Key West
The closest you’ll get to Caribbean-blue water without leaving the continental United States, Key West is a tropical paradise and a long-time queer travel destination. In fact, Key West was the first US travel destination to target the LGBTQ+ community specifically. Today it hosts more than 300,000 LGBTQ visitors annually, thanks in part to some of the iconic queer events it hosts. While there are plenty of male-only options, Key West welcomes the whole LGBTQ community with the official city motto “One Human Family.” For a truly gay stay, check out one of the gay guest houses in the historic Old Town district, and definitely spend a night, or two, bar hopping on Duval Street.
10. Alexander’s Guesthouse
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Originally built in the early 1900s and renovated in 1981, this LGBTQ-exclusive guesthouse maintains its Old Town charm on the outside with a contemporary Key West casual style on the inside. In a sea of “men only” resorts, this is one of the few stays in the gay guesthouse area that accommodate femme-identifying travelers.
11. Island House
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If you’re looking for a retreat specifically designed for gay boys, you can’t go wrong staying at this iconic Key West guest house or visiting the pool for the day. Island House is male-exclusive and clothing-optional, you won’t even need the beach with these poolside views.
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12. 801 Bourbon Bar
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A Duval Street staple, 801 Bourbon Bar is home to a number of fabulous weekly events. Come here on New Year’s Eve to experience the iconic shoe drop with local drag queen superstar Sushi.
13. 22&Co
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The LGBTQ+ bar for everyone, 22&Co is an explosion of color, glitter, and tutus. This lesbian-owned cozy spot is always packed with a fun crowd enjoying creative martinis.
14. Womenfest 2022
Thousands of women have taken over the island for more than 20 years to celebrate Womenfest, and she’s back this year, September 7-11. Gay bars and other local businesses give the women what they want with an array of events around the island, from clothing-optional pool parties to women-only sunset sails and snorkeling. And when they say women, they mean all women, lesbians, trans women, and allies alike.
15. Tropical Heat
Escape to the Keys in August for Tropical Heat! This famous five-day event is full of parties and T-dances you don’t wanna miss.
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