← Part of Fantasy Fest Key West
Part of the Gay Key West Guide — bars, events & things to do.

Friday, October 23, 2026
Bourbon St Pub's Fantasy Fest street-fair T-dance moves poolside at the men's clothing-optional pool and garden bar. Live DJs, drag queens and games run from noon into the late afternoon, with a free clothes check and towels while they last.
Have feedback on this description? Let us knowDrag brunches, circuit nights & every party worth knowing in Key West — in your inbox every week.

Thu, Oct 22
10 PM - 4 AM
Bourbon Street Pub, Key West

Sat, Oct 24
10 PM - 4 AM
Bourbon Street Pub, Key West

Thu, Oct 29
9 PM - 1 AM
Bourbon Street Pub, Key West
The jockstrap dress-code party at Key West Bear Weekend 2026.

Sat, Oct 31
8 PM - 10 PM
Bourbon Street Pub, Key West
Let people know you're going, see who else is attending, and share the event with friends.


Bears take the southernmost tip of the U.S. for a long Halloween weekend. Here's the plan.

The complete LGBTQ+ guide to Key West — gay bars, Fantasy Fest, Pride, clothing-optional resorts, beaches, and everything you need to plan your trip to the Southernmost Point.

Your guide to the best gay beaches in Florida — the top LGBTQ+ sands from Miami to Key West, what to expect at each, and where to stay nearby.

October is Pride's last big wave and gay Halloween's first — Atlanta Pride, Fantasy Fest, Women's Week, and costume parties from WeHo to New Orleans. The best gay events in October.

Fantasy Fest takes over Key West October 16–25, 2026 — ten days of costumes, parades, and parties on a two-by-four-mile island. Here's the gay guide: the Pink Triangle, the pool parties, and how to do it right.

Everything you need for Tropical Heat 2026 — Key West's all-male, adults-only summer party weekend. Pool parties, dance events, the best gay bars, and where to stay.