November 30, 2022

Olympia Travel

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Gay Key West Travel Guide

The LGBTQ community gravitates to any place that’s open, laid-back, and accepting – and Key West is one such place! With a massive number of events and establishments that cater to gay people, it’s been a popular gay destination for a long time, and the LGBTQ community has given back in spades.

We’ve compiled this guide to give you all the information you need to explore and enjoy Key West. From where to stay, where to go, where to eat, and all the best hotspots for fun, we’ve got you covered!

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Shutterstock / Luna Vandoorne

What’s The LGBTQ Scene Like In Key West?

Where other places have gay neighborhoods, Key West is itself a gay city. Its gay history starts in 1941 when Tennessee Williams and Leonard Bernstein first visited the island. Gay travel to Key West picked up in the 1970s, leading to the Key West Business Guild being established in 1978 to support tourism to the island.

Key West elected the US’s first openly gay mayor in 1983. It adopted the motto “One Human Family” as the city’s official philosophy in 2000, unfurled a 1.25-mile-long rainbow flag for Pride in 2003, and elected its first openly lesbian mayor in 2018.

Gay Pride Key West

Shutterstock / Chuck Wagner

LGBTQ Events In Key West

Certain days of the calendar are even more significant to the LGBTQ community. We particularly recommend coming to these events if you want a particularly celebratory atmosphere.

Key West Pride

When is Gay Pride in Key West? It’s in June. This five-day festival has been running since 1982 and now draws crowds in the tens of thousands. Activities range from rowdy to chill to fabulous. The 2022 Pride saw performances from Destiny Montgomery, the Key West Barbershop Harmony, Jim Speake, Gwen Filosa, Kevin Assam, Bria Ansara, Abigail Houff, and more.

Tropical Heat

Gay men seeking a fun time in August should come to Key West for Tropical Heat. It’s an event exclusively for men, giving them the gayest way to explore Key West. There are all sorts of events to choose from: themed parties, clothing-optional events, vodka tastings, drag shows, and so much more. It’s the perfect time to celebrate being a gay man! Whether you want to dive straight in or just watch from the sidelines, Tropical Heat has something for you.

Womanfest

It’s not just men who get to have fun in Key West. Womanfest is one of the largest lesbian gatherings in the world, and it takes place in September. Whether you want to socialize, soak up the sun, dance the night away, or just be comfortable being a woman, Womanfest has your back. All are welcome, whether you’re single, coupled up, or anything else. Take part in your choice of events: clothing-optional pool parties, roller derby, women-only drag shows, stand-up comedy, live music, and so much more. Celebrate all women at Womenfest.

Headdress Ball

This event is all about anything worn on the head. Contestants face off to win prizes based on the best-looking and most creative headdresses, ably emceed by Laurie Thibauld of Aqua Idol. Take in the massive variety of hats, bonnets, headdresses, and other headwear the contestants bring onto the runway.

Where to stay in Key West

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Where To Stay

Many hotels and resorts in Key West are gay-friendly, so you can rest assured knowing that you’ve got a wide range of choices of where to stay. The following accommodations are excellent choices for all kinds of Gay Key West vacations.

Alexander’s Guest House

This bed and breakfast right in the heart of the Old Town provides a historical ambiance while also catering specifically to the LGBTQ community. It consists of three renovated buildings with 17 rooms, all of them uniquely decorated in a variety of styles. Breakfast is served daily, and it’s near Duval Street, the heart of the Key West gay scene.

Enjoy the pool and hot tub out the back, or two clothing-optional sundecks. Poolside happy hour is from 4:30 PM to 5:30 PM.

Island House

Right in the middle of the Old Town, Island House is one of the best gay resorts in Key West. It is male-only and clothing-optional. Guests can enjoy the pool deck with 24-hour poolside dining, as well as a full bar, gym, sauna, Jacuzzis, and sundecks, all of which are attended by a friendly and capable all-male staff.

If you have a taste for the amorous, it has a 24-hour erotic video lounge. Happy hour is from 5:00 PM to 6:30 PM every day, with in-house guests receiving 3 complimentary cocktails.

Hyatt Centric Key West

The Hyatt Centric is one of the best Gay Key West hotels, with cozy rooms, many amenities, and excellent staff. Take in the excellent views of the Gulf and the sunset right from your room. Its Jala Spa is top-rated for spas on the island. Their treatments are just the thing to get your body rejuvenated to face its next day of partying.

Sloppy Joe's Bar

Daniel Korzeniewski / Shutterstock.com

Where To Eat

The food is excellent out on the southernmost island of the US, especially when it’s prepared by the Key West LGBTQ community. Try these establishments to support a gay-owned business.

Azur

This Mediterranean-style place is in the heart of the Old Town. Chefs and owners Michael Mosi and Drew Wenzel are both gay and passionate about the food they cook, blending European flavors with Key West ingredients. The dinner menu also features a good range of options. You have the option of dining on the terrace or in the dining room – wherever your whim takes you.

