By Tony Adams
Island House Key West, is the winner of the 2024 Spartacus Travel Award for Best Gay Resort in the world. For all the thousands of guests who cherish their time at Island House, this is no surprise, but for owner, Bobi Lore, who went to Berlin in March to receive it, the award is a huge source of pride and satisfaction for all the hard work he and his staff have done to renovate the property and perfect the fabulous experience loyal guests of every age have come to expect and appreciate. He says, “It’s my responsibility to make sure that every returning guest finds things even better than their last visit. Improved amenities, food, beverage, and even better staff service if that is possible. I think of Island House like a drafting pencil. I have to keep it sharpened and constantly refreshed. I never let it get dull.”
For gay men, the world has changed considerably since Island House Key West first opened its doors in 1976. Visibility brought victories in equality and legal rights. Darkened windows in gay bars, or funky gayborhoods are less common features these days. Pride celebrations abound, but their sparkle is less often laced with daring and danger. (This is not to say that there are no threats to what has been won, but battles are now more often fought in daylight.) What has remained constant is the need for destinations celebrating who we are as gay men, and that is what Island House Key West continues to deliver luxuriously. A tradition of improvement has been maintained through several changes of ownership and continues into the present. Returning guests will find the place polished and perfected, with cherished essentials securely in place to assure them another great stay.
Listen to James Camp, the first owner of Island House Key West, now living in Daytona, describe for OutClique those earliest days.
“My partner Jim Stokes and I came to Key West having purchased with friends the Key Lodge Hotel. We soon sold our share in that venture and bought an old house on Fleming Street, having decided that we liked living in Key West. One night we were out walking the dog and saw that the “Paul’s Apartments” house was for sale. The property consisted of a private residence built in 1895 on the corner of Fleming and White Streets, and sixteen apartments. Jim was an architect who relished this kind of challenge. During our life together we developed over 30 properties. This one called out to us. We decided to make it into a gay guest house. In those days, Key West was just beginning to be the wildly attractive gay destination that it has become. Only one section of our Island House was clothing optional. Recognizing the need for local gay businesses to band together, I hosted the first meeting of business owners who conceived of the Key West Business Guild. I became its first president.
“One day, we were at the airport collecting visitors when we bumped into a friend from Ohio, Michael Frangella, who was then managing The Marlin Beach Hotel in Fort Lauderdale. On the spot, we offered him a job managing Island House. He accepted our offer and ended up staying with us as Island House manager for six years before moving to San Francisco.
“In 1989, we sold Island House to a couple from Toronto, Jack and Jeff, who continued to refine its concept as exclusively catering to gay men. Our clients had been overwhelmingly gay men, but mixed.
“Jack was a doctor who wanted to make sure that in the event of his death, Jeff would inherit Island House, so he put the property in Jeff’s name. In those days, before same-sex marriage, couples had to go through legal hoops to protect and assure their rights. When Jeff died unexpectedly, the ownership of Island House passed to Jeff’s sister! She ran the operation herself before selling it to Jon Allen and his partner, Martin Kay in 1999.
“When I think back on my years at Island House, my fondest recollections are of my interaction with our amazing guests from around the world. There was no place on the planet like Island House and Key West. I haven’t been back there for many years, but I hear that’s still true.”
At James Camp’s suggestion, Michael Frangella, at home in San Francisco, shared with OutClique his recollections of his years as Island House manager.
“Island House was a joy, and I have fabulous memories of my years in Key West! I was the front desk and reservations manager at the Marlin Beach Hotel in Fort Lauderdale when Jim and Jimmy, whom I had known in Ohio, recruited me to manage Island House. In those days, gay men in Fort Lauderdale used Key West as an escape, as a place to recharge your batteries. You could buy a book of six air tickets for $75 and just go to the airport and jump on a flight whenever you felt like it! My Fort Lauderdale friends thought I was crazy to move there, but Key West was just becoming a gay mecca. When I arrived, they were just building La-te-da [restaurant/bar/cabaret on Duval Street]. There had been a laundromat in the Island House building and there were these huge industrial size driers in one of the rooms. There were sixteen rooms with kitchens and baths. Single Navy men would rent them. There was a family with kids still living in the main section of the house. Jim Camp and Jim Stokes were starting the transformation, with Jim Stokes himself pounding every nail into the deck they built around the pool. Key West had an ordinance prohibiting fences that were more than a certain height, but Island House needed privacy around the pool, so they got a variance by starting the fence measurement at pool deck level.
“Our clients were mostly gay male couples. Even the pool was not clothing optional but in the dark of night, guys would skinny dip. There were no day passes or special events. We had a barbeque grill by the pool on special occasions. We welcomed many young gay men who were just coming out in those carefree days before AIDS. Our very small staff was all gay. I had to pitch in cleaning rooms. Marketing was entirely word of mouth. I convinced the owners to use travel agents as marketers. No computers back then. I had to type by hand every confirmation of each reservation letter! Island House was known as a clean, comfortable, and safe place to stay.
“At first, I had a car which I had parked on the street in front of Island House. I went everywhere on my bicycle. That car never moved. When I went to sell it, I found that vines had crept up the tires and grown into the car! I love it here in San Francisco, but Island House and Key West were pure magic. My friends tell me the resort is even more fabulous today.”
Listen to Bobi Lore pick up the historical narrative from 1999 to the present.
