Key West Bear Weekend 2025 – Photo Recap!
Key West Bear Weekend 2025, hosted by GoGo Ner & Puddin’ Taine, was another amazing success with over 150 bears in attendance across the weekend having a blast at the Island House Resort, and various locations across the city.
We kicked off with the Bear Soup pool party and extended happy hour with welcome appetizers to help us all catch up or meet new friends.
The Dive-In Movie Night (Wednesday) was of course the camp horror classic Scream, and we got the chance to start to get to know each other and reconnect with friends.
Thursday daytime saw everyone back in the pool, with another Bear Soup pool party as more bears arrived, follow by another fun happy hour.
Thursday night saw the debut of our new party Jocktober and Jock Swap at Bourbon Street Bar with DJ Angel and hosted by ‘Piggy Taine’ (Puddin’ Taine) and Ner! Lots of bears were seen in jocks, and if you didn’t have a jock, we had many new ones supplied by Tulken Gear, as well as some used ones supplied by our bears! Everyone that wanted to be in a jock got a chance – we still have some left that will be ready for next year! Jocks were given out for Best Ass, Burliest Bear, and Ripest Jock too!! Well done bears and thanks to Tulken Gear!
Friday, which was Halloween, kicked off with a Cowboy pool party and more prizes given away from the night before. Two well worn and sweaty jocks were given out – one worn by GoGo Ner and one anonymous, very sweaty one! Our game of pass the beachball was taken seriously for these wins! More jocks from Tulken Gear were given out too to make the bears very happy!
At night we all headed to Saloon 1 for a hot night with the ever popular Cock Shock (a Key West staple) with prizes for some of our bears.
Saturday morning meant shopping, so we all headed to the clothing optional shopping experience at Leather Master. As ever, we were able to shop with a Bloody Mary or Mimosa in hand and wearing very little! David was on hand to make sure that cock rings were fitting perfectly too! Once again, a very popular event!
Saturday at the pool was sponsored by the Bottoms Up Movement, with tons of giveaways. Ner hosted poolside and sorted the Tops from the Bottoms!
Saturday night, we dressed up as Pirates for Pirates in Men’s Pants, and had fun dancing to a 4-hour set from DJ Angel while benefitting local charity, Queer Keys.
Sunday we joined in with the Island House Sunday Pool Party with shots, prizes, and a full bar – not to be missed every Sunday!
What an exceptional week it was with so many bears from all over the USA, and a few from overseas. We will all see you next year. Super Early Bird Rate passes are already available, you can get info on that and sign up for our newsletter at keywestbearweekend.com
Event photography by Tristan Sutphin and full event photos coming soon!
