One of our favorite must-visit destinations is Key West, Florida. Year-round, Key West hosts LGBTQ+ events and festivals including Pride, Womenfest, Bear Weekend, and much more.
In Key West, you can create and enjoy a choose your own adventure vacation. Relax on the beach, enjoy amazing food and wine with friends, or discover one-of-a-kind experiences day and night. Here are some of Key West’s annual events to put on your calendar.
Key West Pride – June 2025
Though you can celebrate pride with thousands of friends in nearly any major city these days, Key West Pride is truly something special. A giant rainbow flag is carried through the streets by friends and allies, bars and restaurants are slinging drinks, and special Pride events are happening all around town.
Womenfest – September 3-7, 2025
Thousands of lesbians, bisexual, queer, and trans women have been attending Womenfest for decades. And at this Key West event, ALL women are celebrated with a range of exciting activities throughout the weekend. Highlights include luncheons, drag shows, bra-less brunches, beach bashes, art and poetry exhibitions, bike tours and more.
Headdress Ball – October 23, 2025
The Headdress Ball has been a Key West tradition for over forty years. The ball is a fundraising benefit for the non-profit Key West Business Guild, a renowned LGBTQ+ business organization. The annual ball is the ultimate game of dress up. Contestants compete with extravagant headdresses for first place and a $3,000 prize. Attendees can enjoy food and drink and stellar music from local DJs.
Bear Weekend – October 29 – November 2, 2025
Bears and people who love them are welcome at Key West’s Bear Weekend which happens every fall. Pool parties, happy hours, poolside film screenings, bar crawls, and tea parties are jam packed into a fun-filled weekend. An all access pass is just $135 and offers entry to all weekend events and parties, access to the Island House Key West Resort’s guest facilities (pool, gym, hot tubs, sauna and legendary play room), and discounts at select bars and restaurants.
Key West Film Festival – November 2025
Casual moviegoers and film fanatics alike are invited to attend the annual Key West Film Festival every fall. Showcasing groundbreaking new films, future classics and more, the Key West Film Festival has something for everyone. This year’s dates are TBD, so keep an eye out.
Read more about Key West at PassportMagazine.com
