Get To Know The Radical Spirit Of Homosexual Key West That Retains Calling LGBTQ+ Vacationers

Key West attracts gay travelers with its offbeat, independent spirit. Photo by Mike Freas/Florida Keys News Bureau
The demand for LGBTQ+ travelers has never been higher. As global acceptance of the LGBTQ+ community continues to rise, more and more popular destinations are courting queer tourists. However, it takes much more than a coat of rainbow paint to make a gay destination.
When deciding where to spend your dollars on your next gaycation, find a locale with some real queer credentials. While many vacation spots boast “LGBTQ+-friendly” accommodations and experiences, Key West delivers a tropical paradise with gay culture baked into its DNA.
You can trace the island’s welcoming, independent spirit throughout its history. Cuban cigar rollers, pirates and marijuana smugglers are among the early influences on Key West’s revolutionary culture. The remote location — the Southernmost point in the United States — and idyllic climate continued to attract artists, writers, free-thinkers and queer people through today, where the island proudly declares it’s “Close to Perfect, Far from Normal.”
At its peak, Key West’s fiercely weird streak led to a short-lived cessation from the Union, leading to the formation of the Conch Republic. To this day, Key West prides itself on its offbeat nature, a place for those who gleefully live life on the fringe to come party in paradise.
Luminaries like Ernest Hemingway, Judy Bloom and Leonard Bernstein were drawn to the island, along with a long list of queer artists who made Key West their home or regular vacation destination. Tony Award-winning playwright Terrence McNally and Broadway’s Jerry Herman owned homes. Queer, Pulitzer Prize-winning poets James Merill and Elizabeth Bishop also spent time living on the island.
James Kirkwood, Key West resident and Pulitzer Prize-winning playwright of “A Chorus Line,” reportedly once described Key West as “a place for lost people who are a little tilted.”
That includes legendary gay playwright Tennessee Williams, who owned a house and completed several works on the island. Key West visitors can take a deeper dive into Williams’ time in Key West at the Tennessee Williams Museum — a an easily-digestible, self-guided collection of memorabilia.
With so many creatives drawn to the island, Key West’s politics and policy are much more progressive than one typically associates with Florida. Key West has been at the forefront of inclusivity, extending anti-discrimination law to transgender individuals all the way back in 2003. Key West’s Richard Heyman became the United States’ first openly-gay mayor in 1983. The island’s current mayor, Teri Johnston, is the first openly-gay woman elected mayor in Florida.
Key West’s embrace of the LGBTQ+ community is easy to see even with the naked eye. The Key West AIDS Memorial is believed to be one of the first of its kind, honoring more than 1,200 people who died of complications due to AIDS. It sits at the entrance of the Edward B. Knight Pier overlooking the Atlantic Ocean and commemorates in Zimbabwean marble the names of those lost.
Even the sidewalks are in on the action. There are four permanent rainbow crosswalks lining the intersection of Duval and Petronia Streets — right in the thick of the city’s gay entertainment district. There you’ll find hotspots like Bourbon Street Bar and Saloon One, as well as drag spots Aqua, 801 Bourbon Bar and, the home of the island’s resident celebrity impersonators Randy Roberts and Christopher Peterson, LaTeDa.
Sushi rings in New Year Key West style — in a giant replica of a women’s red high heel. (Andy Newman/Florida Keys News Bureau/HO)
Lots of places claim a gayborhood flush with nightclubs and drag bars, but Key West drag has the attention of the globe. Instead of dropping a ball on New Year’s Eve, the Key West tradition is to lower an enormous red high-heel shoe with the island’s most famous drag queen, Sushi, inside. The annual event has been broadcast as part of CNN’s yearly coverage of celebrations around the world.
That’s not the only way Key West likes to party. Womenfest has been celebrating lesbians, trans women and allies for more than 20 years. While not exclusively an LGBTQ+ event, Fantasy Fest is famously the island’s wildest event, where all types of folks shed their inhibitions (and everyday clothing). Key West’s annual Pride celebration is a legendary party that even earned a spot in the Guinness book of records for showcasing a 1.25 mile rainbow banner, created by the original Pride flag designer Gilbert Baker.
The 1.25 mile rainbow banner, created by Pride flag designer Gilbert Baker, on display in 2003. (Photo by Andy Newman/Florida Keys News Bureau.)
Of course, it’s no surprise the tropical climate and welcoming atmosphere convinces a lot of gay travelers to stay full-time. Some of the island’s most beloved and unique attractions are gay-owned and operated businesses, like the must-see Butterfly and Nature Conservatory. Gay business owners in Key West span industries, including the world-renowned culinary scene. Take Azur, a Mediterranean-inspired spot and one of our favorite brunches on the island.
Gay travelers at one of Key West’s guest houses, Island House.
The thriving LGBTQ+ community has created some uniquely Key West experiences. The popularity of the clothing-optional culture in Key West makes it possible for three guest houses on the island to offer all-male, clothing-optional properties. There’s New Orleans House overlooking Duval Street, as well as Equator Resort and Island House in Old Town. Alexander’s Guest House — which is open to all genders, and caters specifically to the LGBTQ+ community and allies — has the option to go au naturale on the sundeck.
Exclusively queer (and clothing-optional) experiences aren’t limited to dry land. The BluQ offers all-male, clothing-optional snorkeling and sand bar trips, as well as LGBTQ+ adults-only sunset sails open to all genders.
There are so many LGBTQ+ businesses and experiences in Key West, it can be overwhelming. Check back through our previous coverage for more information, or reach out to the Key West Business Guild, which has been promoting LGBTQ+ travel and businesses on the island since 1978.
Whether you end up in Key West for short time or a lifetime, it’ll certainly be a gay ol’ time.

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