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Explore Clothing-Optional Key West: Bars, Boats & Boutique Hotels

Clothing-optional Key West
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Key West, Florida is where the dress code is anything from floral shirts and flip-flops to, well, absolutely nothing at all. That’s right! In this sun-soaked slice of paradise, you can sip your margarita at a bar, sail the azure waves, or lounge by the pool in your boutique hotel, all in the buff. It’s where tan lines go to die and the only suit you really need might just be your birthday suit.

With that in mind, Key West invites naturists to embrace the carefree, “no shirt, no shoes, no problems” lifestyle. Whether you’re raising a glass in a local beach bar or catching the sunset on a boat ride, you can bet it’s all about comfort here. And yes, comfort can indeed mean stripping down to the bare essentials under the Florida sun. So, pack light, because in Key West’s clothing-optional bars, boats, and boutique hotels, less is definitely more!

Boutique Hotels

Key West isn’t just for beach lovers and sunset chasers, it’s also for those who prefer their hotel stays to be a little bit more, shall we say, uninhibited. Clothing-optional boutique hotels offer a different way for you to experience this tropical island paradise. Here, the pool rules are simple: swimsuits are optional, sunscreen is not. In other words, it’s all about the personal freedom to enjoy your vacation exactly as you please.

Island House Key West

The Island House Key West  isn’t shy about letting you show your true colors, or perhaps all of them! Nestled in the heart of paradise, this luxury-style, male-only resort invites you to enjoy a relaxed atmosphere where the only required attire might just be a smile. Here, you can lounge by the pool, cocktail in hand, and leave the pants and button-ups for “off-property” adventures. 

We suggest you start your day with breakfast at the 24/7 Cafe & Bar. Then slip into the indoor or outdoor hot tub, work out in the fully-equipped health club, or sit in the steam room or dry sauna to help you sweat out last night’s indulgences. And speaking of indulgences, quench your thirst at the daily happy hour, where you can sip on 4 complimentary drinks of spirits, fine wines, chilled beers, frosty frozen concoctions, or hand-crafted cocktails. With all of these amenities and so much more, it’s no wonder it’s considered “The Best Gay Resort in the World” according to Out Traveler.

New Orleans House

Located above the Bourbon Street Pub on historic Duval Street, the male-only, gay New Orleans House, is in one of the best locations in Key West. You are literally minutes away from some of its most popular attractions like Mallory Square, the Ernest Hemingway House and Museum, and of course, the LGBTQ+ nightlife. Just remember to put some clothes on before heading out.

Mornings start with a continental breakfast, perfect for fueling a day of exploring or simply lounging poolside. Feeling ambitious? Then a workout at the on-site fitness center is a must, followed by a relaxing soak in the jacuzzi. As evening rolls around, the complimentary happy hour, where good intentions come to die, is your prelude to a night-time of indulgences. The on-site Chicken Shack keeps bellies full with American eats, while venturing a bit further, the Bourbon Street Pub and its “boys” are waiting to escort you in to wash down the day’s adventures and enjoy a night of whatever you want it to be. 

Equator Resort

While shirts and shoes, among other things, are optional, at the Equator Resort, good times are a must. This all-male, clothing-optional hideaway, just three blocks from Duval Street is an escape from the usual touristy stays and lets you delve into a more, need we say, exclusive experience. We’re talking less ‘lost luggage’ and more ‘lost in paradise’ as you step into this laid-back, post-modern Caribbean oasis.

You can pick your pleasure from a variety of rooms. Choose to wake up to island vibes, poolside views from your own private balcony, or go big in the private owner’s suite. All come with the essential private bath for solo splash time. Plus, each room comes with not one, not two, but nine complimentary adult male channels, so there’s always something on TV to keep you entertained. With both a complimentary Continental breakfast and daily happy hour, the Equator Resort is your ticket to an unforgettable Key West experience.

Clothing-Optional Tanning Decks

Tired of tan lines? On Key West’s Key West’s clothing-optional tanning decks, you can choose to lose the swimsuit and embrace the sun in all your glory. Just be sure to slather on the sunscreen. Because while modesty might not be mandatory, protection from the Florida sun certainly is. 

La Te Da

At the La Te Da, the clothing-optional tanning deck is where inhibitions and swimwear often take a flying leap off the deep end. Perched like a sun-lover’s crow’s nest atop the hotel, you have the chance to work on your tan, and perhaps your nerve. It’s where the phrase “full coverage” only applies to the SPF of your sunscreen. And , don’t forget your sunglasses … for eye protection, of course!

