Event Schedule
All event times are subject to change. Keep checking back here and our socials for more updates.
All events hosted at hotels are open to everyone with KWBW passes whether you're staying at that hotel or not.
​KWBW All Access Passes are the best value. All events, discounts and amenities come to over $500 if purchased individually or not discounted.
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Wristbands are available for purchase or pickup during scheduled collection times.. If you need to arrange a special pickup time please email tickets@grayjonesmedia.com
Wed Oct 29th
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12pm to 6pm – Wristband Collection
Island House, 1129 Fleming St.
Our volunteers are ready and waiting to welcome you to Key West Bear Weekend with your wristband!
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12pm to 5pm – Bear Soup Pool Party
Island House, 1129 Fleming St.
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.
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5pm to 8pm – Extended Happy Hour
Island House, 1129 Fleming St.
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.
Included with KWBW weekend pass or $50 for Island House day pass. ​ ​
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8.30pm to 10.30pm - Dive-In Movie
Island House, 1129 Fleming St.
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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. Included with KWBW weekend pass or $50 for Island House day pass. ​ ​​​
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Thurs Oct 30th
12pm to 6pm – Wristband Collection
Island House, 1129 Fleming St.
Our volunteers are ready and waiting to welcome you to Key West Bear Weekend with your wristband!
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11am to 1pm - Welcome to Key West Rum Crawl
Starting at Island House lobby
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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, 1129 Fleming St.
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! Included with KWBW weekend pass or $50 for Island House day pass.
5pm to 6.30pm – Island House Happy Hour
Island House, 1129 Fleming St.
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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! Included with KWBW weekend pass or $50 for Island House day pass.
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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!
Included with KWBW weekend pass or $15 cover
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Fri Oct 31st
12pm to 5pm - Bear Soup Pool Party
Island House, 1129 Fleming St
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! Included with KWBW weekend pass or $50 for Island House day pass.
​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! Included with KWBW weekend pass or $10 cover.
Sat Nov 1st
11am to 1pm - Leather Master Shopping Experience
The Leather Master, 418 Appelrouth Lane
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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 1129 Fleming St.
Recover and recharge ready for the evening with this pool party with chill vibes and chilled cocktails! Included with KWBW weekend pass or $50 for Island House day pass.
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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 center 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!
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Queer Keys is an LGBTQ+ community organization based in Key West, Florida. Their mission is to support, educate, empower, and celebrate the queer community in the Florida Keys.
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$20 cover (includes $5 donation to Queer Keys), included with KWBW weekend pass ($5 from every wristband sale will be donated to Queer Keys).
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Please note: as this is a charity fundraiser in aid of Queer Keys that supports the full LGBTQ+ community, all genders will be welcome at this event.
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Sun Nov 2nd
12pm to 4pm – Island House Tea Party
Island House, 1129 Fleming St.
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.
Included with KWBW weekend pass or $50 for Island House day pass.
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5pm to late – Farewell Party
Island House, 1129 Fleming St
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.
Included with KWBW weekend pass or $50 for Island House day pass.
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Alongside the scheduled activities, make the most of your time around Key West by exploring the restaurants, shops and galleries. The Key West Bear Weekend wristband will provide a range of discounts and exclusive deals (more info to follow). Also, don’t forget to use the Duval Loop free shuttle service - more info here.
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