10 Key West Events Worth Planning Your Next Trip Around


Bear Weekend / Photo courtesy Island House

There’s no bad time to visit Key West, a haven for LGBTQ travelers looking to embrace the island’s mantra of “Close to perfect, far from normal.” The “come as you are” attitude make it an ideal getaway for great food, idyllic weather and top-notch rest and relaxation all year-around.

The unique atmosphere also makes it home for a calendar crammed with creative, crowd-pleasing events. Take a look at our round-up of ten favorite Key West events, and get ready to book your ticket.

Key West Songwriters Festival
As Madonna once said: “Music makes the people come together.” There are few opportunities to rub elbows with locals and visitors (gay, straight and otherwise) than the annual Key West Songwriters Festival. Presented and curated by BMI, the festival is the largest of its kind in the world, featuring performances at boats, bars, beaches, theaters and resorts, many of which are free. This year’s festival takes place May 8-12.

Photo by Mike Freas/Florida Keys News Bureau

Key West Pride
Get an early jump on this year’s LGBTQ Pride Month celebrations with a tropical getaway at Key West Pride June 5-9. 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). 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.

Mystery Fest Key West
Key West has long attracted literary greats like Tennessee Williams, Ernest Hemingway and Judy Blume. 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. This year’s festival takes place June 28-30 at the Studios of Key West.

Bone Island Bare It All
The clothing-optional culture of Key West is one of the island’s many draws. 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. 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. 5-8.

Hemingway Days / Photo by Andy Newman/Florida Keys News Bureau/HO

Hemingway Days
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. 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.

Tropical Heat
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 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.

Fantasy Fest / Photo by Rob O’Neal/Florida Keys News Bureau/HO

Fantasy Fest
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. The majority of the events are adult-oriented and costumed, including Fogarty’s Red Party, Tutu Tuesday and the Fantasy Fest Parade. 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.

Key West Bear Weekend
Despite tropical temps, fur is still in style in Key West for this celebration of hirsute men. Running from Oct. 30 – Nov. 3, you’ll find all the requisite foam and pool parties at Key West Bear Week, plus unique events like the Scruff Furball, Mr. Key West Bear Contest and Butch Queen Bar Crawl.

Bight Before Christmas
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. 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.

Sushi / Andy Newman/Florida Keys News Bureau/HO

New Year’s Eve Shoe Drop
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. To ring in 2020, gather at Bourbon Street Pub to see beloved drag queen Sushi get lowered in a giant red, sparkly heel.

Published at Thu, 07 Feb 2019 17:30:11 +0000