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Key West Bear Weekend takes place from the 1st to 5th November 2023.
Wed Nov 1st
2pm to 6pm – Wristband Collection Island House, 1129 Fleming St.
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 6.30pm – 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.
Thurs Nov 2nd
12pm to 6pm – Wristband Collection Island House, 1129 Fleming St.
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 – Greet the Meat Happy 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 - ‘Bearbie’ Pink Party. Bourbon St Pub Pool Garden (at rear), 724 Duval St Are you Kenough? Put on your best pink outfit and head on down to our Bearbie Party to celebrate one of the best movies of the year! Dance the night away at Bourbon St Pub around their pool and garden with hot pink, hotter bears and cool drinks!
Fri Nov 3rd
12pm to 2pm - Key Lime Pie Crawl Starts at Island House, 1129 Fleming St. Key Lime Pie is an institution! What better way to experience this pie than by joining us on a key lime pie crawl around five of the island’s best eateries?! With a slice of pie to be consumed at each destination, you’ll not only get to know this pie very well, but you’ll also experience a SLICE of Key West on a walking tour around the Old Town. Each destination offers something different and there’s more than just pie on offer as we experience trinkets, gifts, key lime pie drinks and so much more!
2pm to 6pm – Pool Party Island House, 1129 Fleming St. Join your fellow bears poolside for food, cocktails and fun! Included with KWBW weekend pass or $50 for Island House day pass.
10pm to late - Gear Night and Cock Shock Saloon 1, 504 Petronia St. Two Key West nights come together for Key West Bear Weekend in our HOTTEST night of the weekend! First, gear up and get down to Cody & Kevin’s Gear Night, two hours of sexy bears in fetish gear. Then Gear Night hands over to Cock Shock with their infamous contest starting at midnight, things get very raunchy with these studs!
Sat Nov 4th
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 - Masc 4 Masquerade Ball, in aid of Queer Keys. SideBar, 504 Angela St. Mask up as we have a ball! Whether it's a masquerade mask, a pup mask, or a leather hood - get masc 4 mask as we dance the night away to hot beats raising money for Queer Keys.
Sun Nov 5th
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.
12pm to 4pm - Bears at Bourbon Pool Party. Bourbon St Pub Pool Garden (at rear), 724 Duval St. The last pool party of the weekend takes place at Bourbon St Pub hosted by a local drag queen and with shot boys walking around. Get your daily dose of fun in the sun on Sunday with the bears at Bourbon! Free entry!
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.
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.
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