Key West Bear Weekend 2026

Key West Bear Weekend 2026

Bears, sunshine and very little clothing. Key West Bear Weekend brings five days of pool parties, jockstrap nights, Halloween celebrations and relaxed island socialising to one of America’s most gay-friendly destinations.

• 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 Event

• Next Edition: Wednesday, October 28, 2026 To Sunday, November 1, 2026.
• Highlights: Bear Soup pool parties, Jocktober, Hats & Hoses, Bad Bear, Halloween Ball and Sunday Tea Dance.
• Most of the events take place around the pool of the Island House pool.
• Other Venues: Bourbon Street Pub, Saloon 1 and Birdcage Cabaret.
• New for 2026: Bear yoga, craft cocktail tours and clothing-optional catamaran cruises.
• The weekend combines daytime gatherings at Island House with themed parties across Old Town.
• Mix and mingle with easy going crowd of bears, cubs, admirers and friends.
• Check out the top 10 hotels in Key West. 

The 2026 Program

Date & Time	Event	Venue
Wednesday 28th October 2026
12:00-17:00	Bear Soup Welcome Pool Party	Island House. Opening afternoon pool party to kick off the weekend.
14:00-18:00	Wristband Collection	Island House. Collect your weekend pass.
Thursday 29th October 2026
10:30-14:30	BluQ Bear Cruise	Key West Historic Seaport. Clothing-optional sailing excursion.
12:00-18:00	Wristband Collection	Island House. Weekend pass collection.
13:00-15:00	Guided Craft Cocktail Tour	Departs Island House. $25 supplement; drinks charged separately.
14:00-18:00	Bear Soup Pool Party	Island House. Afternoon pool party with music and drinks.
17:00-18:30	Happy Hour	Island House. Early evening drinks and socialising.
21:00-late	Jocktober	Bourbon Street Pub pool garden. Jockstraps mandatory; complimentary clothes check.
Friday 30th October 2026
13:00-15:00	Bear Yoga	Island Mates Manor, accessed through Island House.
14:00-18:00	Hats & Hoses Pool Party	Island House. Firefighter-themed afternoon pool party.
22:00-late	Bad Bear & Cock Shock	Saloon 1. Late-night bear party with the Cock Shock competition from midnight.
Saturday 31st October 2026
10:30-14:30	BluQ Bear Cruise	Key West Historic Seaport. Second clothing-optional sailing excursion.
11:00-13:00	Leather Master Shopping Experience	418 Appelrouth Lane. Leather and fetish shopping.
13:00-15:00	Bear Yoga	Island Mates Manor, accessed through Island House.
14:00-18:00	BEAR Magazine Pool Party	Island House. Afternoon party with giveaways and merchandise.
21:00-late	Halloween Ball	Birdcage Cabaret, 504 Angela Street. Halloween costumes, dancing and prizes.
Sunday 1st November 2026
12:00-16:00	Island House Tea Party	Island House. Drag queens, drinks promotions, raffles and giveaways.
From 17:00	Farewell Party	Island House. Poolside cocktails and relaxed music to close the weekend.

Weekend Passes

• All Access Pass: $175, with the early-bird offer now finished.
• Includes admission to official pool parties and evening events.
• Daily access to Island House facilities, including its pool, hot tubs, gym, sauna and playroom.
• Discounts at selected local businesses.
• Refunds available until 30 days before the event.
• Selected activities, including the cocktail tour and BluQ cruises, require separate bookings.
• Book official Key West Bear Weekend passes.

The Venues

Island House Key West

• Island House is the social centre of the weekend, a men-focused, clothing-optional resort on Fleming Street.
• Its tropical courtyard surrounds a heated pool and hot tubs, with a bar, café, sauna, gym and playroom. The atmosphere changes throughout the day, from laid-back afternoons on the loungers to busy pool parties and evening gatherings.

Bourbon Street Pub

• Bourbon Street Pub, 724 Duval Street, is one of Key West’s longest-running gay nightlife venues.
• The indoor bar hosts music and entertainment, while the rear garden has an outdoor pool, bar and men-only clothing-optional areas. The Jocktober party makes full use of this layout.

Saloon 1

• Saloon 1, at 504 Petronia Street, is Key West’s established men’s leather and cruise bar.
• Expect a darker, more intimate interior than the Duval Street show bars, with a relaxed attitude to fetish clothing and a crowd that gets progressively more adventurous after midnight.

Birdcage Cabaret

• Birdcage Cabaret, at 504 Angela Street, is part of the Aquaplex entertainment complex.
• The venue combines a performance space with a bar and dance floor, hosting drag shows, DJs and themed club nights.

Before the Party

Old Town is compact enough to enjoy a few drinks before the evening events.

• 801 Bourbon Bar – A Key West institution on Duval Street, with an upstairs drag theatre, downstairs bar and a lively mix of locals and visitors.
• Bobby’s Monkey Bar – An unpretentious neighbourhood bar on Simonton Street, known for karaoke, inexpensive drinks and a loyal local crowd.
• 22&Co – A small cocktail bar on Angela Street, with inventive martinis and a playful, sociable atmosphere. Convenient before events at Birdcage Cabaret.

Where to Stay for Key West Bear Weekend

Stay in Old Town, preferably between Fleming Street and Duval Street, for easy access to Island House and the evening parties. Key West’s historic guesthouses offer a more personal alternative to the larger waterfront resorts.

• The Gardens Hotel – An adults-only boutique hotel set around tropical gardens and two pools, just off Duval Street. Individually decorated rooms, private patios and a peaceful courtyard provide a welcome contrast to the nightlife outside.
• Paradise Inn – An adults-only inn on Simonton Street, with spacious suites, a pool, hot tub and complimentary breakfast. Its quieter residential setting works well for recovering between parties without being far from the bars.
• Douglas House – An adults-only guesthouse near the Hemingway House, with a pool, garden terraces and a good choice of room sizes. Particularly appealing for guests who want the atmosphere of a traditional Key West property rather than a conventional hotel.
• Truman Hotel – A contemporary boutique hotel on Truman Avenue with modern rooms, a courtyard pool and breakfast included. Convenient for southern Duval Street and the bars around Petronia Street.

Getting Around Key West

Most Old Town venues are within walking distance of one another. Island House is farther north than the main Duval Street bars, so allow approximately 15 to 20 minutes to walk between them.

The free Duval Loop bus is another option for travelling around Old Town. Taxis and rideshares are useful late at night.

Other Key West Bear Events

Can’t make the October weekend? WOOF Week Key West returns from Tuesday 13th April to Sunday 18th April 2027, with another programme of bear parties and social events.