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!

[The Key West Drag Scene]

Key West 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.

Tropical Heat Key West

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!

[Book Direct with The Gates Hotel Key West and Save up to 25% Only When You Click Here]

Key West Womenfest

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.

Key West Headdress Ball

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.

Key West Bear Weekend

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.

[Our Favorite Gay Bars in Key West]

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.