Every night 10pm atop the bar at Bourbon St. Pub, 724 Duval. The hottest men and boys come from all over the world to perform. Many come to the island for a vacation and while here make extra money! Private lap dances available, for up close/ personal moments. Occasional porn stars' special shows. Pool and clothing-optional sun decks + play areas. Suspended during Covid-19 emergency.
Every Tuesday at midnight. Bria sings live 8-10pm. Men of Bourbon at 10pm. Drinks specials from 8pm. Every Friday Night 5-8pm Bourbon Tea w/ Tea Dance Anthems by DJ Rude Girl. Events suspended during Covid-19 emergency. See updates at:
October 14, 2020. Save the date - see details TBA.
November 7, 2020, 7-10pm. Annual variety show presenting local Key West Artists in the professional and friendly environment of the Key West Theater. Featuring the best (and sometimes the worst) of the local performing arts community. Emceed and directed by Rick Dery.
November 27 - December 6, 2020. Wacky bed races to a lighthearted sea battle featuring tall ships, the Conch Republic's 38th Annual 10-day birthday party showcases the independent and eccentric spirit that characterizes Key West and the Florida Keys. The Conch Republic stated Foreign Policy: "The Mitigation of World Tension through the Exercise of Humor."
December 3-6, 2020. Hundreds of gay naturists get naked at clothing-optional gay guesthouses: Island House, La-Te-Da, New Orleans House, Equator Resort. Dance/ pool parties; Party In The Flesh; Naked Ocean Commotion; Mr Naked Key West; Masked Ball; Black Ball Leather Party; Sunset Sail and SUP; Happy Ending parties, beer busts, boat adventures. Next dates: July 7-11, 2021 (TBC).
February 20, 2021. 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. Past year MC Tom Luna w/ Randy Roberts, Christopher Peterson, Rocky Horror cast.
June 2-6, 2021. New dates. Festival of five days around town, pool and dance parties, street fair, sunset sails, comedy, film, drag shows, late night clothing-optional parties, bike tours. Saturday 10am Street Fair. SUN 5pm Parade on Duval Street. 2020 events were cancelled.
August 11-15, 2021. Key West's hottest annual 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/ after party, and men from around the globe. See their website for schedule + more information.
September 1-5, 2021. At Silver Palms Inn, Speakeasy Inn, Alexander's Guesthouse and other establishments. 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, parties, socials, shows and comedy from some of brightest funny women in the industry.
October 22-31, 2021. 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 costumes and parade floats. Clothing-optional parties; Coronation Ball, festivals, burlesque shows, Tighty Whitey Party, pig roast, and more. Gayest events: HEADDRESS BALL + Bourbon St Pub events.
November 4-7, 2021. Past year: THU 2-7pm Wristband collection at Island House. FRI: 12-5pm Bear Soup Pool Party; 5pm Greet the Meat Happy Hour at Island House; 9pm Beers+Bears Welcome Pool Party at Bourbon Street Pub. FRI 12-5pm Bear Soup Pool Party + 3-6pm VIP cocktail party; 9pm Mr Key West Bear Contest Party at Bourbon Street. SAT 1pm Fuzzy Flamingo Pool Party + 9pm Monster Bear Ball.
Late November, 2021, 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.