Event Dates
From: Wednesday, November 1, 2023
To: Sunday, November 5, 2023
Key West Bear Weekend 2023
The Bears don’t hibernate in the Winter.. the smart ones head to Key West every November
Key West Bear Weekend 2023
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
- 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 Spop 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. Don’t miss the Friday “Cybersocket” party hosted by Alexander Rodriguez and XXX Bear-icon Teddy Bear!
- 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 Alexander Rodriguez! 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.
Recommended Hotels
Where to stay close to all the gay bars.
Our top 4 selections with the best rates.
Where we stay!
The Paradise Inn is our favourite place to
stay when in Key West. Great location
Official Website
For further information and advice on
Key West Bear Weekend, Website
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 Hotels in Key West By Booking
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
The Gardens Hotel
4 Star, adults-only
this adult-only hotel offers two outdoor pools. Duval Street is a 1-minute walk away, and Key West Butterfly and Nature Conservatory is 3 minutes’ drive from the hotel. A private balcony or patio with property views is provided in all rooms at The Gardens Hotel Key West. A flat-screen cable TV, ironing facilities, and a refrigerator
Paradise Inn
3 Star, Adult Only
Paradise Inn – Adult Exclusive is located in Key West and features landscaped grounds with brick paths and a lotus pond with koi and tropical turtles. A complimentary continental breakfast is served in the lobby. The suites at Paradise Inn – Adult Exclusive include a sitting area with cable TV. A microwave, refrigerator, and coffee facilities
Douglas House
3 Star, Adult Only
Located just 2 minutes’ walk from the Ernest Hemingway Home and Museum, this adult-only inn features free parking and a shared outdoor swimming pool. Free Wi-Fi is also available. A microwave, refrigerator and coffee-making facilities come standard in each room
Truman Hotel 3 Star
Trendy Boutique
This trendy Key West boutique hotel features an outdoor pool and modern rooms equipped with iPod docking stations and flat-screen TVs. All rooms at the Truman Hotel are equipped with a refrigerator. Each room is styled with wood floors, and bathrooms boast tiled showers and marble vanities.
Video of Key West Bear Weekend
Key West Bear Weekend Highlights.
Recommended Hotels in Key West BY Expedia
Book with confidence. Get the best Prices from our partner Expedia
We have chosen hotels in Key West that keep you close to all the shops, restaurants, bars & fun
Hyatt Centric
4 Star, Great Pool
At Hyatt Centric Key West Resort and Spa, hit the nearby beach, relax by an outdoor pool, or spend the day at a marina. All 120 soundproofed rooms feature iPod docks and room service. Guests will appreciate conveniences like sitting areas and coffee makers, while flat-screen TVs with satellite channels
Ocean Key Resort
4 Star, Stylish
2 restaurants, a full-service spa, and an outdoor pool are available at this smoke-free resort. WiFi in public areas is free. Other amenities include 3 bars/lounges, a poolside bar, and valet parking. All 100 individually decorated rooms feature free WiFi and iPod docks. For a bit of entertainment, guests will find LCD TVs with satellite channels
The Cabana Inn
3 Star, Readers Choice
An outdoor pool, a snack bar/deli, and a spa tub are available at this guesthouse. Other amenities include self parking, coffee/tea in a common area, and a business center. All rooms are individually decorated and offer free bottled water and ceiling fans. For a bit of entertainment, flat-screen TVs come with cable channels
The Saint Hotel
3 Star, Modern Classic
Along with a restaurant, this smoke-free hotel has an outdoor pool and a 24-hour fitness center. WiFi in public areas is free. Other amenities include a bar/lounge, a rooftop terrace, and valet parking. All 36 individually decorated rooms provide free WiFi, free wired Internet, and iPod docks. LCD TVs with digital channels
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