Get Ready for Fur, Fun, and Florida Sunshine
October 29 – November 2, 2025
By OutClique writer
As fall approaches to cool down the summer, things are heating up in paradise. Key West Bear Weekend returns October 29 to November 2, 2025, inviting bears, cubs, otters, admirers, and allies to soak up five days of sun-drenched celebration in one of the most LGBTQ+ inclusive destinations in the world.
Equal parts laid-back vacation and vibrant community gathering, this tropical event blends poolside parties, island adventures, and unforgettable nightlife with a warm, welcoming vibe that makes everyone feel at home. I had the pleasure of chatting with Robin Gray, one of the masterminds behind the weekend, to talk about the origin story, what’s new for 2025, and why this Key West tradition is more than just a party… It’s a movement.
OutClique: For those new to the event, can you share the origin story of Key West Bear Weekend and how it’s evolved over the years?
Robin Gray: Key West Bear Weekend began in 2017 with an invite by Jeff Smead at Island House Resort. We had been working with Jeff and Island House through our publication Bear World Magazine, and in a meeting with him he asked if we’d consider starting a bear weekend in Key West. We leapt at the opportunity and invited our friend Shane Tate on board to help guide the development and running of the weekend as he had been a very successful bear event organizer and promoter in New York City, running various bear nights as well as the new Fire Island Bear Weekend.
The first event in 2017 saw us having to run the event a mere 6 weeks after Hurricane Irma had ripped through the Keys, causing a huge amount of devastation. But the community rallied and the attendees were thrilled to be able to come and celebrate with us.
Over the years, the numbers steadily grew up to the pandemic where we had to put the event on hold for two years to keep our community safe. Following that, regular attendees and newbies loved being able to get back to Key West and we’ve been growing steadily again ever since.
OutClique: What makes Key West the perfect destination for a bear weekend and how does the city embrace the event?
Robin Gray: Key West is a slice of Caribbean paradise where everyone can party in the crystal clear waters and tropical climate without having to leave the US. The island is closer to Cuba than it is the mainland and operates with such a relaxed vibe. When you arrive on the island you can feel all your worries and stresses just disappear as the pace of life slows down and the frozen cocktails feel so good enjoyed in a pool!
Key West is widely recognized as a welcoming and inclusive destination for LGBTQ+ travelers, known for its vibrant gay scene and rich history. It’s a place where people feel comfortable being themselves and where diversity is celebrated, with the city’s motto One Human Family being testament to that.
The wide variety of LGBTQ+ bars, restaurants and hotels have all rallied behind Key West Bear Weekend as they really value the bear community and the way we respectfully engage with our hosts, as well as being the part of the LGBTQ+ community who eats and drinks a lot while we vacation!
OutClique: What can attendees expect from the 2025 Key West Bear Weekend? Any new venues, parties, or surprises on the horizon?
Robin Gray: Every year we try to add something new to the schedule while also maintaining some of the regular events that people have come to know and love.
We have a new party this year we’re calling our Jocktober party held at the famous Bourbon St Pub on Duval Street. In the warm sweaty Key West nights, there’s nothing better than being able to drink and dance in just a jock, so we’re fully embracing that with this party where it’s strictly jockstraps only! Plus, we’ve added in a new fun feature that will please the underwear kinksters amongst us all with the used jock swap service. This will see our host, Puddin’ Tain, and our sexy gogo bear, Ner, help the bears trade their jockstraps with other willing participants. Let the fur fly!
OutClique: How do you balance the mix of social events, nightlife, and daytime activities to cater to both newcomers and longtime attendees?
Robin Gray: People are attracted to Key West Bear Weekend because we’ve established our event as being a more chilled out alternative to some other bear weekends. It’s also got a great reputation as one of the friendliest too. We have smaller numbers so it’s a less intense option for those who are seeking to relax and meet some new friends in a chilled out environment. So while we’re always keen to make sure people have hot nights, we make sure that our daytime activities are less intense and people have time to truly enjoy their vacation time with us.
We always throw in one daytime activity that acts as a welcome event to Key West too, so if you’re new there’s a way to get out and explore the island. A couple of years ago it was a key lime pie crawl where attendees got to taste the famous key lime pie in a variety of destinations, but this year it’s a rum and cigar tasting trip where we head to two venues in the Old Town to explore how Caribbean rum and cigars are made.
There’s also an element of self-guided exploration that is encouraged too. Key West is a small island that’s very easy to navigate on foot, by bike, by cab or even via the loop bus that links a lot of major destinations. Our Key West Bear Weekend All Access Pass offers discounts at local bars, restaurants and shops across all five days so people can get out and explore these great places in their own time and with a budget in mind.
OutClique: Can you tell us more about this year’s theme or overall vibe and what kind of experiences guests can look forward to?
Robin Gray: One of the fun things about Key West Bear Weekend is that we usually sit across Halloween somewhere within our five day schedule, so that is a big vibe for some of the weekend. This year, Halloween is on Friday which is our fetish and gear night at Saloon 1, so we’re having a Halloween gear party! Think butch leather daddy grim reapers and ghosts in harnesses!
