EventsKey West Bear Weekend

Here’s what to look forward to at Key West Bear Weekend in November!

Key West Bear Weekend is BACK, and the dates are set for NOVEMBER!

After two years of pandemic cancellations, Shane Tate Presents Key West Bear Weekend, returns in 2022! The very popular and VERY HOT Bear weekend, sponsored by and Bear World Magazine, will be held from November 2nd to November 6th, and will be a perfect way to heat up your late autumn! 

Join the Bears in the hottest location in Florida for some fun and frolics in the sun! This year’s events will include tons of pool parties and happy hours, along with the Britney Vs. Madonna Dance Party, the Fuzzy Flamingo Pool Party, the Beers and Bears Leather Ball and the Mr. Key West Contest and Dance Party! 

Key West Bear Weekend is ALWAYS an amazing time! Just scroll through some of these fantastic shots from Key West Bear Weekend 2019!


We have some amazing events lined up for your furry pleasure this year. Take a look at our schedule for all the hot, fuzzy fun you have to look forward to! 

​Wednesday and Thursday, November 2nd and 3rd

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 $40 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 $40 for Island House day pass).

Thursday, November 3rd

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 $40 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).

Friday, November 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 $40 for Island House day 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 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.

Saturday, November 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 

@ 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.

​Sunday, November 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 $40 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 $40 for Island House day pass.

Special Guests

We are excited to announce two very special guests this year who will be bringing sass and sexyness in equal measure to the weekend. You may know them as the Co-Hosts from the wonderful podcast Bear With us Gurrrl they are of course on-air personality Alexander Rodriguez and the furriest of bear models, Teddy Bear. 

They will be also representing Cybersocket, and recording some fun stuff for the podcast, so watch out for them across the weekend. Alexander will also step into the hosting shoes for the Mr Key West Bear Contest and Teddy Bear will be an extra special guest judge alongside our regular judges.

Alexander Rodriguez (left) & Teddy Bear (right)

Alexander Rodriguez, the love child of  Joan Rivers, Johnny Carson and Judy Garland. Is a true renaissance man, he wouldn’t be caught dead without his signature suit, loud tie, matching pocket square, and a cocktail (or two) in hand. Alexander’s sense of humor shines through in his cabaret shows (when he can remember the words), daily life, and his nationally syndicated radio show “On The Rocks with Alexander: Where Celebrities & Cocktails Mix” on iHeartRadio, Pandora, and Spotify. 

He chats with big-name guests from classic to current Hollywood, reality TV, pop culture and music, meshing celebs from all walks of life to draw together a truly diverse listener base regardless of age, orientation or gender.  

“Sun, bears, and Key West? Yes, please! I’m thrilled to join the festivities for Key West Bear Weekend with my community. If you’ve been to any bear event with Bear World Magazine, you know the inclusivity, freedom, and fellowship that can be found…plus a dash of sass and sexiness. I’m ready, where’s my speedo?”

Teddy Bear is known for being the hairiest guy on OnlyFans, and he takes that title with a sense of pride. Having been shamed for being hairy most of his life, he not only turned that shame into pride, but into a business. With his OnlyFans page and Bear themed merch shop, Teddy Bear USA. Having been in the adult industry for 5 years now, he encourages Body Positivity in his fans by letting them know they should “Embrace the Fur” and have no shame in having say a hairy back (or more). 

Tickets and Passes

KWBW Passes are the best value. All events and Island House amenities come to $245 if purchased individually. Pass options include: 

This pass includes entry to all official events during Key West Bear Weekend.

Daily access to the Island House Key West Resort guest facilities which include: Pool, gym, hot tub, sauna and their legendary play room. WOOF! ($200 Value)

This pass includes entry to all official events during Key West Bear Weekend.

Daily access to the Island House Key West Resort guest facilities which include:  Pool, gym, hot tub, sauna and their legendary play room. WOOF! ($200 Value)

This pass also includes instant access to all events, no waiting in lines, and a private VIP cocktail party. 


Returning as the event’s host hotel is Island House Key West. The Island House Resort’s luxurious guest facilities are available to all KWBW ticket holders even if you’re not staying at the Island House Resort. Find out more below about all KWBW hotels! 

Island House Key West

The Island house is the host hotel of Key West Bear Weekend. 

Island House is an award-winning gay resort in Old Town Key West, set in a completely secure private compound where the choice to wear something, or nothing at all, is yours.

Their large heated pool and jacuzzis are open 24 hours a day. Their Health Club which includes a gym and Spa area with sauna, steam room and Jacuzzi, is the most complete in Key West.  10% off all returning hotel guests.

Their café, which has been rated one of the best in Key West, serves breakfast, lunch, dinner, and an overnight menu poolside. Thier menus feature American favorites with Caribbean touches. The bar offers beer, wine, champagne, mixed drinks, and tropical specialties all day and all night.

They will host a free happy hour every evening which is quite festive, and provides an opportunity to get to know other guests. 

To book, visit or call 1-800-890-6284.

New Orleans House

The New Orleans House is the only all gay, all male guest house on Duval Street. Located in the heart of old town Key West. You will be just steps away from everything Key West offers.

To book, visit

Equator Resort

At the Equator Resort they believe all the typical male-only resort expectations can be met without sacrificing class or service. 

Now complete that with an all-male, clothing optional environment that prides itself in guest privacy and comfort. Tucked away in the heart of Old Town Key West, the Equator Resort is just 3 blocks from Historic Duval St. Providing easy access to a city filled with history, culture, festivity and most of all relaxation.

The resort offers a large, lush and open private setting with two heated pools and two hot tubs. Comprised of 5 historic properties each room is unique and offers its own charm all with private baths and spacious rooms. 

To book, visit

La-Te-Da Hotel

Over the years La-Te-Da has evolved into one of the most sophisticated venues in the Keys, while meticulously maintaining a true old-world Key West style. The tradition of excellence is stronger than ever at La-Te-Da, offering beautifully appointed guestrooms, great entertainment, gourmet dining and exciting bars, all cared for by a warm and courteous staff.

Rooms are being held exclusively for Key West Bear Weekend. 

To check availability and to book, you MUST call the reservations line as they will not show up online – (305) 296-6706.

Kimpton Key West – Fitch Lodge

Minutes from the action, Fitch Lodge welcomes on-the-go explorers to authentic conch-house lodging in a neighborhood setting. The Lodge has 44 rooms with daily events, a boozy arrival drink when checking in, free rental bikes and a complimentary continental breakfast served daily. Fitch Lodge is a five minute walk from Island House, home base of Key West Bear Weekend. 

Click here to visit the site and book now! 

Alexander’s Guesthouse

We are an LGBTQA guesthouse which means all humans are welcome, of course, but they also hold an especially safe space for members of the Lesbian, Gay, Bi, Trans & Queer groups. They welcome all Allies as well!

They love all Humans, and in Key West they live by the inclusive motto that we are “One Human Family!”
To book, visit

Key West Bear Weekend tickets and passes are ON SALE NOW! CLICK HERE to find out more about All Access and VIP Gold passes! 

For more information about Key West Bear Weekend, visit

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Find all about Alexander & Teddy Bear at

Key West Bear Weekend is sponsored by Bear World Magazine and

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