The Oxford dictionary defines a pilgrimage as the “act of journeying through a strange country to a holy place.” Throughout human history people have made their way to sacred sites: Lourdes, Mecca, Dollywood. Last week, I made mine to the Island House. The famed resort permits the fairer sex behind its hallowed doors on only two days each year, during Fantasy Fest and Pride. Since I first learned of the Island House it has existed in my imagination as a place of wild abandon, replete with nudity and very reputable crab cakes. Folks, it did not disappoint.
On Wednesday, the resort played host to myself and a slew of other enthusiastic, neon-clad women. As owner Bobi Lore explains, “Island House has for decades led Key West Pride with our All Welcome Kickoff Party. Proceeds go to assist the business guild which of course assists us and all LGBTQ businesses here. It’s a very symbiotic relationship. We all help each other.”
Lore is a Brooklyn native who has owned the Island House for three years. Lore’s late partner Jon Allen purchased the property in 1999 with the intention of fostering a haven for freedom. In the process he created the most lauded gay men’s guest house in the world.
When I asked what the Island House means to him, Lore noted that the spirit of the place begins with, and belongs to, all those who visit. “It’s more than what it means to me, it’s what it means to a world of people, now including yourself. Anyone who has an open mind and comes here will recognize that it’s a special place. I’ve been tasked with stewarding it and I don’t take that lightly. It’s a sanctuary. It’s a statement to the world.”
It’s a sanctuary Lore is happy to share, on occasion, with us lady folk. “It’s a very welcome chance for us to open our doors to women. There’s no reason why they can’t share in the goodness of this place, the simple fact that it exists.”
During the Pride party, the goodness of the place was in full swing and on full display. The sun was shining, house music was blasting, and a battalion of beautiful men in little more than bow ties and booty shorts passed bottomless glasses of champagne. Asked if this was business as usual for the Island House, one local coolly explained, “It’s usually more sex and less people.”
Keys Weekly’s Reda Wigle goes inside the rainbow during Key West Pride. BRITT MYERS/Keys Weekly 
The Key West Business Guild and Kirby Myers of Kirby’s Closet show their Pride. BRITT MYERS/Keys Weekly 
Now serving…BRITT MYERS/Keys Weekly 
Pete Arnow, Bobi Lore and Rude Girl join the fun at Island House. BRITT MYERS/Keys Weekly 
Miss Gay Pride 2019 mingles at Island House. BRITT MYERS/Keys Weekly
On the condition that I cease recording of any kind, Lore was kind enough to give me a tour of the Island House’s infamous video lounge. Cold as a meat locker and painted red as the devil’s toenails, the lounge welcomes visitors through a corridor of funhouse mirrors into a room with tasteful glory holes, television screens and a sex bench. “This is the multicultural center,” joked one reveler. On Wednesday, in lieu of pornography, the video screens played Island House promotional videos.
This substitution was among the only measures of modesty taken by the resort for the coed event. As Lore explained, “We’re a clothing optional establishment and even during an event like this we intend to stay clothing optional.” As the evening progressed, nudity, for men and women alike, became the favored option, with the pool and dance floor happily awash in bare skin. A veteran of the Island House had some choice wisdom for me and anyone looking to strip down, “Honey, don’t take your shoes off around here — they’ll disappear.”
As the sun set, I made my way home, shoes in hand and glitter everywhere else, having lost nothing but my Island House virginity. Pilgrimage complete, I am grateful to have been a guest where carnality is celebrated and freedom is exalted. As Lore maintains, “There has to be someplace like this, and thank god there is — and when I say god I say it with a small g.” Praise be for Pride with a capital P, and blessed be the Island House.
