This event has ended

Looking for something happening now? Check out upcoming events in Key West.

See upcoming events →
LGBTQ+ Event
Past event

Bear Weekend in

Bears Circuit
Friday, 30 October 2026 · 1:00 PM – 6:00 PM Island House, Key West, United States
5h

About the event

It is Friday of Bear Weekend in Key West, and boy are we having a really good time!! Take a peak at our schedule below to join us for some fun, unique moments!!

Bear Yoga | 1pm to 3pm
Island Mates Manor Pool Deck

Hats & Hoses Pool Party | 2pm to 6pm
Island House

Bad Bear with Cock Shock | 10pm to Late
Saloon 1

To discover Key West Bear Weekend for 2027, be sure to follow them on Instagram!

📸 by Tristan Sutphin
BestGayResortInTheWorld #keywest #bearweekend

Nearby Hotels

via Stay22
Nearby Hotels
Loading map…

Key West, United States Open in Maps →

Our three picks · Key West

via Booking.com
Budget pick
724 Duval Street, Key West

Men-only gay guesthouse above the Bourbon St. Pub on Duval Street, Key West, with a pool and clothing-optional sundeck.

Mid-range pick
1129 Fleming St, Key West, FL 33040

Men-only, clothing-optional gay resort on Fleming Street, a block off Duval, with pool, hot tub, sauna, gym and café.

Last verified: 3 Nov 2026 Source: instagram.com Report an issue

Stay in the Loop

Get the latest LGBTQ+ events and venue openings in your inbox.

Enter your email to receive Pride event updates and new-venue alerts.

Already a subscriber? Unsubscribe

Your privacy choices. We use cookies to run GayOut and, with your consent, measure usage. Learn more