Plus, the convenience of dinner, coffee or a party just a step outside my door felt like an additional layer of luxury. My initial concern about late-night noise keeping me awake proved unfounded (though the luxe, feather-topped bed probably helped). Room 106 would be my Island House base of operations (and subject of poolside gossip). That’s where they host the lively Sunday and Wednesday pool parties, and it’s right beside the resort’s delicious, 24-hour bar and café. He led me to my room beside the heated pool, the epicenter of Island House activity. (Plus, when they’re not on the frontlines of the resort’s COVID response, they’re great sources of gossip as you get the lay of the land.) The friendly staff at Island House is one of its greatest assets, and this is a great way to get to know the faces you’ll see as you traipse around the grounds in a towel or less. Even though this was my third visit to the Island House, I always opt for a quick refresher tour when I arrive. The always cheery front-desk clerk told me the room was ready early, but I decided to delay settling in just yet. I arrived before check-in and planned to stash my bag and hit the pool right away.
However, if you’re not up to much exploration, Island House is the perfect one-stop spot for the best, gayest vacation you can get. Nestled in Old Town, the resort feels comfortably isolated once inside the grounds, but is just a quick walk to most areas of interest on the island. The local queer community is woven into the DNA of the island, from politics to business leaders and artists, but the central hub for gay life in Key West is Island House. It’s on display with the drag queens down Duval, at the annual Fantasy Fest and even in City Hall, where they proudly installed Florida’s first openly-lesbian mayor, Teri Johnston. The island embraces uniqueness with its more-than-a-marketing-tagline “Close to perfect, far from normal” ethos. Walking across the tarmac (there are no jetways), you see a replica of the southernmost point landmark and large figurines that look right out of Squid Game under the words “Welcome to the Conch Republic.” It’s a cheeky nod to the island’s brief (mostly performative) cessation from the nation, but it’s also an enduring reminder of Key West’s proud independent spirit and uncompromising weirdness. The island’s tiny airport is the first indicator to visitors they’ve left the drudgery of their origins behind for something different. If you think you’d enjoy a gay getaway at a top-rated clothing-optional resort for men, reserve for your choice of dates as soon as possibleĪ short, direct flight from NYC got me into town early one Monday morning. We appreciate the Island House as a Towleroad sponsor and thank them for the financial support for this special coverage of the resort.