Heron House

Ditch the layers and embrace the rays on the Heron House‘s clothing-optional tanning deck. Here, you can strip down to your birthday suit and bronze every nook and cranny under the forgiving Florida sun. The Heron House deck is a judgment-free zone where the only thing you need to wear is sunscreen and a smile. It’s the perfect place to tan like a pro, without ever having to worry about tan lines.

Alexander’s Guesthouse

A retreat for the soul, Alexander’s Guest House is an LGBTQIA+ adult-only guesthouse in a restored three-story, conch-style house dating back to the early 1900s. Here, there’s not one, but two clothing-optional tanning decks where you can strip down to your birthday suit and let the sun work its magic, so no pesky tan lines dare interrupt your vacation glow.

Clothing-Optional Bars

Bourbon Street Bar

Bourbon Street Bar is Key West’s premier video music bar, with the biggest TV screen on the island. As the clock strikes 10:00 nightly, the Men of Bourbon turn up the heat with bar-top go-go dancing and R-Rated thrills. But wait, there’s more! Venture out back to the outdoor theater, tiki bar, and pool area, a.k.a the clothing-optional Garden Bar, for a little “adult entertainment” where pretty much anything goes.

Garden of Eden

There are lots of rooftop bars in Key West, but The Garden of Eden, perched atop the Bull and Whistle Bar on Duval Street, isn’t your average rooftop bar. As the sun sets and the night heats up, it’s about feeling the music, and maybe less of your clothes. Here, you can strip down to your comfort level and groove to the rhythms of the night, where the dress code is optional and the vibe is always uninhibited. 

Clothing-Optional Boat Charters

Clothing-optional boat charters invite you to cast off more than just your everyday cares. Here, even swimsuits are optional! As you sail through the sparkling waters, you can soak up the sun in the ultimate state of freedom, feeling the ocean breeze as nature intended. These adventures are a chance to embrace the open sea without the constraints of clothing, providing a refreshing twist on traditional boating.

Toon Time Charters

Set sail on the “Toon Time” with Toon Time Charters where clothing is strictly optional, and the vibes are always chill. Deck out in full regalia or embrace your nakedness. This adults-only charter limits its crew to six fun-loving souls, creating a laid-back, “anything goes” atmosphere, as long as everyone is having fun. Feel free to bring along adult beverages, but leave the hard stuff at home. Just pack a towel, hat, and shades, and remember, while you can leave your swimsuit behind, some clothing is required around the marina 

Fish N’ Chicks

Strip down to the basics and set sail with Fish N’Chicks Key West Charters where the dress code is optional. Embrace the freedom of clothing-optional boating charters where you’re free to soak up the sun as nature intended. Hop aboard with up to six people and find all of the essentials: sun lounges, a well-stocked cooler, and even snorkeling and paddleboarding gear. Make memories that last long after the tan fades.

Blu Q Catamaran

Feel the Key West sunshine warm your skin as you relax on the spacious deck of the Blu Q Catamaran, for an all-male gay charter sailing the high seas. Here, you can embrace complete comfort, so feel free to shed your worries and your clothes. Want to cool off? Take a dip in the crystal clear water or go snorkeling or kayaking. All gear, snacks, and water are included on this all-day charter. It’s the perfect opportunity to meet new guys and make some great memories.

Clothing-Optional Key West: Sun, Fun & Freedom

Key West’s laid-back lifestyle and island vibe are the perfect mix for naturists to escape the confines of everyday attire and societal norms. Openness and acceptance shine brightly here. It’s become a state of mind where sun, fun, and freedom play out in tropical harmony. So, leave your inhibitions (and your overpacked suitcase) at home, come as you are, and discover why clothing-optional Key West is your perfect island getaway.

For more Key West, check out our LGBTQ+ Travel Guide to Key West.


**Disclaimer: There is a good chance that this post contains affiliate or sponsor links. If you make a purchase through them, we may receive a small commission at no extra cost to you (for which we are extremely grateful).

Also, while we do our best to highlight LGBTQ-friendly destinations and businesses, info provided is based solely on personal experience and recommendations by community partners. We hope that nobody experiences discrimination or homophobia while visiting Florida and beyond, but we make no guarantees. Please inform us if you experience discrimination or homophobia while visiting any destination so we can make updates to our recommendations.

Events are subject to change. Please check the events webpage for updates and schedules.

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