Gay Guide to Key West
TimurDC’s Guide for Where to Stay, Eat, Play and Be Mary 💃
Courtesy of OurKeyWest
It may come as no surprise that Key West, Florida, is one of the most gay-friendly destinations in the US. After all, the charming island was literally the furthest place away from society of the original 13 colonies. Just like P-town and San Francisco find themselves at the fringe of our continent, Key West’s little corner of Caribbean Florida is filled with history, charm, whimsy, and mischief — the perfect recipe for a gay getaway destination. As the season begins to change, much of the country is entering #SweaterWeather while us Floridians enter what we call “Season.” This unique time of the year is when all of you migratory men flock down to our sunny shores, glistening coastlines, and forever summer vibes. This Season, I have the essential guide to Gay Key West — where to stay, eat, play, and be merry, Mary 😜. Whether you’re looking for a romantic family getaway for the holidays, or to stuff your stocking with merry men, our comprehensive guide rates your potential experiences from mild, spicy, and hot … who doesn’t like a little holiday spice?
STAY:
The Alexander House [mild]:
Courtesy of The Alexander House
The Alexander House is an LGBTQA guesthouse which means all humans are welcome, of course, but they also hold an especially safe space for members of the Lesbian, Gay, Bi, Trans & Queer groups. They welcome all Allies as well. The resort is packed with communal amenities like a lovely pool, refreshing hot tub, and elegantly designed guest rooms (pro-tip: request the penthouse, it’s a charming apartment with a full kitchen and view of the entire resort and neighborhood). The resort is clothing optional only on their rooftop patio. As the resort is fully inclusive of the LGBT and ally spectrum, certain male-focused activities are most appropriate in the privacy of your guest room. Fortunately, this Historic B&B is directly across from Key West’s famous Island House [rated hot], which offers food, friends, fun, and friskiness [read below for more information]. Breakfast, snacks, and happy hour are served daily, offering quite the tasty spread of your daily essentials.
The resort is ideal for a more mellow, luxurious, and communal getaway experience.
1118 Fleming St,
Key West, Florida 33040
info@alexanderskeywest.com
The Equator Resort [spicy]:
Courtesy of The Equator Resort
The Equator Resort believes all the typical male-only resort expectations can be met without sacrificing class or service. Imagine a domestic tropical location where the locals and visitors alike embrace an open to all concept of thinking. A place where the official adopted the philosophy of the city is “One Human Family”.
Now complete that with an all-male, clothing-optional environment that prides itself on guest privacy and comfort. Tucked away in the heart of Old Town Key West, the Equator Resort is just 3 blocks from Historic Duval St. Providing easy access to a city filled with history, culture, festivity, and most of all relaxation.
The resort offers a large, lush, and open private setting with 2 heated pools and two hot tubs. Comprised of 5 historic properties each room is unique and offers its own charm all with private baths and spaciousness. Each guest room has 11 NSFW channels with a variety of adult entertainment streaming at all hours. The daily happy hours are often sprinkled with pants-off activities, and there is really nothing better than a late-night hot tub gathering with your housemates and locals.
The resort is accessible for guests only (and whomever they bring) and is not open to the public. This type of exclusivity makes each visit to The Equator Resort feel like you’re going to a gay sleep-away camp, making an intimate environment to make friends, have fun, and your other favorite F-words outside, inside, in the pool, or wherever you’d like. The resort is just blocks away from the Harbor and Duval Street — two essential areas for recreation, shopping, partying, and food.
822 Fleming St,
Key West, FL 33040
info@equatorresort.com
The Island House [hot]:
Courtesy of The Island House Resort
Located in historic Key West, across the street from The Alexander House and just blocks away from The Equator Resort and Duval Street, The Island House is a 34-room boutique hotel created exclusively for gay men. This all-male, clothing-optional resort is the most amenity rich of the three within this guide. It is important to note this venue is open to the public (day passes are available for purchase), which gives visitors access to the House’s complete gym, sauna, steam room, hot tubs, multiple sunning decks, dark room, pool, restaurant/bar, and of course, the ample men staying at the resort. The outdoor pool and hot tub are surrounded by lounge chairs, tropical greenery, and an outdoor massage cabana adjacent to group activities yet private enough for the perfect male-on-male treatment. The daily happy hour is seemingly all-day, with pool party vibes attracting gays of every color, tribe, age, and origin. The entire hotel (except the gym) is clothing optional and the staff plans on- and off-site activities specifically for gay men.
The guest rooms are design-minded, just big enough for a Key West crash-pad, streaming NSFW content on screens, and are very inviting for any leaving-the-door-ajar activities. This venue is perfect for cruising, relaxing, partying, playing, sunning, and having a 100% gay vacation.
