Womenfest Key West: Where Queer Women Find Their Island Paradise

For nearly four decades, Key West has had a special September tradition: Womenfest, a celebration that turns the famously LGBTQ-friendly island into an even more concentrated gathering place for lesbians, bisexual women, queer women, trans women and their friends.

The story actually reaches back to 1986, when Walt Marlowe of the Key West Business Guild proposed a dedicated women’s week, inspired by similar lesbian gatherings in places such as Provincetown and California’s Russian River. Local women—including Jean Colton, Mary Quinn and Deborah “Stretch” Frew—helped organize the first event, called Women in Paradise. Cocktail parties, snorkeling, theater, golf and plenty of playful contests established a formula that has evolved dramatically but never lost its emphasis on women coming together.

By the 1990s, the event had developed into the Womenfest that visitors recognize today. It survived leadership changes and even periods of uncertainty about its future, eventually becoming a signature event in Key West’s LGBTQ tourism scene. By 2004, Womenfest was attracting more than 5,000 women, with performers, art events, tea dances, water excursions, and parties spread around the island.

Why lesbians should put it on the calendar

The appeal isn’t simply that there are many queer women in one tropical place—although that certainly helps. Womenfest creates something increasingly rare: a vacation environment where queer women are not a niche audience but the main event.

The program combines what Key West does best—sunset sails, snorkeling, swimming, nightlife, art, music, cocktails, and wandering Old Town—with events designed to foster connection. Singles can meet other women; couples can socialize; longtime friends can make it an annual tradition. The atmosphere is deliberately relaxed and inclusive rather than overly corporate or convention-like.

Womenfest offers something that can’t quite be replicated by a Pride weekend or a conventional beach vacation: several days when queer women can arrive in Key West and feel that the island is speaking directly to them. Come for the parties, stay for the sunsets—and you may leave with a new circle of friends, a new crush, or simply the feeling that you found your people.

Womenfest 2026

Key West Womenfest, the ultimate celebration for women in paradise, returns Wednesday, Sept. 2 through Sunday, Sept. 6, 2026, with the theme “Lost Women in the Arts” — a festival that invites women to reclaim and celebrate their creative power, individuality, and sense of belonging in the island’s legendary “One Human Family” spirit.

Here is the lineup of events:

Sept. 2 — Official Womenfest 2026 Welcome Party: Lost Women in the Arts: Kick off Womenfest at Key West’s storied American Legion Post 168 with local artists, live music, raffles, live portraits, and plenty of opportunities to connect with new and longtime friends.

Sept. 3 — 6th Annual Cornhole Tournament and Indoor Games: The iconic American Legion Post 168, once a venue for musical icons such as B.B. King, Etta James, and Otis Redding, is the place to be for an afternoon of friendly competition, games, and camaraderie.

Sept. 3 — Drag King Bootcamp: BruceKey leads this interactive workshop at Bourbon St. Pub, exploring persona creation, stage presence, and performance style. Later, participants can join professional drag kings onstage at the Green Goddess & Kings Party.

Sept. 3 — Womenfest Sunset Sail aboard Argo Navis: Hosted in partnership with the Key West Business Guild, this all-inclusive two-hour sail offers tropical breezes, sunset views, craft beverages, cocktails, and passed appetizers as guests cruise the waters where the Atlantic Ocean meets the Gulf of Mexico.

Sept. 3 — Greeen Goddess & Kings Party: Sponsored by The Greeen House and hosted by BruceKey, this high-energy celebration of drag king artistry at American Legion Post 168 features performances by acclaimed drag kings Justin Case and Joey Night, plus the debut of three Womenfest Drag King Bootcamp participants. DJ Mr. Enjoy keeps the party going all night.

Sept. 4 — Plogging the Keys Waterfront Cleanup with Reef Relief at the Key West Historic Seaport.

Sept. 4 — Clothing Optional Sandbar Snorkel Trip aboard Blu Q: Experience an exhilarating sandbar adventure where guests can enjoy sun, sea, and the company of like-minded travelers in a comfortable, inclusive setting.

Sept. 4 — All-Welcome Pool Party: Cool off, soak up the sunshine, and mingle with fellow Womenfest attendees at this annual celebration at the Bourbon St. Pub.

Sept. 4 — The Lost Women Throwdown—Jell-O Wrestling: This festival favorite brings outrageous fun, fierce competition, music, drinks, and an abundance of messy excitement. Private event for Womenfest participants.

Sept. 4 — Official Womenfest Concert: See website for details.

Sept. 4 — The Hush Hush Theater presents “Babes For Days” at Viva Argentinian Steakhouse: A femme focused cabaret show featuring burlesque, comedy, drag, song and cirque.

Sept. 5 — Lost Women, Found Art Gallery Trolley Tour: Celebrate the creativity and impact of women in the arts while visiting five women-owned and women-managed galleries throughout Key West. Meet artists and gallery owners and discover the stories behind the island’s vibrant arts community.

Sept. 5 — Making Waves: Official Womenfest Pool Party hosted by BAM with DJ Erik: Dance, swim, and soak up the island vibe at the Lighthouse Hotel during an afternoon of music, sunshine, and connection.

Sept. 5 — Annual Womenfest ’80s, 90s and Today’s Prom: “Lost Women in Music” is the theme for a sparkling tribute to groundbreaking female artists. Don your favorite 80s, 90s, or theme attire, take prom-worthy photos, and dance the night away at the historic American Legion Post 168.

Sept. 6 — Womenfest Community Worship Service: Rev. Gina Durbin hosts a Sunday service at Metropolitan Community Church centered on hope, love, and community.

Sept. 6 — “You CAN Sit With Us” Drag Brunch: Enjoy spectacular drag performances, delicious food, and nonstop laughter as some of Key West’s most talented entertainers take the stage throughout the afternoon at The Key West Cooking Show.

Sept. 6 — Hot Dog Church: Hot dogs and games offer chill Sunday fun at American Legion Post 168.

Sept. 6 — The Original Tea Dance, A Key West Tradition at La Te Da: Wrap up Womenfest 2026 with a final dance at La Te Da featuring DJ Rude Girl.

Key West Womenfest is presented in part by the Monroe County Tourist Development Council and the Key West Business Guild. For ticket links and information, including an extensive list of daily activities, visit the website.

The best Key West hotels for lesbians are here.