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.
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. See more weekly events at:
January 16 - February 1, 2020, 8pm. Two legendary figures of the American Theatre, Tennessee Williams and actress Laurette Taylor, meet backstage before the Chicago opening night of The Glass Menagerie, to exchange best wishes. An unopened bottle of scotch is discovered in her dressing room, and the sparks fly as they are each challenged to face down their common demon.
February 2, 2020, 6-10pm. With 6:30pm Kick-Off and a FREE SHOT EACH TIME YOUR TEAM SCORES!
Drinks Specials + Munchies.
February 15, 2020, 10am-4pm Pool Party - Everyone Welcome. Pool & Jacuzzi - DJ + sexy dancers.
February 20-25, 2020 Mardi Gras THU 8pm Queen of Mardi Gras Pageant at 801 Cabaret. FRI 5-8pm Tea Dance For All. FRI 10pm Masked Underwear Foam Party - Men Only at NOH. SAT 12-5pm Pool Party + 10pm King of Mardi Gras Contest at Bourbon St Pub. MON 12-5pm Lundi Gras Nude Pool Party at NOH. TUE 5pm Party + Pub Crawl; DJs Gary Nolan, Kyd, Rude Girl, Vogue. Shows: Jeff Moss + Bria Ansara.
February 22-23, 2020, 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 5-28, 2020, 8pm. Heartwarming, uplifting adventure of three friends, Tick, Bernadette and Adam, searching for love and friendship, who end up finding more than they ever dreamed of. With hit parade of dance favorites including It’s Raining Men, I Will Survive, Hot Stuff, Boogie Wonderland, Go West, Girls Just Wanna Have Fun, and I Love The Nightlife.
Mid-April, 2020, 2-5pm. Annual Drag Races 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, on the Saturday one week later, April 27th Bed Races - 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.
April 17-26, 2020. Activities range from wacky bed races to a lighthearted sea battle featuring tall ships, the Conch Republic's 36th 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."
June 3-7, 2020. 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. SAT June 9th, 10am Street Fair. SUN 5pm Parade on Duval Street.
Early June, 2020, 8-10pm. 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.
July 8-12, 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: Dec 3rd-6th.
August 12-16, 2020. 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 2-6, 2020. 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 16-25, 2020 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.
October 22, 2020. 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.
October 30 - November 3, 2019. THU 11am-6:30pm Pool Party/ Greet the Meat -Island House. 9pm Bear World Monster Ball -Bourbon Street. FRI 12-5pm Island House Pool Party. 3pm VIP Cocktails -Alexanders GH. 9pm Mr Key West Bear Contest/ Party -Bourbon Street. SAT 1pm Kingdom of Neptune Pool Party -Equator Resort. 9pm Furball -Sidebar. SUN 12-8pm Bear Ass Tea Party/ Farewell -Island House.
Late November, 2020, 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.