The Flaming Buoy

The name, the grill, and the owners are all flaming at the Flaming Buoy. Keep an eye out for owners Scot Forste and Fred Isch, who may come out to serve you your meal and tell stories of their lives. The food mixes influences from both gourmet and home cooking, letting both foodies and non-foodies enjoy the experience. Try the lobster mac ‘n cheese, or the bacon-wrapped scallops with mashed sweet potatoes.

Bagatelle

This award-winning restaurant lies right on Duval Street, near Mallory Square. Its menu combines French heritage with Southern hospitality and the characteristic flavors of the Florida Keys. It’s the best place to get brunch, with eggs prepared in all manner of ways. We recommend the lobster omelet, served with applewood smoked bacon, Swiss cheese, and key lime hollandaise.

Where To Party

The first stop for any LGBT Key West party experience is Duval Street. All the Key West gay bars are somewhere along its 1.25-mile length. Whatever your orientation or preferred vibe, you’re sure to find something for you on Duval.

801 Bourbon

No Gay Key West vacay is complete without a visit to 801 Bourbon, the largest drag house on the island. It’s been there for three decades, owned by local drag queen Sushi. Enjoy karaoke every Sunday at 4:00 PM, Bingo Sundays at 5:00 PM, matinee drag shows every Saturday at 5:00 PM, or try the 801 Cabaret upstairs, where the 801 Girls put on a show every night. It’s one of the best gay bars in Key West!

Aquaplex Key West

The Aquaplex contains several bars all under the same label, letting you enjoy cocktails, drag shows, food, and dancing all under the same roof. The main room hosts the best drag shows in town, every night at 9:00 PM. Matinee shows are at 7:00 PM from Thursdays to Sundays. Or you can try poke bowls at Poke in the Rear, a glitter martini at 22&Co, the chill atmosphere of the Back Bar, or the Side Bar for afternoon drinks and late-night dancing.

Blu Q Catamaran

This company has been offering water experiences aimed specifically at gay men for 16 years, and it’s voted the number 1 all-gay water experience in Key West. Go on clothing-optional all-male day trips, where you get to snorkel or kayak in the water. Relax on the boat or the tropical island or sandbar they’ll take you to.

La Te Da

If you want the entire Key West experience under one roof, La Te Da can do all that. It contains accommodations, a house restaurant, two bars, and a colorful patio. While you can stay at the hotel, the real attraction here is the entertainment. The piano bar has live entertainment every night, from 8:30 PM to 11:30 PM. You can also try the cabaret shows. La Te Da plays host to many top performers like Christopher Peterson and Randy Roberts. The Tea Dance, a La Te Da fixture, is every Sunday at 4:00 PM.

Aerial view of gay Key West. Florida. USA.

Shutterstock / Mia2you

Other Fun Things To Do In Key West

Even though it’s out on the edge of the United States, Key West is still a top tourist destination. Some of these attractions will add a lot of flavor to any Gay Key West vacation.

Tennessee Williams Museum

Author of A Streetcar Named Desire, Cat on a Hot Tin Roof, Vieux Carré, and many other plays, Tennessee Williams lived in Key West from the late 1940s to his death in 1983. He lived as an openly gay man with his partner, Frank Merlo, for 14 years until Merlo’s death in 1963. The museum on 513 Truman Avenue pays tribute to his legacy, hosting a large collection of Williams memorabilia.

Tropic Cinema

This theater opened up in 2004, aiming to show more than just Hollywood’s latest blockbusters. You can catch indie films, international movies, and cinematic classics. As long as you’re willing to try something off the beaten path, Tropic Cinema has something for you. Take a photo next to the Seward Johnson sculpture of Marilyn Monroe in her white dress.

Southernmost Point Buoy

This concrete buoy is anchored to the ground at the corner of South and Whitehead streets. It marks the southernmost point of the Continental USA and is a good spot for bragging rights and selfies. Take photos of the buoy itself, or soak in the surrounding view of the Straits of Florida.

Key West Wildlife Center

Right in the middle of the Sonny McCoy Indigenous Park is the Wildlife Center. It has a nature trail with two aviaries. It’s a good place to bird watch, especially during fall and spring, when birds are migrating. You’ll see a wide range of birds: raptors, shorebirds, warblers, and songbirds all stop by the park. You can also take a look at the birds that the center cares for, including some of the feral chickens of Key West.

Ernest Hemingway Home & Museum

Many people come to Key West just to be themselves, and Ernest Hemingway is one of many writers who called it home. His house is the most popular tourist attraction on the island. While at the house, he wrote Green Hills of Africa, the short stories The Snows of Kilimanjaro and The Short Happy Life of Francis Macomber, and his novel To Have And Have Not. Explore the house where he lived and play with the six-toed cats.

The Bottom Line

No matter what kind of experience you want for your Gay Key West vacation, Key West welcomes you. Partake in the events, or just soak in the culture and the atmosphere of the island. It’s all good – you’re part of Key West’s One Human Family.

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The Ultimate Guide to Gay Travel In Key West