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

Thursday, October 29, 2026
Key West Bear Weekend's clothing-optional catamaran sail on Blu Q, four hours on the water with BYO drinks. It's booked directly with Blu Q, first come, first served.
Have feedback on this description? Let us knowDrag brunches, circuit nights & every party worth knowing in Key West — in your inbox every week.
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.