“Jon Allen and Martin Kay had already enjoyed successful business careers when they purchased Island House in 1999. They had a clear plan for the place. They wanted to make it be on par with the kind of luxury resorts they had enjoyed at other vacation destinations, such as Hawaii. Their meticulous efforts succeeded, and they were happy to spend their days managing the resort and enjoying the company of guests from around the world. After Martin passed away at the end of 2013, Jon did not want to remain in Key West. With a friend, he moved to Santa Rosa in the Spring of 2014. That is where we met and began a friendship that grew into a relationship. Jon mentioned that he still owned a guest house in Key West, but he never told me it was the best gay resort in the world! Jon liked to travel, and I had a background in travel services. One of our first trips together was to Key West in 2015, with Jon suggesting that we stay in what he called the Owner’s Suite, room 210 at Island House. I had been to Key West before, but staying at Island House was amazing. I told Jon that he had really created a jewel. I’ve always been very glad he did not sell it after Martin’s passing and I encouraged him never to sell it. He had me walking around the place getting the real guest experience without telling anyone who I was, and then reporting back to him. We kept returning every three months until 2018. Jon came to realize that I was the person he wanted to pass it on to. We were married that April. That idea of having the resort continue as a legacy really mattered a lot to Jon, not just to him but to everyone who loves it and sees it as a home away from home. I realized that I had to take that stewardship seriously. I tend to focus on the good in anything first. So, I noticed how magnificently functional it was; and all encompassing. A guest never has to leave the premises. Food, bar, clothing optional pool – a guest can get it all from one chair poolside, and then a short wander away there are the indoor amenities. I saw that all the ingredients were in place for a clothing optional and sex positive gay resort. I wasn’t going to mess with that. Once I realized that I would eventually be taking over, I wanted to set in stone all those great ingredients. That is the WHAT, but now the HOW is up to me. It’s a lot of work, but I am having a ball doing this, with the help of the best team I could hope to have.I get joy out of seeing guests return, when I hear them say things like ‘I’ve been coming here for 15 or 20 years and Island House is better than ever, and you now have the best staff ever. They make sure my every need is met, and all questions answered.’ That is my favorite feedback.
“When Jon and Martin bought it in 1999 and gutted the place and rebuilt it, they turned it from a guest house into a luxury resort. The motto given was “Island House is now the world’s first five-star gay resort.” That was over 20 years ago. Those rooms were immaculate but barely upgraded, so one of the things I really wanted to do after the pandemic was renovate every single room. I really love seeing that happen. I am so into making the rooms modern, stylish, and fresh. Honestly, we are spending a lot of time and money on this. I would be remiss if I didn’t acknowledge and thank my management team. When I had the opportunity to bring Jeff Smead back and add his husband James Braun to the team, I knew we would succeed. James is very good with tools, design and construction, bringing a crucially important skill set. I knew I had the team I needed to handle redecorating, refurbishing and refreshing – in addition to maintaining the place. I bought a structure nearby and turned it into a furnishings workshop and employee housing. Much of what you see in the rooms is actually made by us right here in Key West. We fabricate all the headboards you see with the built-in lights. We fabricate dividers for the bigger rooms. We repurposed the closets. We rethought the electronics in the rooms. Now the rooms look and feel bigger. We closed down for eight days last September and totally reimagined the bar and the indoor spa area. We are about 30 rooms into the renovation, but our guests don’t know how busy we are because we do most of the work in our new building across the alley.
In addition to being the best gay resort in the world, Island House Key West has become a unique experience for gay men seeking their tribe. Listen to OutClique founder, publisher and editor, Dr. Steven Evans, describe his first time there.
“I made my first trip to Island House about 20 years ago. I went by myself which is how I like to travel, always meeting interesting people. I had packed Barbara Walters’ audiobook (her biography Audition: A Memoir), to listen to poolside. I have been back so many times – I swear I’ve stayed in every room – with the big challenge being how little will I pack this time. All you need are flip flops, swimsuits and tank tops, and most of what you pack will end up going home with you unused.
“I was a church organist in Kentucky when I first went to Island House. The feeling of protection I got when I walked through those doors was amazing. I could finally be myself without fear, and I could drop the weight of feeling inferior, alone, or ‘different.’ I remember thinking that this is what it’s like to feel what straight people feel, to relax at a five-star resort without judgment, guilt, or anxiety. I don’t think I ever realized how heavy the weight of being hidden was until I dropped it when I walked into Island House, because there ain’t no carrying it once you are there. At Island House, I finally was convinced that I wasn’t crazy, that I could be me, and that there were people just like me who found in Island House the one place in the world and the one time in the year when we were all okay. Back home in Kentucky, I would create a specific wall calendar for my Island House trips and start counting down the days. Yes, it meant that much to me (and still does).”
Like owner Bobi Lore, General Manager Jeff Smead and Resort Manager James Braun, take seriously their stewardship of Island House. Jeff speaks for them both when he says, “The reason Island House exists remains the same. Even though the world has changed, the need for a place like Island House is as relevant as it was in 1976. Being a flagship gay resort is at our very core. New/younger guests sometimes arrive with a misconception about the type of place we are, and you can watch after check-in as that expectation is erased, and the light bulb turns on.
“Visiting Island House helps gay men realize how heavy our burden still is today, and this place alleviates that burden you unconsciously carry. What we love showing return guests is that we haven’t changed; we’ve grown. We’ve morphed with the changing times to become this 2024 modern version of Island House. Being stewards of a place like this is a privilege we cherish.
“Neither of us ever expected to be in this position at a gay landmark like Island House. It’s more than just our career, it’s our responsibility. It was somehow meant to be that we are at the helm of something so vital to our community. Island House isn’t just lodging, it’s an experience. And it’s not just a resort, it’s a rite of passage. Jon & Martin left their legacy, and these days with Bobi as the owner, together we’re able to leave our own mark. Reimagining the Island House experience is exactly what we were meant to do. We’re meeting our moment.”
