Biggest LGBTQ+ Festivals in Key West
Key West is one of the most LGBTQ+ friendly places in the world, so it goes without saying that the island’s annual Pride events come in all shapes and sizes. If you’re looking for the best LGBTQ+ festivals in Key West, these events will have you mingling, dancing, feeling heard, and advocating for this diverse community and beyond. So don your rainbow attire and prepare to show your pride!
2nd Week of June
June is Pride Month and Key West Pride is always a party. The biggest LGBTQ+ event of the year brings the island together under the philosophy ‘One Human Family’ for a celebration to remember. Key West Pride is packed with events like drag brunches and a street fair, but the main appeal is the Pride Parade which features the mile-long Sea-to-Sea Diversity Flag.
2nd Week of August
The all-male five-day festival includes pool parties, drag shows, clothing-optional gatherings, and themed events like the superhero ‘SuperGay’ party. Tropical Heat is held when Key West is at its hottest - in August!
2nd Week of September
Lesbians, transwomen, and allies alike - Womenfest celebrates ALL women. The five-day festival offers a wide range of activities for women like sunset sails, DJ, drag, burlesque, and comedy shows, art, poetry, dancing, pool parties, and even a clothing-optional sandbar snorkel trip.
Last Week of October
The premier LGBTQ+ event of Fantasy Fest is undoubtedly the annual Headdress Ball which takes place at the Coffee Butler Amphitheater at Truman Waterfront Park. Talented headdress makers compete for a cash prize and bragging rights. Proceeds promote Key West LGBTQ+ tourism worldwide. More LGBTQ+ events at Fantasy Fest include Bowties & Birthday Suits and the Humpday Pool Party at Island House in Old Town.
1st Weekend of November
Robin Gray, Editor of Bear World Magazine, defines a “bear” within the LGBTQ+ community as someone possessing a kind, friendly, and welcoming attitude. Sure, bears can be “usually hunky, chunky types with larger chests and bellies than average,” but Gray says if you feel and act like a bear (man or woman), then you’re a bear! Bear Weekend festivities consist of pool parties, dancing, happy hour, and cocktail parties, plus the annual crowning of Mr. Key West Bear.
Experience the lively Key West vibe for yourself. The Gates Hotel is recognized by Condé Nast as one of the best hotels in Florida and offers continuous shuttle service to Old Town so you won’t have to worry about transportation. View our room options and book your next trip.