Key West Bear Weekend Official Events

All event times subject to change. We also will be adding events so stay tuned.

All events hosted at hotels are open to everyone with KWBW passes whether your staying at that hotel or not. 

 

KWBW Passes are the best value. All events and amenities come to $195 if purchased individually.

Wristbands are available  for purchase or pickup during scheduled collection times or at the entrance to each event listed in pink below. If you need to arrange  a special pickup time please email shane@keywestbearweekend.com

Wed Nov 3rd

Bears arrive in Key West!

2pm-7pm – 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 infamous 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, cool cocktails, and new friends. Included with KWBW weekend pass or $30 for Island House day pass.

5pm-6.30pm – Happy Hour @ Island House 1129 Fleming St.

Island House happy hour is a Gay Key West MUST!

Included with KWBW weekend pass or $30 for Island House day pass

Thurs Nov 4th

11am-7pm – 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 infamous 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, cool cocktails, and new friends. Included with KWBW weekend pass or $30 for Island House day pass.

 

5pm-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 an premium open-bar happy hour, and men 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. Start the weekend right by meeting the rest of our furry friends in an all-male, clothing optional oasis. Locks and lockers available. Included with KWBW weekend pass or $30 for Island House day pass.

9pm – Britney vs Madonna Dance Party, Sidebar Key West, 504 Angela St. Key West.

Come out to share a few beers and cocktails to meet your fellow bears.

Included with KWBW weekend pass or $5 cover

 

Fri Nov 5th

 

12pm to 5pm – Bear Soup Pool Party @ Island House 1129 Fleming St.

Island House plays host to another pool party! Grab a swimsuit (or not!) and join your fellow bears poolside for food, cocktails and new friends. Included with KWBW weekend pass or $30 for Island House day pass.

 

3pm-6pm – VIP cocktail party, Venue TBD

Bear World Magazine invites our VIP pass holders to an exclusive cocktail pool party with performances by the very talented VITA SUMMERS. Included only with KWBW VIP weekend pass.

9pm – Mr Key West Bear Contest and Party, Bourbon Street Pub 724 Duval St (Cabaret Room)

Join the crowd to see the competition for the Mr Key West Bear title with celebrity guest host! The winner of this contest receives a $200 cash prize and a handmade leather sash. Mr. Key West Bear will be expected to raise money and / or raise awareness for a local Key West LGBTQ cause, however you are not required to be a Key West resident. For more information on entering the contest visit www.keywestbearweekend.com

Included with KWBW weekend pass or $5 cover.

POOL PARTY after the contest in the back area behind Bourbon Street Pub after 10:30pm till close


 

Sat Nov 6th

11am-1pm Leathermaster Shopping Experience

The Leather Master at 418 Appelrouth Lane is offering a unique shopping experience to our bears which includes an open bar and clothing optional shopping. Come on down and get all the supplies you need for FURBALL! Leather, sex toys, hot bears, shopping and cocktails, who could ask for anything more?

 

1pm-6pm Fuzzy Flamingo Pool Party @ Equator Resort 822 Fleming St, Key West.

Bears invade the Equator Resort for fuzzy fun in the sun. Pool party, music, drinks all the hot bears you can handle! Included with KWBW weekend pass or $10 cover.

9pm – Beers and Bears Leather Ball @ Sidebar Key West, 504 Angela St. Key West.

Bear World Magazine invites you to their Beers and Bears. Get dressed up in your sexiest gear and get ready to dance. $15 cover, included with KWBW weekend pass.
 

Sun Nov 7th

 

12pm-4pm – Bear Ass 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! Music videos, $4 New Amsterdam Vodka and $5 Stoli cocktails, raffles, giveaways, drag queens, and free shots! Whether you’re fighting the hair of the dog or you’re a pool party professional, Island House on Sundays is the place to be. Included with KWBW weekend pass or $30 for Island House day pass.

 

6pm-8pm – 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 $30 for Island House day pass.