KWBG Signature Events

The Key West Business Guild delivers a robust LGBT tourist presence on the island every year. Our island guests are greeted with a welcoming Gay Key West Visitors Center. In 2018, the KWBG will produce THREE signature events, funded with TDC marketing dollars.  All KWBG members are welcome to participate in our events.  We encourage all members to become sponsors of the events.  Contact our office for more information.



Key West Pride – June 6-10, 2018

Celebrate PRIDE on a tropical island that is legendary for its laid-back style and its open and accepting atmosphere.  Whether you’re looking to party with friends, travel with family, or get lost in the magic of our tropical island, rediscover Key West and discover how one island’s One Human Family philosophy has created one of the most integrated and unique communities in the world.  Show us your pride, we will show you our Key West Pride!


 Tropical Heat – August 15-19, 2018

TROPICAL HEAT is Key West’s “HOTTEST” event for men!  The temperature is not the only thing that will rise during Tropical Heat.  The all-male theme parties, pool parties, and adult-oriented entertainment promises to be HOT!  August on the Island is always HOT, but during Tropical Heat it promises to be STEAMY!  Four days of hot guys and fun, the best way to experience Key West.


Key West Womenfest – September 5-9, 2018

Just before the school year starts in earnest… just as the last rays of summertime finally set… just before the holiday season begins to rev up… Key West welcomes women from across the globe to an annual celebration that has become one of the largest gatherings of lesbians and friends in North America—Womenfest! Each year thousands of ladies come together over the Labor Day weekend and stay for a wide range of activities and events during four days of revelry and fun. Key West boasts restaurants that offer remarkable cuisine year round, watering holes that offer authentic, tropical libations and shops that can’t be found anywhere else. Of course, the most popular activity during Womenfest usually involves a chaise lounge, a good book, sunscreen and a killer margarita. Come join us on our little island that is close to perfect but far from normal for this fabulous event that gets bigger and better every year!

Key West Headdress Ball – October 25, 2018

Get out your feathers, glue guns and ribbons, because it’s time for the Key West Business Guild’s annual fundraising extravaganza, the 36th Annual Headdress Ball, on Thursday evening, October 25th. The famous elaborate headdress competition with “over the top” entertainment, is Fantasy Fest’s premier gay and lesbian event. Cash prizes for categories held rain or shine.

Doors open at 7 pm. and the show begins at 8 pm.

For more information, please visit KEY WEST HEADDRESS BALL