February 22-23, 2014, 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 2014, 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 11-15, 2014. 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.
June-September 2014. Will Fernandez, one of Key West’s most enchanting artists, paints and sculpts almost entirely from memory, creating humorous and whimsical works. The exhibition will display a number of impressionistic-style paintings, plus a selection of his distinctive stone, wood, and clay sculptures.
July 9-13, 2014, hundreds of gay naturists & guys who like to get naked, let it all hang out at clothing optional gay guesthouses. Dance parties, foam parties, pool parties, naked shopping and playful 'Happy Ending ' parties. Check website for more info & schedules. Next winter: December 4-7, 2014.
August 14-17, 2014. 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 4-7, 2014 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.
October 17-26, 2014, includes: INDECENT EXPOSURE clothing-optional rooftop bar; Haunting of Fort Taylor; BAHAMA VILLAGE GOOMBAY FESTIVAL; ROYAL CORONATION BALL; ADVENTURES IN BURLESQUE-LAND; HEROES AND VILLAINS 5K RUN/WALK; WOMANKIND'S BRAZAAR; SUNSET LUAU/ PIG ROAST; MEN OF LABARE TIGHTY WHITEY PARTY; ANYTHING BUT CLOTHES PARTY; FANTASY FEST PARADE; DUVAL STREET PROMENADE + more....
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.
Late-December - the 2014/15 season kicks off with the December/January production of The Price by Arthur Miller directed by Murphy Davis, followed by Private Lives by Noel Coward, directed by Rebecca Tomlinson. The third production is Orson’s Shadow by Austin Pendleton directed by Resident Director Dennis Zacek.