Key West Bear Weekend 2025 (FL)

Info

Key West Bear Weekend takes place from the 29th October to 2nd November 2025.

Wed Oct 29th
12pm to 6pm – Wristband Collection Island House. Our volunteers are ready and waiting to welcome you to Key West Bear Weekend with your wristband!
12pm to 5pm – Bear Soup Pool Party Island House, The famous Island House welcomes the bears and their admirers as you arrive in sunny Key West! Grab a swimsuit (or not!) and meet the rest of the gang with lunch poolside. The drinks are cool and the bears are hot! Included with KWBW weekend pass or $50 for Island House day pass.
5pm to 8pm – Extended Happy Hour Island House. Kick off Key West Bear Weekend with the popular Island House extended happy hour! Hotel guests receive a premium open-bar happy hour, and bears staying elsewhere enjoy 2-4-1’s on EVERYTHING! The Island House Café will be whipping up tons of FREE gourmet appetizers, passed around poolside by their fabulous naked men.
8.30pm to 10.30pm - Dive-In Movie Island House. Chill-out in or around the pool and watch a movie on the big screen with our dive-in movie concept! Movie to be announced nearer the time.

​Thurs Oct 30th
12pm to 6pm – Wristband Collection Island House. Our volunteers are ready and waiting to welcome you to Key West Bear Weekend with your wristband!
11am to 1pm - Welcome to Key West Rum Crawl Starting at Island House lobby Get into true Key West island life mode by joining us on this walking tour of Old Town Key West as we visit local rum distilleries for a taste of true Caribbean rum!
1pm to 5pm – Bear Soup Pool Party Island House. Another pool party beckons! Grab a swimsuit (or not!) and meet the rest of the gang. The drinks are cool and the bears are hot.
5pm to 6.30pm – Island House Happy Hour is a Gay Key West MUST! Hotel guests receive a premium open-bar happy hour, and bears staying elsewhere enjoy 2-4-1’s on EVERYTHING.
9pm to late - Jocktober Party Bourbon St Pub Pool Garden (at rear), 724 Duval St Strip down to your jocks and socks and dance the night away at Bourbon St Pub around their pool and garden with spot prizes for the best buns! Hosted by our special go-go guest, Ner.
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Fri Oct 31st
12pm to 5pm - Bear Soup Pool Party Island House. Another pool party beckons! Grab a swimsuit (or not!) and meet the rest of the gang. The drinks are cool and the bears are hot.
​10pm to late - Horny Halloween with Cock Shock Saloon 1, 504 Petronia St This is the HOTTEST and SPOOKIEST night of the weekend! Gear up, look scary and get down to Horny Halloween for two hours of sexy bears in spooky fetish gear as we lead into Cock Shock, a Key West institution, with their infamous contest starting at midnight... things get very raunchy with these studs.

Sat Nov 1st
11am to 1pm - Leather Master Shopping Experience The Leather Master, 418 Appelrouth Lane Check out this unique shopping experience which includes an open bar and clothing optional shopping. Leather, sex toys, hot bears, shopping and cocktails, who could ask for anything more?
2pm to 6pm – Recovery Pool Party Island House. Recover and recharge ready for the evening with this pool party with chill vibes and chilled cocktails.
10pm to late - PIrates of Men's Pants, in aid of Queer Keys Birdcage Cabaret (previously known as Side Bar), 504 Angela St Ahar me hearties! Key West has been at the centre of pirate stories for centuries, so get ready to plunder some booty at our pirate-themed party! Your host Cap'n Ner is ready to help in your search for Poppers of Eight and to ensure your Roger is properly Jollied!

​Sun Nov 2nd
12pm to 4pm – Island House Tea Party Island House. Our host hotel does what they do best on Sundays, as locals and visitors alike gather for this frisky clothing-optional shindig! Drink discounts, raffles, giveaways, drag queens, and free shots! Island House on Sundays is the place to be And attracts a big local crowd. 5pm to late – Farewell Party Island House. Chill out and relax at our farewell party. Wind down in style with a quiet pool, cool cocktails and chilled out music. Your last chance to say goodbye to friends new and old.