Key West Bear Weekend 2025 – New Website & Schedule Reveal
The Key West Bear Weekend organizers are celebrating the start of the new year with a double reveal!
The Key West Bear Weekend website has been given a refresh to reflect their new bold, colorful branding! Go check it out at keywestbearweekend.com.There you’ll find all the info you need about getting around, passes, places to stay, and the 2025 schedule.
The schedule, as always, offers something for everyone, from pool parties to party nights, with themes including pirates, spooky halloween fetish night and a jockstrap party! Attendees will tell you, this is one of the friendliest and most inclusive bear runs out there.
Weekend passes are currently on sale and in the spirit of Key West’s famous ‘One Human Family’ motto, they are keeping things easy and friendly with their One Ticket Price. No add ons, no upgrades, just one easy price with everything a bear could want included.
Rooms always sell out fast, so make sure you check their official Accommodations list to get your reservation in.
Schedule
Wed, Oct 29th
12pm to 6pm – Wristband Collection
Island House, 1129 Fleming St.
Our volunteers are ready and waiting to welcome you to Key West Bear Weekend with your wristband!
12pm to 5pm – Bear Soup Pool Party
Island House, 1129 Fleming St.
The famous 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. The drinks are cool and the bears are hot! Included with KWBW weekend pass or $50 for Island House day pass.
5pm to 8pm – Dive-in Movie with Extended Happy Hour
Island House, 1129 Fleming St.
Kick off Key West Bear Weekend in style with our official first night party featuring a ‘dive-in’ movie watchable from in and around the Island House pool where it will also be an extended happy hour! Hotel guests receive a premium open-bar happy hour, and bears 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 to keep you entertained while you watch the movie. Included with KWBW weekend pass or $50 for Island House day pass.
Thurs, Oct 30th
12pm to 6pm – Wristband Collection
Island House, 1129 Fleming St.
Our volunteers are ready and waiting to welcome you to Key West Bear Weekend with your wristband!
12pm to 5pm – Welcome to Key West Rum Crawl
Starting at Island House lobby
Get into true Key West island life mode by joining us on this walking tour of Old Town Key West as we visit local rum distilleries for a taste of true Caribbean rum!
12pm to 5pm – Bear Soup Pool Party
Island House, 1129 Fleming St.
Another pool party beckons! Grab a swimsuit (or not!) and meet the rest of the gang. The drinks are cool and the bears are hot! Included with KWBW weekend pass or $50 for Island House day pass.
5pm to 6.30pm – Island House Happy Hour
Island House, 1129 Fleming St.
Island House happy hour is a Gay Key West MUST! Hotel guests receive a premium open-bar happy hour, and bears staying elsewhere enjoy 2-4-1’s on EVERYTHING!
Included with KWBW weekend pass or $50 for Island House day pass.
9pm to late – Jocktober Party
Bourbon St Pub Pool Garden (at rear), 724 Duval St
Strip down to your jocks and socks and dance the night away at Bourbon St Pub around their pool and garden with spot prizes for the best buns! Hosted by our special go-go guest, Ner!
Included with KWBW weekend pass or $15 cover
Fri, Oct 31st
12pm to 5pm – Bear Soup Pool Party
Island House, 1129 Fleming St.
Another pool party beckons! Grab a swimsuit (or not!) and meet the rest of the gang. The drinks are cool and the bears are hot! Included with KWBW weekend pass or $50 for Island House day pass.
10pm to late – Horny Halloween with Cock Shock
Saloon 1, 504 Petronia St
This is the HOTTEST and SPOOKIEST night of the weekend! Gear up, look scary and get down to Horny Halloween for two hours of sexy bears in spooky fetish gear as we lead into Cock Shock, a Key West institution, with their infamous contest starting at midnight… things get very raunchy with these studs! Included with KWBW weekend pass or $10 cover.
Sat, Nov 1st
11am to 1pm – Leather Master Shopping Experience
The Leather Master, 418 Appelrouth Lane
Check out this unique shopping experience which includes an open bar and clothing optional shopping. Leather, sex toys, hot bears, shopping and cocktails, who could ask for anything more?
2pm to 6pm – RED HOT Pool Party
Island House 1129 Fleming St.
Recover and recharge ready for the evening with this pool party with chill vibes and chilled cocktails! Included with KWBW weekend pass or $50 for Island House day pass.
10pm to late – Pirates of Men’s Pants, in aid of Queer Keys
Birdcage Cabaret (formerly known as Side Bar), 504 Angela St
Ahar me hearties! Key West has been at the center of pirate stories for centuries, so get ready to plunder some booty at our pirate-themed party! Your host Cap’n Ner is ready to help in your search for Poppers of Eight and to ensure your Roger is properly Jollied!
Queer Keys is an LGBTQ+ community organization based in Key West, Florida. Their mission is to support, educate, empower, and celebrate the queer community in the Florida Keys.
$20 cover (includes $5 donation to Queer Keys), included with KWBW weekend pass ($5 from every wristband sale will be donated to Queer Keys).
Please note: as this is a charity fundraiser in aid of Queer Keys that supports the full LGBTQ+ community, all genders will be welcome at this event.
Sun, Nov 2nd
12pm to 4pm – Island House Tea Party
Island House, 1129 Fleming St.
Our host hotel does what they do best on Sundays, as locals and visitors alike gather for this frisky clothing-optional shindig! Drink discounts, raffles, giveaways, drag queens, and free shots! Island House on Sundays is the place to be And attracts a big local crowd.
Included with KWBW weekend pass or $50 for Island House day pass.
5pm to late – Farewell Party
Island House, 1129 Fleming St
Chill out and relax at our farewell party. Wind down in style with a quiet pool, cool cocktails and chilled out music. Your last chance to say goodbye to friends new and old.
Included with KWBW weekend pass or $50 for Island House day pass.
Alongside the scheduled activities, make the most of your time around Key West by exploring the restaurants, shops and galleries. The Key West Bear Weekend wristband will provide a range of discounts and exclusive deals (more info to follow). Also, don’t forget to use the Duval Loop free shuttle service – more info here.
