Key West Bear Weekend 2018 Schedule & Accommodation Updates

Vacationer Staff
Written by Vacationer Staff

Key West Bear Weekend returns this Fall, Thursday, November 8th – Monday, November 12th 2018, and the organisers have just announced the exciting schedule for the weekend, along with accommodation updates.

The host hotel for Key West Bear Weekend, Island House Resort, has SOLD OUT of rooms for the weekend! However, there are rooms still available in the other partner hotels, but get them booked soon to avoid disappointment!

Alexander’s 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. It is located opposite the Island House Resort, so perfect for access to the host hotel.

Visit to book.

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. New Orleans House is also the host venue of Key West Bear Weekend’s Bubble Bear Foam Party!

Visit to book.

Equator Resort

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 2 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.

Visit to book

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.

Visit to book.

Key West Bear Weekend 2017 (Photo: Larry Blackburn)


Thursday November 8th

Bears arrive in Key West and check in!

Friday November 9th

12pm-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-6:30pm – Greet The Meat Happy Hour

Island House happy hour is a Gay Key West MUST! Hotel guests receive a 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. Lockers available.

10pm-2am – Bubble Bear Foam Party

Bear Word Magazine hosts the Bubble Bear Foam Party at the world-famous Bourbon Street Pub at 724 Duval Street. Go-go dancers, Live DJ’s, a pool and a hot tub filled with hot bubbly bears make for one of Key West Bear Weekend’s hottest events. WOOOF!! $10 cover, included with the KWBW weekend pass.

Saturday November 10th

11am-1pm – The Leather Master Shopping Experience

The Leather Master at 418 Appelrouth Lane is offering a unique shopping experience 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-3pm – Bear Arts & Crafts Reception

Dog Tired Studio is open all weekend with BEAR focused art, crafts and artists. Join us for an exclusive reception to enjoy bear arts and crafts along with some surprises. The Dog Tired Studio is at 1011 Whitehead Street.

7pm-8pm – Gun Oil Cocktail Party

Gun Oil Lube brings you The Gun Oil Cocktail Party at the Back Bar, 711 Duval Street, featuring an outdoor bar with Gun Oil giveaways and prizes. Also, you will be able to meet the contestants of the Mr. Key West Bear Contest hosted by Mr. Fire Island Bear 2017 Dan Jimenez. $5 cover, includes Mr Key West Bear Contest, included with the KWBW weekend pass.

8pm-9pm – The Mr. Key West Bear Contest

The Leather Master Key West welcomes you to the first ever Mr. Key West Bear contest, hosted by Mr. Fire Island Bear 2017 Dan Jimenez. The winner of the contest receives a $200 cash prize and a handmade leather sash. Mr. Key West Bear will be expected to raise money for local Key West LGBTQ charities, however you are not required to be a Key West resident. For more information on entering, email [email protected]. $5 cover, included with the KWBW weekend pass.

9pm-4am – FURBALL Key West, powered by SCRUFF

Key West Bear Weekend is proud to host the debut of Joe Fiore’s world-famous bear/gear party in Key West as our Main Event of the weekend. Come along to Side Bar, 504 Angela Street. $20 cover, included with KWBW weekend pass.

Sunday November 11th

12pm-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 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 the KWBW weekend pass.

7pm-9pm – Butch Queen Bar Crawl

Beards and Bears get ready to sissy that walk! Category is, Bearded Butch Queen Realness! Get dressed up in your fiercest bearded/butch queen looks. We meet at the Aqua Nightclub, 711 Duval Street, at 7pm for cocktails to work up our nerve then we hit the town at 8pm sharp for an epic bar crawl! Drag is not required but encouraged. Also, comfortable shoes are recommended for those cobblestone streets… don’t be a hero! Included with KWBW weekend pass.

9pm – Bear Beer Blast

$10 all you can drink beer at 801 Bourbon, 801 Duval St. Come and say farewell to your new bear friends and toast a great weekend in paradise!

For more information on the full line up, visit

Key West Bear Weekend 2017 (Photo: Larry Blackburn)


Key West Bear Weekend All Access Pass – $65

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

  • Daily access to the Island House Resort guest facilities which include: pool, gym, hot tub, sauna and their legendary play room… woof!
  • Exclusive discounts and deals both around Key West and online

Key West Bear Weekend Gold Pass – $85 SOLD OUT!

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

  • Daily access to the Island House Resort guest facilities which include: pool, gym, hot tub, sauna and their legendary play room… woof!
  • Catered VIP areas at participating venues
  • Instant access at all KWBW events, no lines!
  • Exclusive VIP discounts and deals both around Key West and online

To purchase your passes, click here


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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