key-west-gay-guide

Gay Guide to Key West

Key West may be a hedonistic island paradise known for its sunsets and laid-back "bohemian" lifestyle, but what truly makes it special is its large gay community. In fact, Tennessee Williams' visit in 1941 created a trend for several other artists and writers, many of whom were gay, to extend vacations on the island. Now, you'll be hard-pressed to enter a restaurant, bar or hotel without interacting with a gay staff member, and several gay-operated hotels and businesses have put the island on the map as a top gay-friendly destination.

Where to Stay

Alexander's Guesthouse
Just a few blocks from the famous Duval Street, the gay-owned Alexander’s Guesthouse is a historic, restored mansion surrounded by lush, tropical gardens. The swimming pool becomes a gay-friendly scene with happy hour cocktails, and the well-appointed guestrooms are comfortably chic with room rates that don’t break the bank.

Equator Resort
This popular resort exclusively for men is in the heart of the “gay” district on historic Fleming Street. Most visitors prefer to unwind to the fullest -- which includes hanging out at the clothing-optional pool deck. For guests requiring amped-up amenities to woo their lovers, several rooms are equipped with cool features like wet bars, high cathedral ceilings and 2-man whirlpool bathtubs that bring on the romance.

Island House
The awards keep racking up at Island House. With high marks from Travel Channel UK and Passport Magazine, this male-only, clothing-optional resort has been revered as the best gay resort in the world, and with good reason. With an ideal location in historic Old Town Key West, guests enjoy poolside dining 24 hours a day, full bar, a gym, sauna, pool, Jacuzzis and sundecks accompanied by a friendly and capable all-male staff. Best of all, many amenities are included in the rate, including afternoon happy hour, 800 calls, Wi-Fi, coffee, tea and parking.

Hyatt Key West
More “family-friendly,” Hyatt Key West is still a favorite for the gay community, thanks to its cozy rooms, myriad amenities and stellar staff. The recently renovated hotel offers great views of the Gulf of Mexico and Key West’s sunsets. Its highly touted Jala Spa is among the top resort spas on the island with a popular Cuban Coffee Body Glow signature treatment.

Things to Do

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Blu Q
Captain Steve and his crew have been offering gay water adventures for more than 16 years. Snorkel, kayak and relax on the boat or a tropical island/sandbar in the middle of the ocean. Lunch and beverages are served during each trip, and sunset trips are also offered for those memorable moments. It’s one of the best excursions on the island!

The Moped Hospital
Want to truly feel like a local? Rent a bike. Established in 1979, the Moped Hospital is the oldest scooter and bicycle rental company in Key West. Their rates are competitive, and they offer some of the newest equipment of any of the local operators. They are located 2 blocks from Duval Street on the corner of Truman Avenue and Simonton Street.

La Te Da
Iconic in Key West for its tea dance parties, La Te Da Hotel has been a meeting spot for more than 30 years. The “By George” piano bar has nightly entertainment, the Crystal Bar showcases Vegas-style illusionists Christopher Peterson and Randy Roberts, and the staff knows locals by name. But it’s the notorious Sunday Tea Dance that has locals and visitors mingling, dancing and socializing, starting at 4 p.m. So, theoretically, you can get to bed at a reasonable hour (or not!).

Where to Eat

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Nine One Five
A favorite for both locals and visitors alike, Nine One Five (located at 915 Duval in a historic Victorian house) offers fine dining (in a typical Key West casual atmosphere, of course) with Mediterranean-New American cuisine. Portions exceed expectations and chef Stuart Kemp has been twice invited to serve his cuisine for the members of New York’s prestigious James Beard Foundation. On a budget but still want to get your hands on the divine dishes? Specially priced appetizers are available during happy hour.

Louie's Backyard
Since 1971, Louie’s Backyard has offered oceanfront dining and a Caribbean-American menu for those who want fresh seafood and cool cocktails. Chef Doug Shook’s cuisine brings international culinary influences into terrific dishes, served on the restaurant’s multilevel oceanfront deck. Expect everything from fresh Key West pink shrimp to chorizo-stuffed Berkshire pork.

Harpoon Harry's
Harpoon Harry’s is a true 1950s diner located across the Historic Seaport on Caroline Street, and owners Robert and Ron will greet you with a “Bloody Harry.” In their diner you can try fish tacos, blue-plate specials and half-pound burgers. Dining here is quite the experience: The restaurant gets packed with local fishermen, politicians and pundits, and drag queens and tourists.

Key West After Dark

Bourbon Street Pub
Located on Duval Street, Key West’s most popular (and perhaps “diviest”) gay club showcases music videos, male dancers and pool parties, in addition to a Jacuzzi, a café and sundecks in the garden bar.

Aqua Nightclub  
With a weekly lineup of fun dance parties, Aqua feels more Miami (it’s the most “contemporary” bar) with a popular “Reality is a Drag” female impersonator show. Additionally, Mondays bring the ever-popular “Dueling Bartenders” where 2 bartenders in drag entertain guests with their vocal renditions of popular songs.

Bobby's Monkey Bar
Best bar name in Key West goes to Bobby’s Monkey Bar. This popular watering hole offers reasonably priced libations, with fun recreation to boot like pool, karaoke and free Wii.

About the Author

Jimmy Im is NYC-based travel writer, TV host and instructor, as well as the cofounder of OutEscapes.com. As an avid traveler, Jimmy has trekked the globe for exciting adventures, from taking a cargo vessel to the Marquesa Islands to bullfighting in Spain (seriously!). If he's not discovering new territory, Jimmy can be found in the comfort of his Lower East Side neighborhood.