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 $285 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 2nd

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 $50 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 $50 for Island House day pass

Thurs Nov 3rd

 

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 $50 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 $50 for Island House day pass.

9pm – Bear World Magazine's 10th Birthday Party Sidebar Key West, 504 Angela St. Key West.

Come and celebrate Bear World Magazine turning 10 with beers, cocktails and a few birthday surprises too!

Included with KWBW weekend pass or $10 cover

 

Fri Nov 4th

 

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

Cybersocket presents a 'let's get naked' pool party hosted by Alexander Rodriguez and XXX Bear-icon Teddy Bear! Join your fellow bears poolside for food, cocktails and fun! Included with KWBW weekend pass or $50 for Island House day pass.

6:30 pm - The 3 Bears Comedy Show

Comedy Key West  218 Whitehead Street, Key West (not included with weekend passes)

For more information and tickets click here.

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 Alexander Rodriguez! The winner of this contest receives a $200 cash prize and a handmade leather sash courtesy of Leather Master.

 

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 our entry page

 

Included with KWBW weekend pass.

10:30pm - Bear In A Jockstrap Pool Party @ Bourbon Street Pub 724 Duval

Join your fellow bears in celebrating the new Mr Key West Bear 2022 after the contest with late night poolside fun in your jock! Included with KWBW weekend pass or $10 cover.


 

Sat Nov 5th

 

11am-1pm Leathermaster Shopping Experience The Leather Master, 418 Appelrouth Lane

Check out this unique shopping experience which includes an open bar and clothing optional shopping. Come on down and get all the supplies you need for the Leather Ball! Leather, sex toys, hot bears, shopping and cocktails, who could ask for anything more?

3pm-6pm – Key West Bear Weekend VIP cocktail party hosted by Beatrix @ Alexander's Guesthouse 1118 Fleming St.

Bear World Magazine invites our VIP pass holders to an exclusive catered BBQ & cocktail party with guest DJ and hosted by Mr Key West Bear Weekend sash holders. Included only with KWBW VIP weekend pass.

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

It's time to get dressed up in your sexiest gear and get ready to dance! $15 cover, included with KWBW weekend pass.
 

Sun Nov 6th

 

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 $50 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 $50 for Island House day pass.

Looking for something quieter? 

All weekend KWBW pass holders can head to the Equator Resort for some quiet chill out pool time with bring your own alcohol.