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Key West Bear Weekend takes place from the 30th October to 3rd November 2024.
Wed 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!
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.
5pm to 8pm – Greet the Meat with Extended Happy Hour. Island House, 1129 Fleming St. Kick off Key West Bear Weekend in style with our official first night party! 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! To greet the meat, the Island House Café will be whipping up tons of FREE gourmet appetisers, passed around poolside by their fabulous naked men. Start the weekend right by meeting the rest of your furry friends in an all-male, clothing optional oasis. Included with KWBW weekend pass or $50 for Island House day pass.
Thurs Oct 31st
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!
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.
5pm to 6.30pm – Island House Happy Hour. Island House, 1129 Fleming St. 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.
9pm to late - Halloween Party. Bourbon St Pub Pool Garden (at rear), 724 Duval St. Get ready for a FRIGHTENING night of furry ghouls, goblins and other scary sights! Get your best Halloween costume together and dance the night away at Bourbon St Pub around their pool and garden, with spot prizes for the best costumes! Included with KWBW weekend pass or $15 cover
Fri Nov 1st
12pm to 5pm - BIKE Strap Pool Party. Island House, 1129 Fleming St. Sun's out, buns out! Let's see those cheeks at this jockstrap pool party, sponsored by BIKE! Expect shot boys and BIKE Swag being given away, hosted by Key West's own Puddin’ Tain. Included with KWBW weekend pass or $50 for Island House day pass.
10pm to late - Bad Bear with Cock Shock. Saloon 1, 504 Petronia St. Have you been a bad bear... Or do you want an excuse to be one?! This is the HOTTEST night of the weekend! Gear up and get down to Bad Bear for two hours of sexy bears in 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 2nd
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 1129 Fleming St. Chill out with your fellow bears poolside for food, cocktails and fun as you recharge ready to party again! Included with KWBW weekend pass or $50 for Island House day pass.
9pm to late - GLOW, in aid of Queer Keys. Side Bar, 504 Angela St. Get ready for a GLOW up as we dance the night away to hot beats raising money for Queer Keys. Wear UV, glow paint, neon and more for a truly glowing experience! Ding dong! $20 cover (includes $5 donation to Queer Keys), included with KWBW weekend pass ($5 from every wristband sale will be donated to Queer Keys). 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.
Sun Nov 3rd
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.
4pm to 6.30pm - La Te Da Tea Dance. La Te Da, 1125 Duval St. The famous La Te Da Tea Dance is a Key West tradition and features great music poolside with local radio DJs Rude Girl and Molly Blue. With expert mixologists ready to blend famous Key West cocktails and Martini specials, this is an iconic way to bring the weekend to a close. The La Te Da restaurant opens immediately after the Tea Dance too!
8pm 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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