By Tony Adams
In 2026, Island House Key West is celebrating its 50th anniversary with the property and the staff sparkling more than ever!
Island House knows it’s not easy being pretty, but they make it seem that way, delivering an experience that has kept guests happy for five decades. Since opening its doors in 1976, Island House Key West has overcome some difficult challenges–including pandemics, economic and political upheavals, and the growth of tourism–while continuously upgrading its fabulous premises and services to match the high standards of its guests from around the world.
Key West has certainly changed drastically over the past 50 years and over the past two centuries. Its land mass has almost doubled with dredging and infill by the Army Corps of Engineers. Tap water was not possible until 1945 when a pipe from the mainland reached the island. Railways and bridges were a 20th century phenomenon. Its industry changed from fishing to shipwreck salvage to military installations to tourism. Throughout the years, Key West has remained a destination and refuge for gay men, and a place where folks wholeheartedly celebrate diversity even when other communities do not.
General Manager Jeff Smead knows the formula for a successful Island House, saying, “I’ve thought a lot about how a gay men’s clothing-optional resort has needed to grow with the times, especially after 50 years of operation. A lot of people remember visiting Island House during the years when it was really dilapidated, but in 1999 the resort got its first ‘real’ makeover by the owners at the time. Back then, gay men were coming to a summer camp vibe destination, where they could be among their own. Light fare and beer and wine were all that was served in those early days. When the gay community started to become more socially accepted in mainstream society, innkeepers couldn’t rely on simply putting a rainbow sticker on their door anymore, expecting our community to show up. You had to be gay, AND really really good at hospitality in order to earn their business. If Island House was going to compete as an established choice of lodging in Key West, we had to give this property the tools it needed to be successful. During the 2000s, Island House invested in modernized rooms inside our historically old structures, got approved for a full liquor license and restaurant license, and created a 24-hour business model for the bar/café/hotel. It’s what made this place a ‘no-think’ vacation, meaning the time of day or night didn’t matter. We were always open and you could always meet somebody fun.”
Concentrating on improvements to the premises and services did not mean ignoring the rest of Key West. Island House always plays a leading role in the life of the inclusive Key West community. Jeff Smead continues, “We jumped onboard with the special events around the island and played a part in throwing epic pool parties, with every amenity within reach. Island House has more in common with Disney than we do a Marriott, simply because we offer an immersive experience where nuances are perfected daily, and you don’t ever really need to leave the compound for anything. Throw in a local club membership program for local residents to keep the vibe buzzing, and the recipe for success came together. Locals and visitors all in a safe and joyful place, where you get to be the version of yourself you’ve been waiting to meet.”
“I hear it all the time: ‘I’ve been to gay resorts all over the globe, but nothing measures up to what you guys have here at Island House.’ As someone who has been fascinated by gay Key West since my first visit, I can certainly appreciate the ‘feeling’ people are always chasing when they come back,” he says. “Guests may eventually forget that they love our comfortable and welcoming rooms, or our food and drinks, but they won’t forget how it all made them feel, and that’s something I’m very proud of when it comes to both my career and our community.”
How does a clothing-optional gay resort like Island House manage to survive global pandemics including AIDS and COVID? Through careful attention to the needs of its visitors and through strict adherence to health guidelines and mandates. Masks, social distancing, and adjustments to the common areas kept the resort open and safe during much of COVID.
About the challenges of pandemics, Jeff Smead says, “When we at Island House first learned about COVID, it really seemed to be one of those things that wouldn’t affect us here in the United States. Warnings began to hit closer to home, and then suddenly in March of 2020, Florida hotels were ordered to close. It was terrifying and uncharted territory. Many guests were forced to cancel and receive refunds, staff had to leave in order to move back home and care for their families, it was surreal in the worst way possible.
“We were permitted to reopen at low occupancy in early June of 2020. As one can imagine, a place like Island House isn’t really known for social distancing, and amenities like the gym and the video room were off-limits in the best interest of everyone’s health. Our team became leaner, the vibe was certainly different, and we hung on like everyone else was trying to do both emotionally and financially. But after the vaccine was available and the public was allowed to travel safely again, our occupancy honestly exploded. Guys feeling pent up in their homes for so long spurred an absolute frenzy to travel somewhere that ‘felt’ like a foreign country but was still a domestic destination. That honestly was a roller coaster ride that won’t soon be forgotten, with constant 100% occupancy and no end in sight. Operations have normalized over the past couple of years, which made our daily routines feel a lot more comfortable for everyone.”
Visitors often compliment the resort on the high quality of its workers. In a fluctuating economy, both local and national, a skilled, friendly and stable team is not an easy accomplishment, but creating and maintaining that team has been an ongoing priority for Island House. Jeff Smead knows the formula for keeping the Island House family intact, saying, “Our team at Island House is our best asset. We hire locally and always find success when a current employee refers a friend who is ‘perfect for this place.’ We’ve built a team of ‘lifers’ in some cases, meaning guys who are married to this island and will call it home until their dying day.“
“The cost of living in the Keys has certainly been a challenge, so we have to be a place that ‘enlists’ its team as opposed to hiring someone just looking for a pick-up job. Whether a team member identifies as gay or straight, it just doesn’t matter when it comes to their ability to work at a gay resort,” he says. “We’re a tight-knit group of men who take care of each other like family on a remote island. Island House even pays 100% of our full-time employees’ medical insurance, a benefit that is honestly unheard of in any industry, but especially hospitality. It’s an example of how we take care of our own, the way the gay community has always done for themselves well before the world was ready to embrace us.”
“Times have changed” are the opening words to Cole Porter’s song “Anything Goes.” Those words also ring true for Island House celebrating its 50th anniversary in the company of younger men and also those who remember its early days. Dr. Gary Blick, M.D., Founder, and Chief Medical Officer of Ally Wellness, shares his memories both distant and recent. He says, “I discovered Island House in 1980, 46 years ago, when I started medical school at the University of Miami and was 25 years old, having just come out the year prior. I remember being uncomfortable in my own skin and running out of bars, but my Labrador Retrievers and I were welcomed with open arms at Island House. Of course, those days were pre-HIV and I would go down there to have wild sex, and it was Key West at its gayest. As a gay HIV specialist, I have learned how to navigate gay sex! I am now 70 years old, having traveled the world, and it is still the place my husband and I fly to 3-4 times annually, as there is no gay resort that compares, where we can be ourselves, meet great guys from all over the world, eat fabulous food, soak up the warmth and the shade, and play to our hearts’ content together or with new friends. And it never fails that I meet a new patient or two every trip…somebody who may need to know more about PrEP or DoxyPEP.”
Island House is well known for the provision of luxury and comfort, but guests rarely see the courage and care of generations of Island House owners and managers who have made that excellence possible by facing decades of challenges that have beset the island of Key West, the state of Florida, and gay men the world over. The current owner of Island House is Bobi Lore who has a deep sense of history, tradition, and mission. He says, “After I got together with Island House owner, Jon Allen, he came to recognize that I was the person he hoped to find with whom he could entrust his legacy. I’m heartened hearing from so many guests that Jon chose well, as they see the love and care I’ve had for both Island House and the global community that has valued it as a true sanctuary. LGBTQ+ folk are facing strong headwinds these days as there are those in powerful positions who seek to marginalize and even erase us.
As the owner of ‘The Best Gay Resort In The World’ I feel a duty and honor to stand strong representing our community and this sanctuary during these challenging times and beyond. To that I say ‘Long live Island House.’”
We echo that cheer knowing that the current owner, manager and staff of Island House Key West are ready for the next 50 years of fabulous.
