San Juan Bear Weekend Returns for Second Annual Celebration in Puerto Rico, February 2026

San Juan Bear Weekend 2026 marks the second annual outing for this vibrant gathering tailored to the bear community, running from Thursday, February 12, to Monday, February 16, 2026, in San Juan, Puerto Rico. Hundreds of attendees, described as "sexy bears" from around the world, are expected to escape winter chills for a five-day, four-night experience blending tropical relaxation and energetic nightlife. The event is organized by BEAR MILK NYC , which curates a schedule of beach gatherings, pool parties, open bars, and takeovers at local gay venues.

This edition builds on the success of the inaugural event, emphasizing community connection in an inclusive environment for bears and their allies. Puerto Rico's "La Isla del Encanto" serves as the ideal backdrop, with its stunning beaches and welcoming LGBTQ+ scene in San Juan. Attendees can purchase All Access Weekend Passes for entry to all major events, with early bird pricing available until December 15, 2025. Tickets and full schedules are accessible at SanJuanBearWeekend.com .

Daytime programming focuses on leisurely pursuits under the Caribbean sun. Organized beach and pool parties provide spaces for mingling, tanning, and enjoying crystal-clear waters along San Juan's shores. These gatherings foster a relaxed atmosphere where participants can connect with fellow bears in a supportive setting.

Puerto Rico's vibrant culture enhances the experience, with opportunities to explore natural beauty beyond the parties. Organizers highlight the island's appeal as a mid-February escape from colder climates elsewhere. Hotel recommendations and travel tips are provided on the official website to help attendees plan their stays.

As night falls, the event shifts to San Juan's renowned gay nightlife. Exclusive parties at local venues form the core of evening entertainment, featuring music, dancing, and drinks. A highlight is the takeover of El Purgatorio, San Juan's dedicated bear bar, where hundreds of bears will gather for themed nights planned by BEAR MILK NYC. These events span the full four days plus the extended weekend, ensuring non-stop fun.

The lineup includes selections from San Juan's gay bar scene, promoting an inclusive celebration of bear culture. Organizers encourage following social channels for real-time updates on venues and themes .

San Juan Bear Weekend underscores the growing visibility of bear events in the Caribbean, drawing a global crowd to Puerto Rico's affirming LGBTQ+ destinations. By centering bears—a subgroup within the broader LGBTQ+ community—the event promotes body positivity, camaraderie, and shared experiences. Participants report forming lifelong friendships in this welcoming paradise.

The second annual return signals strong demand, with early booking urged due to limited tickets. Refunds follow Eventbrite policies, and the in-person format starts at 7:00 PM GMT-3 on February 12. This gathering not only boosts local tourism but also strengthens international ties within the bear community.

For those seeking a sun-soaked break, San Juan Bear Weekend offers a curated path to paradise, open to all who embrace its spirit. Visit SanJuanBearWeekend.com for details.