One of the nation’s most famous New Year’s Eve celebrations, Key West’s annual red high-heel shoe drop is a must-see event. Sushi / Andy Newman/Florida Keys News Bureau/HO Get into the spirit with the “Harbor Walk of Lights” which features festive lights, a fishing buoy Christmas tree, nautical Christmas tree and a lobster trap Christmas tree. Lots of snowbirds flee to Key West to escape the thundersnows and bomb cyclones in Northern climates, but it’s not just the weather that makes Key West an attractive holiday getaway. Key West Bear Contest and Butch Queen Bar Crawl.
3, you’ll find all the requisite foam and pool parties at Key West Bear Week, plus unique events like the Scruff Furball, Mr. LGBTQ visitors should be sure to scoop up tickets to the popular Headdress Ball, where category is: How’s Your Head? Realness and proceeds benefit the Key West Business Guild, the nation’s oldest LGBT Chamber of Commerce.ĭespite tropical temps, fur is still in style in Key West for this celebration of hirsute men. The majority of the events are adult-oriented and costumed, including Fogarty’s Red Party, Tutu Tuesday and the Fantasy Fest Parade. Originally started in 1979 to drum up tourism during the island’s slow season, Fantasy Fest has grown to a 10-day October celebration that’s equal parts Mardi Gras, Carnival and Folsom Street Fair. Fantasy Fest / Photo by Rob O’Neal/Florida Keys News Bureau/HO
The full schedule of events for this year has not been released, but last year’s festivities included pool parties, traffic light parties, glow parties, toga parties and fetish parties.
There’s no shortage of sexy parties in Key West, but if you want to maximize your chance to party alongside tons of the hottest guys, book your trip for Tropical Heat, August 14-18. The island pays homage to Hemingway with an annual celebration featuring a look-a-like contest, marlin fishing tournament, 5K sunset run and paddleboard race, all kicking off July 18. One of Key West’s most popular attractions is Ernest Hemingway’s home, a gorgeous estate where the author lived and wrote for more than a decade.
Hemingway Days / Photo by Andy Newman/Florida Keys News Bureau/HO If you’ve been looking to explore the naturist in you (or just eager to meet other friends in the buff) this year’s Bone Island Bare It All (link NSFW) takes place July 10-14 and Dec.
Founded by Key West’s “Naked Realtor” Dean Townsend, this series of events spans some of the island’s hottest bars, guesthouses and retail spaces. The clothing-optional culture of Key West is one of the island’s many draws.
This year’s festival takes place June 28-30 at the Studios of Key West. Literary types with a passion for a good whodunit make their way to the island for the annual Mystery Fest, a weekend packed with panels, presentations and parties. Key West has long attracted literary greats like Tennessee Williams, Ernest Hemingway and Judy Blume. The event schedule is still being worked on, but last year’s celebration included film screenings, pool parties, stage readings and, of course, a parade. There are plenty of LGBTQ guesthouses and LGBTQ-friendly hotel options, and partying alongside the recently-elected first openly-lesbian mayor of a major Florida City are just a few reasons to carve out some time to celebrate with Conchs (and the people who love them). Get an early jump on this year’s LGBTQ Pride Month celebrations with a tropical getaway at Key West Pride June 5-9. Photo by Mike Freas/Florida Keys News Bureau