But, overall, Key West itself brings the vibe… that chilled out feeling that the island has and is so unique to Key West with the friendly locals and relaxed environment, that is the vibe that we embrace wholeheartedly.
OutClique: Are there any charitable or community-focused elements tied into the weekend that you’d like to highlight?
Robin Gray: Yes, our Saturday night party is always a charity ball which supports the local LGBTQ+ non-profit Queer Keys with their vitally important work. This year’s theme is Pirates of Men’s Pants, which as you can imagine is pirate-themed! The Keys are famous for their pirate history with Blackbeard himself known to plunder ships around the Keys as they sat on important shipping routes back in the day. The area is also home to a lot of treacherous waters which has led to a number of shipwrecks and there’s a variety of museums and attractions about pirates. So we invite everyone to grab their poppers of eight and come along to plunder each other’s booty as we raise money for Queer Keys with a donation from every cover charge.
OutClique: What advice do you have for first-time attendees who might feel nervous or unsure about joining a bear weekend?
Robin Gray: We have a reputation for being one of the friendliest bear weekends in the world, and for good reason. Our smaller numbers make this weekend so much easier for people who maybe struggle with larger crowds and also really helps in developing meaningful friendships. Our host hotel, Island House Resort, is world renowned, not only for its facilities and food & drink, but also for the friendliness of their staff. Jeff and James have curated a resort where everyone is made to feel welcome and you can engage in as much or as little as you want. The resort is clothing optional and there is the famous Red Room playspace, but do you HAVE to be naked and play all the time? NO! There are many of our attendees who just want to enjoy being amongst their own community and chilling out around the pool with the award winning food and cocktails!
OutClique: You’ve also recently launched a second bear event in Key West in the Spring, why did you want to launch something new?
Robin Gray: Key West Bear Weekend has the friendly and chilled reputation down. Yes, our evenings do have a sexy edge to them, but it’s a lot of friendly fun first and foremost. However, we felt like there was an opportunity to embrace a bit more of the frisky fun that Key West is also known for. There are many other events in Key West catering to other parts of the community where sex and kink are front and center, so why can’t the bears have some of that too?! That’s where WOOF Week comes in!
WOOF Week was originally a concept driven by Island House in 2024 and given our huge success with Key West Bear Weekend, they invited us to collaborate from 2025 onwards, and we were very happy to accept!
WOOF Week includes hanky parties, sex parties, naked nights, pornstar hosts and a headline party with a major international DJ, so if you’re more inclined towards that level of fun and furry hedonism, then look out for the info on WOOF Week 2026 (April 21 – 26) dropping later this year.
Get your rooms booked at Island House as they sell out fast! Plus, our super early bird passes for WOOF Week are currently on sale at the cheapest price they will ever be, so if you want to come and have some sexy, furry fun in paradise with pornstars and international DJs, visit www.tickettailor.com/events/grayjonesmedialtd
OutClique: As you look toward the future, how do you envision Key West Bear Weekend and WOOF Week continuing to grow or evolve in the coming years?
Robin Gray: We have the ambition to grow these events in scale so as many bears as possible can come and explore what the beautiful Key West has to offer. We also will continue to expand how we work with local hotels, shops, restaurants and bars so they too will financially benefit from this increase in numbers to the island. We’ve been passionate from year one that we want to make sure that everyone is encouraged to get out around the island and make the most of the thriving local business scene, which is why wristband passes for both events afford people discounts at local shops, restaurants and bars.
We are already starting to onboard new hotel partners for both events which will lead to a much bigger capacity for the event and, of course, the new concourse at Key West airport has opened which will lead to new flight routes opening up into Key West providing direct and cheaper flight options.
Bigger numbers, bigger schedule, more diversity of events, greater involvement with our local friends and businesses, and more beary bums in hotels! That’s the way we intend to grow, but all the while ensuring we don’t lose our friendly, welcoming and inclusive identity.
OutClique: Lastly, how do people keep up with all the latest news about Key West Bear Weekend and WOOF Week?
You can follow us on social media, we’re on Facebook @Key West Bears, Instagram @keywestbears, and BlueSky @keywestbears – here’s our Linktree: https://linktr.ee/keywestbears
For Key West Bear Weekend, head to KeyWestBearWeekend.com for all the info, and you can sign up for our newsletter there which will get you all the updates first for both Key West Bear Weekend and WOOF Week.
WOOF Week has a new landing page dropping later this year with the exciting schedule for the 2026 event.
OutClique: Robin, thank you so much for taking the time to enlighten me and our readers about Key West Bear Weekend and what’s to come!
Whether you’re drawn by the sunshine, the sexy fun, the sense of community or all of the above, Key West Bear Weekend is the ultimate escape for anyone craving connection, celebration, and a little fur in the Florida heat. With fresh parties, island flavor, and inclusive energy at every turn, the 2025 edition is shaping up to be the biggest (and beariest) yet.
Don’t miss your chance to be part of it. For tickets, accommodations, and event details, visit KeyWestBearWeekend.com and follow @keywestbears on social media. For even more wild adventures, keep an eye out for WOOF Week in April 2026.
Pack your sass, your jockstraps, and your sense of adventure, Key West Bear Weekend is more than calling… it’s roaring.
