San Juan Bear Weekend
About This Event
San Juan Bear Weekend is a relatively new affair, a five-day getaway to Puerto Rico's capital organized by Bear Milk, a bear party crew from New York. It debuted in February 2025, and the second edition took place from 12 to 16 February 2026. For East Coast bears, it's a winter escape - not a long-standing local tradition.
The 2026 programme gives you an idea of what to expect: it kicks off with a Meat & Greet party at Club 303, followed by a beach day and a leather night. The Bear Milk underwear party is at Kweens Club, and there's a pool party at Jardín al Bosque, hosted by Anthony (@Cruiseship13). El Purgatorio serves as the late-night bar for the weekend.
US citizens can fly in from the mainland without a passport.
The 2027 edition is set for Thursday 11 to Monday 15 February 2027 (Presidents' Day weekend), according to the schedule on sanjuanbearweekend.com, with tickets through Eventbrite. The schedule page has a couple of day/date typos, so check the organiser's Instagram for the final party line-up.
Where to stay during San Juan Bear Weekend
via Stay22Schedule & Sub-Events
+ Add EventDetailed schedule coming soon.
Check the official website for the latest programme.
Practical Tips
Book Early for Best Prices
Early bird tickets for San Juan Bear Weekend often offer significant discounts. Keep an eye on the organizers' social media for announcements.
Pack for Sun and Fun
Bring swimwear, comfortable party attire, and sunscreen. The event includes beach and pool parties, so be prepared for warm weather and water activities.
Connect with the Community
The event emphasizes community. Engage with fellow attendees at parties and gatherings to make the most of the experience.
Check the Schedule Closely
The weekend features a variety of events at different venues. Consult the official schedule for exact times and locations to plan your participation.
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