1129 Fleming St,
Key West, FL 33040
https://islandhousekeywest.com
reservations@islandhousekeywest.com
EAT:
Date & Thyme [mild]:
Courtesy of Date & Thyme
If you are looking for a health-forward, organic, specialty diet (vegan, gluten-free, dairy-free, etc.) and natural food and drink options, within an LGBT-owned and operated venue, the charming Date & Thyme market-meets-restaurant is the spot for you. It is perfect for a pre or post-workout smoothie, morning coffee on a sunny patio, and of course salad, sandwiches, bowls, and other delicious natural foods. Honestly, anything you select here is so delicious, you’ll likely end up here again. Their menu offers the freshest healthy options, with super-food smoothies and a variety of açai bowls, plus more substantial wraps and sandwiches. The market is located directly across the street from The Equator Resort, a few blocks from Alexander and Island Houses, and two blocks from the harbor. Year after year, I keep coming back for more healthy freshness!
829 Fleming St,
Key West, FL 33040
Mangia Mangia [spicy]:
Courtesy of Mangia Mangia
In Key West, Mangia Mangia is famous not only for its fresh homemade pasta but also for creating a nourishing meal that envelops you by sight, smell and taste. Choose from spaghetti topped with green-lipped New Zealand mussels in a garlicky marinara sauce, Linguine with clams in shallot, white wine, garlic, and butter broth, and a delicious variety of other pasta dishes. Dig into the simple, full flavors while you keep one eye on the locals walking their dogs, meeting on the corner to swap stories of the day, or chaining up their bikes to come inside and join you. This Key West establishment is gay-owned and operated, iconic for its family-style meals, and is the perfect setting for a family date night or post-weekend recovery meal … if you’re going to carbo-load, you may as well enjoy the finest flavors of Italia.
Mangia Mangia is on the corner of Southard and Margaret right smack dab in the heart of the neighborhood Old Town, Key West, just steps away from The Alexander House, Island House, and Equator Resort.
900 Southard St,
Key West, FL 33040
Hot Tin Roof [hot]:
Courtesy of Hot Tin Roof
Tennessee Williams’ most famous play, Cat on a Hot Tin Roof, is the inspiration for Ocean Key Resort & Spa’s signature restaurant and namesake, Hot Tine Roof. Their menu is prepared in a unique culinary style dubbed conch-fusion, a mélange of tastes from Florida and the Caribbean creating the unique ‘Floribbean’ flavor. Hot Tin Roof offers a gorgeous dining room and verandah starring a spectacular sunset view over the harbor. Detailed teak woodwork and a hand-painted ceiling bring a warm and romantic glow to this beautiful space. Hot Tin Roof is very popular for couples, families, groups, and sunset seekers, and we highly recommend making reservations to snag your perfect seat. Inside you’ll enjoy hand-painted murals by local artists. The décor is second only to the stunning view of the ocean and the Sunset Pier, just steps away. Whether you prefer surf, turf, or both, every dish we enjoyed was memorable, well-plated, and delicious!
0 Duval St,
Key West, FL 33040
https://www.oceankey.com/key-west-restaurant/
PLAY:
La Te Da [mild]:
Courtesy of La Te Da
La Te Da is a Key West landmark with 15 guest rooms, a piano bar, a terrace bar, and a cabaret. This iconic LGBTQ+ venue is located right on Duval Street in the middle of all things nightlife. They offer some of the best live entertainment on the island, including Key West legends, Christopher Peterson’s Eyecons drag show, and Randy Roberts’ cabaret! These seated shows happen numerous times weekly and are the perfect activity to kick off your long weekend and stay in Key West. In addition, to live entertainment, La Te Da offers a tropical open-air fine dining in a casual atmosphere and a Sunday Tea that brings the queers, gays, queens, ladies, and daddies alike. Any day or night of the week, La Te Da offers a hospitable environment for food, fun, and friends.
1125 Duval St,
Key West, FL 33040
801 Bourbon Bar & One Saloon [spicy]:
Courtesy of 801 Bourbon Bar
Located in the heart of the Key West “gayborhood” on Duval Street, adorned by rainbow-paved crosswalks, you will find 801 Bourbon Bar and its raunchier counterpart, One Saloon. This gay bar is known for its nightly drag shows featuring the World Famous 801 Girls at 9 and 11 PM, karaoke every Sunday afternoon starting at 4 PM, and upstairs cabaret and bar. It’s super friendly for any novice gay bargoer. If you are looking to turn the temperature up, sneak through their back door to enjoy the clothing-optional gay leather bar, One Saloon, where NSFW content is streaming on TVs (the only light in the venue), a male-only back patio room where anything goes, and their famous sling to strap yourself, your partner, or new friend in for a ride. However you’d like your night to go, 801 Bourbon Bar & One Saloon has a flavor right for you.
