See our daily events listings for bars and clubs in Key West at the link below, followed by an editor's pick of events throughout the year.
November 12-16, 2014, usually 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 28-30, 2014. A 3-day, island-wide, art festival centered in downtown Key West. The best, freshest artists alongside veteran and legendary established artists in the town's many galleries. Pottery to poetry, performance art, sculpture, interactive art, and musical performances, plus wine tastings, and fine dining, complement a lively and coordinated art walk.
December 3, 2014 - March 28, 2015. The season kicks off with the December/January production of Alice’s Parlor, four short plays by Alice Gerstenberg; followed by The Price by Arthur Miller, Private Lives by Noel Coward, Orson’s Shadow by Austin Pendleton, and CONCH REPUBLIC (The Musical!). At various venues - see website for more:
December 4-7, 2014, hundreds of gay naturists + guys who like to get naked, hang out at clothing-optional gay guesthouses: Island House, La-Te-Da, New Orleans House, and Equator Resort. Dance/ pool parties; naked Ocean Commotion, Sunset Sail, and SUP; playful 'Happy Ending ' parties, Mr Naked Key West. More info at website. Next dates: July 8-12 + December 3-6, 2015.
December 6, 2014 7pm-4am, at Bourbon Street Complex. Bare it all to enjoy the naked party with Holiday Parade views from the balcony, then compete for $500 in cash and other prizes in the Mr Naked Key West contest. No clothing allowed in Garden Bar, dancing to the high-energy beats of DJ Neil, pool, Jacuzzi and play areas. All naked men are welcome to enter the competition.
December 31, 2014 at Bourbon Street. DJ Gary Nolen, the Men of Bourbon, Sushi, special guest performers, co-hosted by Austin & Derrick (A-List New York). Big street party in Duval Street, tens of thousands of party people celebrate as Sushi,in a huge red high heel shoe drops to the ground at the stroke of midnight.
January 9 – July 30, 2015 Hemingway, one of Key West’s most famous residents, devoted a great deal of time fishing the local waters aboard his vessel, Pilar. This exhibition will not only explore his fishing exploits, but also showcase antique fishing tackle utilized during the period when Hemingway was in search of his next big catch.
February 21-22, 2015, 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 - April 2015, 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.
June 10-14, 2015. 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.
August 13-16, 2015. Key West's hottest event for men: four days of all-male adult-oriented theme parties, entertainment, and men from around the globe. See their website for schedule and more information.
September 10-13, 2015 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, 2015. Annual, 10-day adult-theme party; wild extravaganza of parades and 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.
Late October, 2015. Key West Business Guild’s annual fundraising extravaganza, at the Southernmost Hotel on the Beach. The famous elaborate headdress competition with “over the top” entertainment, Fantasy Fest’s premier gay and lesbian event, held rain or shine.