Strip or Just Tease? Key West’s Famous, and Infamous, Clothing-Optional Gay Guesthouses

C'mon in as we share what it's really like to stay at a clothing-optional gay guesthouse, saving you an exhausting online search for candor on what may seem more daunting, or less appealing, than it really is. In this episode, Gay Key West Uncovered shares an honest glimpse into what awaits you, whether you're seeking debauchery, whatever that looks like to you, or a quieter stay.

Join us on another journey through the compact paradise of Key West, where traversing from end to end is a breeze, but the options are plentiful. Along charming Fleming Street in Old Town, you'll find two exclusively male clothing-optional guesthouses and one eclectic mixed-gender inn, all conveniently clustered within a few blocks of each other.

Of the two, Island House is the better known. A private club renowned for its openness towards sexuality, but also its exceptional amenities including a great restaurant, luxurious bedding, sun-drenched decks, adult playrooms and a fully equipped gym. They throw a daily happy hour and weekly pool extravaganza, overseen by the manager, the de facto Dolly Levi of Key West and his husband.

Equator Resort has a more laid-back atmosphere emphasis on racial diversity and very friendly poolside gatherings. It's the ideal spot to unwind, whether you're lounging with a book or engaging in a spirited game of naked “chicken.” Favored by many return visitors, from our experience, this is also where a lot of hesitant Midwestern boys dip their toes in the water before warming up to the climate, if that sounds at all appealing.

Nestled between these bare-it-all hotspots lies Alexanders Guesthouse, a refined retreat that warmly welcomes all guests, regardless of gender or gender-identity. With its beautiful Conch-style architecture and sumptuous breakfast spreads, it offers a quieter and comfortable alternative. Plus, it still offers male-only, clothing-optional upper sundecks if tan lines aren't your thing.

Venturing to Duval Street, New Orleans House steals the spotlight with its lively naked volleyball matches, backyard bar and pulsating entertainment. While the atmosphere may be raucous, it's all in good fun—just slip on a pair of shorts when venturing back into public view.

What these guesthouses have in common is that they all are whatever you want them to be, as long as you want them to be gay. Clothing-optional means just that, and plenty of people are dressed. Whether you're naked or not, they are still forever queer and incredibly liberating. And even relaxing, if that's what you want.

Gay Key West Uncovered is a six-part miniseries podcast that is unapologetically queer, and not-so-straight from the mouths of drag queens, creative digital nomads, the fiercest lesbian boat captain you should have the pleasure of meeting, naked pool boys, business owners and even the mayor. This time we're most interested in the naked pool boys, and what it's like for them to welcome guests who've left their swimsuits up north. Listen to our second episode here, and join host Bobby Hankinson and Towleroad as we answer your questions about clothing-optional guesthouses in Key West in the gayest way possible: