Key West Bear Weekend 2026 Full Schedule
Key West Bear Weekend organizers have confirmed their full schedule for this year’s event in the island paradise of Key West!
The schedule, as always, offers something for everyone, from pool parties to party nights, with a Halloween Ball and a MANDATORY jockstrap party! New for 2026, the organizers have added a raft of new daytime activities including yoga, craft cocktail tour and clothing option boat cruises to add even more fun to the weekend.
Attendees will tell you, this is one of the friendliest and most inclusive bear runs out there.
All Access Passes are currently on sale with add-on available for the craft cocktail tour. Note, the Early Bird Rate of $150 ends May 31st, so grab passes soon before the price rise in June!
Schedule
Wed, Oct 28th
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 – Extended Happy Hour
Island House, 1129 Fleming St.
Kick off Key West Bear Weekend in style with the famous Island House 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. Included with KWBW weekend pass or $50 for Island House day pass.
8.30pm to 10.30pm – Dive-in Movie: Rocky Horror Picture Show
Island House, 1129 Fleming St.
Grab your feather boa and celebrate 50 years of this iconic movie on the big screen with our dive-in movie concept! Whether you’re Brad, Rocky or Frank, sing-a-long with all the classic songs with your fellow bears. Included with KWBW weekend pass or $50 for Island House day pass.
Thurs, 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!
10.30am to 2.30pm – Bear Cruise
Key West Historic Seaport
Set sail with BluQ on their clothing optional catamaran for 4 hours of sun, sea and salty surprises! Bring your own drinks and towel, and chill out with your fellow bears on this awesome Key West experience.
Please note, this must be booked directly with BluQ here. Also, this is not a private charter so places will be on a first-come, first-served capacity. So book quick!
1pm to 3pm – Craft Cocktail Tour
Start at Island House, 1129 Fleming St.
Get a taste of Key West with our guided tour of local Key West cocktail bars. Explore the city and the alcohol it runs on! Tour bus leaves Island House at 1pm, $25 covers transportation and guide cost, drinks not included. Limited to 20 people, pre-book this add-on during Pass checkout, or click Event Add-Ons.
2pm to 6pm – 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 choose whether to chill out by Bourbon St Pub around their pool and garden OR do you dare to venture into Ner’s playroom with used jock swap!
JOCKSTRAPS MANDATORY! Free clothes check.
Included with KWBW weekend pass or $15 cover
Fri, Oct 30th
1pm to 3pm – Bear Yoga
Island Mates Manor pool deck – through door at Island House Bar
Purge your sins of the night before with this yoga session led by an experienced instructor on the pool deck of the new Island Mates Manor next door to Island House. Limited to 20 people, sign-up on arrival at registration desk. Included with KWBW weekend pass or $50 for Island House day pass.
2pm to 6pm – Hats & Hoses Pool Party
Island House, 1129 Fleming St.
Sound the alarm! It’s our firemen’s pool party! Expect hard hats, long hoses and plenty of hot action in the pool! Included with KWBW weekend pass or $50 for Island House day pass.
10pm to late – Bad Bear with Cock Shock
Saloon 1, 504 Petronia St
Have you been a bad bear… Or do you want an excuse to be one?! This is the HOTTEST night of the weekend! Gear up and get down to Bad Bear for two hours of sexy bears in 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, Oct 31st
10.30am to 2.30pm – Bear Cruise
Key West Historic Seaport
This is your second opportunity to set sail with BluQ on their clothing optional catamaran for 4 hours of sun, sea and salty surprises! Bring your own drinks and towel, and chill out with your fellow bears on this awesome Key West experience.
Please note, this must be booked directly with BluQ here. Also, this is not a private charter so places will be on a first-come, first-served capacity. So book quick!
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 – Recovery Pool Party
Island House 1129 Fleming St.
Grab a swimsuit (or not!) and recover your energy with your fellow bears. The drinks are cool and the bears are hot! Included with KWBW weekend pass or $50 for Island House day pass.
10pm to late – Halloween Ball
Birdcage Cabaret, 504 Angela St
Get ready for a FRIGHTENING night of furry ghouls, goblins and other scary sights! Get your best Halloween costume together and dance the night away at the Birdcage Cabaret to spooky beats by our resident DJ. Spot prizes on offer for best costumes. $20 cover, included with KWBW weekend pass.
Sun, Nov 1st
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).
