lesbians and their friends, this six-day fiesta includes clothing-optional pool parties, a sizzling dance club scene, a golf tournament and women-only water excursions, while film, live music and a curiously-strong comedy show offer the opportunity to enjoy paradise at a slower pace.
For more information about planning your gay getaway to Key West, visit fla-keys.com.