Event Dates
From: Wednesday, October 30, 2024
To: Sunday, November 3, 2024
The Bears don’t hibernate in the Winter.. the smart ones head to Key West every November.
The Bears don’t hibernate in the Winter.. the smart ones head to Key West every November, for a weekend of fun and relaxation!
- Stay close to the pool parties and daytime events at Alexander’s Guest house, an adults only hotel rated “Exceptional” by guests with charming rooms and superb hosts.
The Bear Weekend
- Wednesday Oct 30th – Sunday Nov 3rd, 2024 – Events take place across Key West and are open to everyone. Some of the island’s most popular gay venues host a series of pool parties, night time events and bear gatherings. Island house plays host to the both the welcome event on Wednesday at 5 pm and the Farewell party on Sunday at 6 pm.
- Stay at the adults-only Porch on Frances Inn, rated “Exceptional” by guests with a perfect locations, beautiful rooms and a warm Key West welcome.
The Pool Parties
- Events kick off on Wednesday From 12 pm to 5 pm with the Bear Soup Party at Island house. Grab a swimsuit (or not!) and meet the rest of the gang with lunch poolside, cool cocktails, and new friends.
- Pool parties continue on Thursday & Friday afternoons at Island House.
- Events end on Sunday with the “Bear ASS Tea Party” described as a frisky clothing-optional shindig!
Mr Key West Bear Contest
- Friday – Join the crowd at Bourbon Street Pub from 9 pm to see the competition for the Mr Key West Bear title with celebrity guest host. The winner of this contest receives a $200 cash prize and a handmade leather sash courtesy of Leather Master.
- Bourbon Street Pub – New Orleans-themed gay destination for theme nights, drag shows & outdoor pool with bar & theater. The famous men only clothing optional garden pool is a true Key West experience, as are the nightly Men of Bourbon shows.
Night Time Events
- Thursday – Head to Sidebar for the Bear World Magazine Party from 9pm
- Friday – Bourbon Street Pub hosts the Bear in a Jockstrap Night time pool event from 10.30pm, a post Mr Bear Key West event.
- Saturday – Key West Leather Ball takes over Sidebar Key West. Dress is your sexiest gear and dance all night long.
- Sidebar – Located on Duval Street, Sidebar is the only dance club on the island and hosts nightly theme parties, live DJs and the hottest late night dance floor.
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 during Key West Bear Weekend?
Most of the gay bars in town are clustered along colourful Duval Street so we have found hotel that keep you close,
Duval Gardens, Truman Hotel, The Gardens Hotel, Paradise Inn
Check out out Key West Gay Guide to find the best places to dine, party and play on the island.
Where to stay close to all the gay bars.
Our top 4 selections with the best rates.
The Paradise Inn is our favourite place to
stay when in Key West. Great location
For further information and advice on
Key West Bear Weekend, Website
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.
Book with confidence. Get the best Prices from our partner Booking.com
We have chosen hotels in Key West that keep you close to all the shops, restaurants, bars & fun
Key West Bear Weekend Highlights.