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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 $300 if purchased individually or not discounted.

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 Nov 1st

2pm 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 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.

 

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 – Greet the Meat 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! 

 

To greet the meat, the Island House Café will be whipping up tons of FREE gourmet appetizers, 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.

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! 

 

Included with KWBW weekend pass or $10 cover

​ 

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! 

 

Pay as you go on the pies, but there will be some freebies waiting along the way! Meet at the Island House lobby to start the tour. 

 

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. 

 

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.

 

$15 cover (includes $5 donation to Queer Keys), included with KWBW weekend pass ($5 from every wristband sale will be donated to 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. 

 

Included with KWBW weekend pass or $50 for Island House day pass.

 

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. 

 

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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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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