Key West Bear Weekend Announced

Vacationer Staff
Written by Vacationer Staff

Key West is about to get beary this October when Shane Tate and Bear World Magazine join forces to hold the first Key West Bear Weekend, powered by Scruff. Come and join the bears in the sun from October 19th to 23rd! 

Check out the line up for the weekend and info on our partner hotel options below. 

Shane Tate is the man behind great NYC parties such as ‘Beers and Bears’, ‘NYC’s Original Beer Blast’, ‘Truck Stop’, ‘Furry Fridays’ and he also runs the hugely successful Fire Island Bear Weekend. Bear World Magazine is the world’s leading online magazine for the bear community, we know what bears want and the quality of event to put on. Together, Key West Bear Weekend promises to be one of the best bear runs you’ve been to!

Where to stay

Key West Bear Weekend offers several amazing partner hotel options, see below for info. These handpicked hotels all have outstanding ratings, offer incredible amenities and are within walking distance of all the Key West Bear Weekend events.

Island House Key West 

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. The large heated pool and jacuzzis are open 24 hours a day and their Health Club which includes a gym and Spa area with sauna, steam room and Jacuzzi is the most complete in Key West.

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

Island House is the host hotel for the weekend with many events happening here (see schedule below) so even if you are not staying here, you can still come along to enjoy the events. 

Click here to make a reservation.

Alexanders Guest House

Alexander’s Guesthouse is a lovingly restored Key West Conch house built in 1902, boasting beautiful, original pine floors and stately windows. Decorated with a tropical  elegance, a homey atmosphere is thoughtfully created. They are an LGBT guesthouse who also welcome friends of the LGBT Community promoting acceptance and respect for all.  

Click here to make a reservation.

LaTeDa Hotel Key West

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.

Click here to make a reservation.

There are many other lodging options available in Key West if you prefer to maximize your budget and stay a little further away from the center of town. Click here to see other hotel options and here to see Air B&B options

Weekend schedule 

Here is the weekend’s schedule, there are still events to be announced so be sure to check back.


Bears arrive in Key West and check in!


12pm til 5pm – Woof! Bear Soup Party

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. The Island House is located at 1129 Fleming Street.

5pm til 6:30pm – Greet The Meat Happy Hour

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 boy boyz. Start the weekend right by meeting the rest of our furry friends in an all-male, clothing optional oasis. Locks and lockers available. After the fun is the best time to head over to the kickoff of Fantasy Fest 2017, with the Bahama Village Goombay Festival right off the gayest block of Duval Street!  The Island House is located at 1129 Fleming Street

8pm til 11pm – 801 Bourbon Bar’s World Famous Cabaret Drag Show at 801 Duval St.

For over 25 years the Key West Drag Scene has been ruled over by the Grande Dame of Drag herself, Sushi!
You’ve seen her on CNN in her world famous “Red High Heel Shoe” hanging over the Bourbon St. Pub on New Year’s Eve. The drag extravaganza with a cast of 15 queens is not to be missed! Show starts at 9pm and 11pm.

You must reserve a table for this show in advance. Click here to make reservations 

12am til 4am – Cock ShockFridays at Saloon One (adjacent to 801 Bourbon) at 504 Petronia St.

Saloon One Key West’s leather bar hosts COCK SHOCK a raunchy night of fun with a contest awarding people up to $250 for the best: Couple, Ink, Chest, Butt, Ball and of course BEST COCK.


9pm til 4am – The Key West Bear Ball – Powered By Scruff, Key West Bear Weekend’s main event at the Side Bar 504 Angela Street

Presenting a night of fun, fetish and dance at Key West’s premiere night club Side Bar .

What makes you go WOOF? harnesses? Jocks? Uniforms? Singlets? come in what ever makes you feel sexy!

Dress for the hunt!  $10 cover.


12pm til 4pm – Bear Ass Tea

The Island House at 1129 Fleming Street, 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 cocktails, raffles, giveaways, drag queens, and free shots!

Whether your fighting the hair of the dog or you’re a pool party professional, Island House on Sundays is the place to be. After the 4pm raffle, be sure to join the rest of the Key West community for the Fantasy Fest Zombie Bike Ride, or watch the debauchery from Tea Dance at LaTeDa!

4pm til 6:30pm – La-te-da Bar World Famous Tea Dance

Come down to La-te-da Bar 1125 Duval Street and have a cock…tail and a twirl and get there early so you can get your spot on the deck to watch the Zombie Parade.

6pm – La-te-da Bar Zombie Bike Ride Viewing

One of Key West’s not to miss traditions. Started in 2009, this parade of wildly dressed zombies is truly a sight to behold. Come on down to La te da Bar at 1125 Duval Street and grab a cocktail or a bite to eat on their beautiful deck and watch the show.

9pm – Bear Beer Blast at 801 Bourbon at 801 Duval St.

$10 all you can drink beer!


Farewell bears, see you next year!

For more information, check out

About the author

Vacationer Staff

Vacationer Staff

Vacationer Magazine writing staff work hard to bring you all the latest LGBTQ travel articles to help inspire and inform.

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