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.
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.
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 5-8, 2015, 8pm, at Key West Theater (formerly Eaton St. Theater) 522 Eaton St.. Called "the funniest play of the 20th century." What happens when a divorced couple - each on a honeymoon with a new spouse - find themselves in adjacent suites and realize they still have feelings for each other?
March 17, 2015 at Bourbon Street Complex. Special St Paddy's Day Show with Jessica Grabbit at 8pm. Men of Bourbon, VJ/DJ Neil No clothing allowed in Garden Bar, dancing to the high-energy beats of DJ Neil, pool, Jacuzzi and play areas.
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. Clothing optional pool parties, multiple sundecks and Jacuzzi, male dancers and live VJs nightly at Bourbon Street Pu/ New Orleans House.
April 18, 2015, 2pm 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. April 24, 205 Bed Race. 2pm race up Duval from Fleming to Petronia. 3pm Parade of Beds down Duval St. 3:30pm the race begins. Teams of four runners and one rider.
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.
November 18 – 22, 2015, 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.
Late November, 2015. 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.