801 Duval St,
Key West, FL 33040
The Bourbon Street Pub [hot]:
Courtesy of The Bourbon St. Pub
The Bourbon St. Pub is globally recognized for its go-go dancers known as the Hot Men and Boys. Enter this multi-roomed gay bar to be immediately greeted by some of the hottest men and boys from all over the world performing for you. You can catch them nightly on top of the bar for your viewing pleasure, starting at 10 PM. Private lap dances are available, for those up close and personal moments. The Bourbon St. Pub occasionally has some of the sexiest and hottest porn stars with special shows to get your blood pumping!
Continue past the numerous platforms and stage to the male-only outdoor patio for even more wild fun. There you will find a full-service bar, clothing-optional pool, hot tub, raunchy roof deck, and a hidden jungle garden perfect for cruising and adult play. The Bourbon Street Pub is a part of the New Orleans House, another guesthouse to stay
Pro Tip: when visiting during the holidays, this property is best known for its ruby slipper drop during NYE at midnight — the entire block becomes a street party to usher in the new year.
724 Duval St,
Key West, FL 33040
BE MERRY, MARY:
Key West Garden Club [mild]:
Courtesy of The Key West Garden Club
The Key West Garden Club at West Martello Tower is a tropical garden paradise by the sea on the site of a former Civil War fort. It has garden rooms to delight you, history to intrigue you, and the beach and sea to inspire you.
Open to the public, it is maintained by member volunteers of the Garden Club. It is a non-profit organization with a mission to provide the community with educational opportunities related to tropical gardening and to the West Martello Tower, a National Historic site where the Club is located.
This romantic destination is a wonderful example of the botanical history of the island, is ideal for a romantic moment, some personal space, group outings, and even private events (did someone say anniversary party?!).
Pro-Tip: head towards this park for the best fireworks view on holidays like July 4th!
1100 Atlantic Blvd,
Key West, FL 33040
Key West Tropical Forest and Botanical Garden [spicy]:
Courtesy of The Key West Tropical Forest and Botanical Gardens
The Key West Tropical Forest and Botanical Gardens are the only “frost-free,” subtropical forest and botanical garden in the continental United States. A tropical environment with ample rain allows most trees to retain their leaves in the dry season (December through late May). It is home to endangered and threatened flora and fauna. Unlike traditional botanical gardens, this 15.2-acre garden advocates the importance of native plants and species through education in a natural conservation habitat.
The garden is a major migratory stopping point for neo-tropical birds from places as far as South America and is home to many rare birds in the Florida Keys. Enjoy this tropical forest and garden for a chance to view rare butterflies, migratory and resident birds, tropical and subtropical plants, and beautiful flowers. Many of us queens love to bird-watch and nature hike … the gardens are the perfect environs for any nature-loving gay! It is also quite expansive and with ample space to get lost with a plus one.
These gardens are expansive, great for a halfway visit, ideal for some fresh flowery air, and unexpected addition to your wild or relaxing weekend in the Florida Keys. If you are seeking a truly romantic backdrop for a wedding, nuptials, special birthday, or event, the gardens are the right spot. You sincerely feel detached from society in a Caribbean jungle.
5210 College Road
Key West, FL 33040
The BluQ [hot]:
Courtesy of The Blu Q
The Blu Q Catamaran is Key West's Original Sailing Adventures for Gay Men. This daytime or evening time adventure is one of our favorite Key West pastimes. They offer snorkeling, sunset sails, kayaking and Backcountry Island Adventure Tours and have been proudly sailing Key West for over 25 years!
This Key West establishment is a great way to celebrate a momentous group event like a birthday, bachelor party, milestone, or life in general. They typically host about a dozen men during their clothing-optional adventures. There really is nothing like snorkeling in the buff with a bunch of friends (new or old) and you’re guaranteed to make new forever friends during your five hours at sea! Food and drink are provided and you’re permitted to BYO as well. Tickets are limited and we recommend booking in advance of your Key West arrival. If you are staying just a few blocks from the BluQ on Fleming Street at Alexander House, Island House, or Equator Resort, they may assist in your booking.
🏳️🌈 All Male Day Trips (Clothing Optional)
🏳️🌈 Sunset Sails All Male Sunset Sails and we also have an “Open to All” (21+) Sunset Sail
🏳️🌈 Private Charters Blu Q is available for Private Charter and is flexible with time and dates. Book in Advance by email or phone.
Bring your camera, you’re not going to miss capturing the sights and get to snap some photos for the gram!
120 Margaret St,
Key West FL, 33040