From: Wednesday, Nov 3rd, 2021
To: Sunday, Nov 7th, 2021
Key West Bear Weekend 2021
The Bears don’t hibernate in the Winter.. the smart ones head to Key West every November,for a weekend of fun and relaxation!
Events take place across Key West and are open to everyone.
The Party kicks off on Wednesday with the Bears Arrival! Grab some cocktails at Island House.
- On Thursday, from 12pm to 5pm enjoy the Bear Soup Pool Party at the Island House on 1129 Fleming St. Grab a swimsuit (or not!) and meet the rest of the gang with lunch poolside, cool cocktails, and new friends. After, from 5pm-6.30pm join the Greet the Meat Happy Hour. The Island House Café will be whipping up tons of FREE gourmet appetizers, passed around poolside by their fabulous naked men.
- Later on Thursday from 9pm join the Beers and Bears Welcome Pool Party at Bourbon Street Pub 724 Duval St (Back pool area). Come out to share a few beers and cocktails to meet your fellow bears.
- Friday you are spoiled for choice. From 12pm to 5pm head to the Bear Soup Pool Party at Island House, or visit the VIP cocktail party, Alexander’s Guest House from 3pm-6pm.
- One of the big event highlights is the Mr Key West Bear Contest and Party which takes place at 9pm at The Bourbon Street Pub. Join the crowd to see the competition for the Mr Key West Bear title with celebrity guest host.
- Rise and Shine from 11am-1pm and take the 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?
- Later, time for another pool party, this time from 1pm-6pm. The Fuzzy Flamingo Pool Party takes place at Equator Resort on 822 Fleming St, Key West.
- From 9pm join the “Beers and Bears” party at Sidebar Key West on 504 Angela St. Get dressed up in your sexiest gear and get ready to dance.
- Our favourite day of the event, from 12pm-4pm check out the Bear Ass Tea Party at Island House where locals and visitors alike gather for this frisky clothing-optional shindig! $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. The event is followed by the farewell party which ends at 8pm.
OTHER BEAR PARTIES
Events such as Furball, world famous bear/gear dance party by Joe Fiore and the Butch bearded drag queen events at Aqua Nightclub have yet to be confirmed.
Where to Stay?
Most of the gay bars in town are clustered along colourful Duval Street so we have found hotel that keep you close,
Check out out Key West Gay Guide to find the best places to dine, party and play on the island.
Gay Map of Key West
Most of the gay bars in town are clustered along colorful Duval Street, in the historic district, which is also home to dozens of fun shops and inviting restaurants.
Recommended Apartments in Key West
The holiday home includes a Living room with TV, a kitchen with a dishwasher and a coffee machine. There is a bathroom with a shower and hairdryer. A Private swimming pool and a barbecue. Free WiFi
This Air conditioned holiday home has a living room with satellite TV, a fully equipped kitchen with an oven and a microwave, 2 bedrooms and a bathroom with shower. A swimming pool and a Barbecue. Free WiFi
This Air conditioned holiday home includes a living room with a TV with satellite channels, a kitchen with a dishwasher and an oven, as well as a coffee machine and a washing machine. A Swimming pool & Free WiFi
Featuring air-conditioned accommodation with a private pool, 3 bedrooms, a TV with cable channels, an equipped kitchen with a dishwasher and a microwave, a washing machine, and 4 bathrooms with a shower.
Video of Key West Bear Weekend
Key West Bear Weekend Highlights.
Recommended Hotels in Key West
Check out a selection of our favourite hotels in Key West, close to all of the gay bars and clubs and offering great service and value for money.
3 Star, Adult Only
10 bedroom guest house with an outdoor heated pool, continental buffet breakfast, and free WiFi.