It’s easy to get swept away by Key West’s charm. Walk down Historic Old Town roads lined with picturesque conch-style houses, and you’ll stumble upon the stomping grounds of Tennessee Williams, Elizabeth Bishop, Leonard Bernstein, just to name a few.
Key West has long been known as a place where queer people can enjoy a peaceful vacation as their authentic selves. This is why more than 300,000 LGBTQ visitors flock to the island each year. With annual events like Fantasy Fest and Womenfest, it’s not hard to see why. It has become one of the most popular destinations for the “L” in LGBTQ.
At the helm of this ship is Teri Johnston, Florida’s very first openly lesbian mayor. Teri tells GayCities that it is the “one human family spirit” that draws folks in. “We are one big accepting, diverse family,” she explains. “We argue, disagree, laugh, cajole but at the end of the day, we are there for each other, as well as any guest to our island who wants to contribute and join this big loud family. The Conch Republic lives on stronger than ever.”
Off the clock, Teri enjoys the laidback vibes this island offers. “I love to sit on my front porch on Stump Lane with my partner, two Cavalier King Charles Spaniels in my lap, and Lily cat ruling the house. R&R is on the golf course or reading at Fort Zachary Taylor State Park under the Australian Pine. Biking around Key West is a fun way to see all that our community has to offer– from our historical wood frame district to our bustling nightlife of Duval.”
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Key West’s world-famous Duval Street is the epicenter of life on the island. While Duval has a reputation for catering to a gay male crowd, the nightlife scene welcomes all. When asked where can lesbians feel most comfortable in town, Teri replies, “Anywhere and everywhere. We are a progressive community with a woman mayor and city manager and many, many incredible women heading up important organizations and nonprofits.”
On that note, here are a few of our favorite LGBTQ-friendly, female-focused spots on the island for your enjoyment.
Key West Hotspots
Alexander’s Guesthouse
Originally built in the early 1900s and renovated in 1981, this gay-owned, LGBTQ-exclusive guesthouse maintains its Old Town charm on the outside with a contemporary Key West atmosphere on the inside.
22&Co
Owned and operated by a loving lesbian couple, 22&Co is one of Key West’s most inclusive (and most glitter-filled) bars. With decor reminiscent of a fuzzy Lisa Frank poster and creative martinis to match, you’re sure to have a fun night and get some cute pics for the ‘gram. Tutus included.
“Off The Hook” Grill
This oceanside outpost lives up to its name with delicious seafood, American classics, and friendly service. A big plus, this business identifies as women-owned. A stone’s throw from Alexander’s Guesthouse, this bar and grill is a great spot for a quick bite or dinner with friends.
Tropic Cinema
More than just a movie theater, this volunteer-run cultural hub curates a selection of indie flicks and mainstream classics along with concerts, lectures, and unforgettable parties. Their one-of-a-kind, aqua-blue Art Deco marquee is like a beacon for those who long for something more than Hollywood blockbusters.
The Green Pineapple
Mix together a boutique, a wellness cafe, a yoga shala, and you’ll get The Green Pineapple. Its bustling Duval Street location offers eco-friendly apparel for all genders, one-of-a-kind gifts, and accessories. The cafe is a great place to grab plant-based, gluten-free bites, juices, and smoothies throughout the day. It also hosts a daily happy hour with a worldly selection of organic, biodynamic, and sustainable wines.
801 Bourbon Bar
Home to Sushi the Drag Queen and the 801 Girls, this happening Duval Street watering hole hosts a full calendar of events, including live entertainment, bingo, and karaoke nights. Try one of their specialty cocktails or catch a show at the 801 Cabaret above the bar, the girls perform nightly. On New Year’s Eve, this bar hosts the Key West Shoe Drop, a sight to behold.
Discover more LGBTQ-friendly places in Key West in our City Guide.
