Every Saturday at midnight, at Bourbon St. Pub, 724 Duval. Win $50 cash / $50 bar tab. Also - every night at Bourbon Street, 10pm: the Men of Bourbon, Key Wes't Hottest Male Dancers - "no one has more beef on the reef!" Pool and multiple clothing-optional sun decks, play areas.
February 25-26, 2017, 10am-5pm. Annual 2-day juried outdoor fine art festival, over 100 artists. Watercolors, oil & acrylic, sculpture, & photography - along Whitehead Street from Greene to Eaton, & on Caroline Street through the Presidential Gates to Truman Annex.
March 2017, LGBT students and their friends flock to the beaches and the clubs of this beautiful tropical island. Take a break for spring break in a place that embraces individuality, diversity, and openness, all year long. Clothing optional pool parties, multiple sundecks and Jacuzzi, male dancers and live VJs nightly at Bourbon Street Pu/ New Orleans House.
April, 2016, Annual Drag Race at the 700 block of Duval Street. Test run, qualifying races, finals. All contestants must be in heels and look somewhat like a woman. Plus, one week later, April 30th Bed Race. 2pm race up Duval from Fleming to Petronia. 3pm Parade of Beds down Duval St. 3:30pm Racesing begins with teams of four runners and one rider.
May, 2017. Activities around town include: campfires on the beach, Play on the Water Day kayaking, paddle boarding, jet skiing, parasailing and snorkeling; daily workouts, games, bar socials, tours, sunset cruises, women-only charter cruises, tours, karaoke, Sunday Tea-Dance at La Te Da and more. See details:
June 7-11, 2017. A festival of several days of events around town, pool & dance parties, street fair, sunset sails, comedy, film, drag shows, late night clothing-optional parties, bike tours culminating with the parade on Duval Sreet.
July 5-9, 2017. Hundreds of gay naturists, guys who like to get naked at clothing-optional gay guesthouses: Island House, La-Te-Da, New Orleans House, and Equator Resort. Dance/ pool parties; Party In The Flesh; Naked Ocean Commotion; Mr Naked Key West; Black Ball Leather Party; Sunset Sail and SUP; playful Happy Ending parties, beer busts, boat adventures. Next date: Nov 30-Dec 3, 2017
August 10-13, 2017 (TBC). Key West's hottest event for men: 4 days, all-male adult-oriented theme parties, entertainment, games, cruises, tours, aquatic activities, bar socials, pool parties, Toga Party, fetish party, naked events, drag shows, male strippers, karaoke, Tea-Dance and after party, and men from around the globe. See their website for schedule + more information.
Late October, 2017. Annual 10-day adult-theme party; wild extravaganza of parades + fun-loving costumed revelers from around the globe. Each October Fantasy Fest adopts a theme to help inspire the costumes and the parade floats. Clothing-optional rooftop bar; Coronation Ball, festivals, burlesque shows, Tighty Whitey Party, pig roast, and more. Gayest event: HEADDRESS BALL.
September 6-10, 2017 (TBC). Past year at Silver Palms Inn. Annual events, the southernmost party for lesbians and friends. Raucous clothing-optional pool parties, dance club night celebrating all things female, women-only water excursions, comedy from some of brightest funny women in the industry.
Late October, 2017. Key West Business Guild’s annual fundraising extravaganza, waterside at the Truman Waterfront…at the end of Southard Street. The famous elaborate headdress competition with “over the top” entertainment, Fantasy Fest’s premier gay and lesbian event, held rain or shine. Book your tables early as this event always sells out.
Mid-November, 2017, 5-day festival screens at Tropic Cinema, 416 Eaton St, and the San Carlos Institute, 516 Duval St. Showcasing films that exhibit excellence in storytelling and capture the essence of what Key West is all about.
November 30 - December 3, 2017. Hundreds of gay naturists, guys who like to get naked at clothing-optional gay guesthouses: Island House, La-Te-Da, New Orleans House and Equator Resort. Dance/pool parties; Party In The Flesh; Naked Ocean Commotion; Mr Naked Key West; Black Ball Leather Party; Sunset Sail and SUP; playful Happy Ending parties, beer busts, boat adventures. Next: July 2018.