October 18-27, 2013. The biggest event in the Florida Keys fall social lineup. Annual week-long series of events include: The Coronation Ball crownings of the king and queen; Captain Morgan parade of 70,000 costumed revelers past the LGBT venues on Duval Street on Saturday, October 26 and mile-long street party the night before.
October 23, 2013, Headdress competition, lasciviously extravagant show, lots of sexy Key West razzle dazzle, spectacular and decadent emcees.
November 13-17, 2013, 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 29 – December 1, 2013. 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.
November 30, 2013, 10am-9pm, at The Custom House. Block party with The Audubon House, Key West Art Center, Native Colors and the Westin Resort & Marina events throughout the day: silent auction, Fringe Theater, painting demonstrations, sunset events, The Love Lane Gang, Ben Harrison and special musical guests by the Smokin’ Tuna Saloon!
December 1, 2013 - April 30, 2014, 9:30am to 4:30pm daily, at the Custom House Museum, 281 Front St. Chiefly known as a playwright, Tennessee Williams also had an artistic flair for painting. To mark the 30-year anniversary of his death, the Custom House is exhibiting a number of Williams' paintings, revealing a different facet of his life and talents.
December 4-14, 2013 at Studios of Key West, 600 White St, COCK by Mike Bartlett - brilliant/ blackly hilarious look at love, betrayal, and our desire to control/ possess that which we love. Feb 20: A DELICATE BALANCE - sharp, witty examination of limits of our responsibility to family and friends and difficulty of holding everything together. Apr 25-27: CONCH REPUBLIC (The Musical!).
December 5-8, 2013, 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 summer: July 9-13, 2014.
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.
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.