Gay Club Key West

Why we adore it

• A supremely friendly guesthouse welcoming all members of the LGBTQ community
• Housed within a beautifully restored historic mansion dating back to the 1800s
• Features the delightfully entertaining Pink Monkey Bar
• Offers a pool area where clothing is optional

Alexander's Guesthouse distinguishes itself as one of the rare gay guesthouses in Key West that extends a welcome to all individuals within the LGBTQ spectrum aged 18 and above.

Women and their straight allies are equally embraced here! As a result, it generally presents a less overtly "sleazy" or "cruisy" atmosphere compared to establishments like Island House. We found it to be a more subdued and understated alternative.

Every corner and space within Alexander's guesthouse exudes an undeniable charm.

Why we adore it

• An unparalleled clothing-optional paradise for gay men!
• Features lively pool parties every Wednesday and Sunday
• Offers numerous areas conducive to cruising
• Equipped with a pool, gym, sauna, and steam room

The Island House undeniably holds the reputation as perhaps THE most iconic gay resort across the entirety of Florida! It serves as a veritable haven for gay men, hosting pool parties that are renowned for their uninhibited and exhilarating nature.

We attended the Sunday pool party for brunch, and honestly, it was quite an experience - I don't believe we had ever witnessed such a significant concentration of phalluses in a single space before!

We also truly appreciate the wonderfully diverse clientele at Island House, attracting gay men from all age groups.

Why we adore it

• A distinctive establishment with a focus on wine
• Conveniently situated just around the corner from the main gay street
• A tranquil, adults-only hotel that welcomes a mixed clientele
• Features a breathtakingly lush garden area adjacent to the pool

The Gardens Hotel represented a delightful splurge for us during our visit to Key West. It stands out as one of our preferred choices for couples, effectively fulfilling all our expectations. Nestled within a charmingly antique building, it enjoys a prime location just a stone's throw from the primary gay establishments on Duval Street.

Despite its proximity to the vibrant nightlife, it emanates an atmosphere of a secluded sanctuary: absolute tranquility prevails here after dark! While Duval Street becomes quite animated in the evenings, my companion, who is a light sleeper, experienced a remarkably restful night's sleep at The Gardens.

Bobby's is, without question, one of our most cherished gay bars in Key West. It possesses the charm of a classic dive bar, akin to a gay version of the iconic Cheers, where a strong sense of community prevails and everyone seems to know one another. Its welcoming and incredibly friendly atmosphere is precisely why it holds such a special place in our hearts. The proprietor, Bobby himself, is the undeniable lifeblood and soul of the establishment, consistently engaging in conversations with patrons and ensuring that every individual feels like an integral part of a large, cohesive family. They feature karaoke every evening, commencing around 9:30 PM, with an infectious enthusiasm that encourages universal participation and sing-alongs! It genuinely fosters a warm and inviting ambiance… particularly when we serenaded the crowd with a few ABBA hits, eliciting a full bar of enthusiastic sing-alongs from everyone!

The 801 stands as a substantial gay complex, prominently situated adjacent to the iconic Rainbow Crosswalk. The 801 Bourbon Bar itself is located on the ground floor, with its sister club situated directly above (more information on this can be found below). This bar serves as an excellent starting point for enjoying a few cocktails to commence the evening's festivities. Its extended operating hours are a significant advantage if you're seeking a relaxed spot to simply socialize and converse with friends well into the early morning hours, say around 2:00 AM. They frequently host themed events that are certainly worth investigating; our personal favorite is their Sunday karaoke session, held between 4:00 PM and 8:00 PM, primarily because the talented drag queens actively participate, and these incredibly skilled performers absolutely master the art of hosting a hilariously entertaining karaoke party!

As you navigate your way down the renowned gay stretch of Duval Street, you'll likely find yourself drawn into the Bourbon St. Pub, enticed by the presence of the speedo-clad Bourbon Boys stationed outside. We certainly were! Upon entering, you'll discover what can only be described as a gay man's paradise, particularly the outdoor, male-exclusive “Garden Bar” - a spacious poolside area featuring incredibly attractive, topless staff and those undeniably hot Bourbon Boys performing right on the bar! This venue is celebrated for hosting some of the most risqué parties, including the notorious “Holiday Underwear Party”, the daring “Bone Island Bare It All” event, and a multitude of uninhibited pool parties! For the most up-to-date information, we recommend consulting their Facebook page.

Aqua presents itself as “Key West's Best Nightclub.” During our visit on a Saturday evening, we observed that it wasn't quite as crowded as some of the other establishments, although this can fluctuate significantly depending on the specific night of the week you choose to attend. The themed nights are generally the most captivating, as they often feature truly impressive Burlesque performances, particularly during holiday periods like Thanksgiving, Christmas, and New Year's. The clientele here is wonderfully diverse, comprising individuals of all ages from across the broad spectrum of our magnificent LGBTQ family.

Saloon 1 proudly holds the distinction of being Key West's premier bear bar - truly, “where real men come to play”. And play they certainly do… this establishment is unashamedly an all-male venue, the kind of place you patronize with one singular purpose in mind! The very first sight that greeted us upon entering was two gentlemen, adorned only in socks, deeply engrossed in an exceedingly passionate embrace by the bar… Saloon 1 also hosts a variety of engaging themed evenings, including the highly anticipated Friday night “Cock Shock” contest and the popular “Gear Night” held on Saturdays.

The Island House is recognized as one of the most renowned gay resorts in South Florida, particularly celebrated for its clothing-optional, male-only pool parties. These exclusive events take place twice weekly, on Wednesdays and Sundays. The Sunday gathering is widely considered the most famous and heavily attended. We joined a group of friends for brunch at this venue. It's an absolutely wild experience! We had an abundance of fun, with numerous exposed genitalia, everyone thoroughly enjoying themselves while basking in the sun, and a few eccentric drag hosts ensuring the crowd remained thoroughly entertained.

La Te Da's Sunday “Tea Dance”, while a more laid-back affair compared to its counterpart at Island House, offers an equally vibrant and engaging atmosphere. All individuals are warmly welcomed at the Sunday Tea Dance. The event features a live DJ, often a local radio personality such as DJ Rude Girl or Molly Blue. Each Tea Dance adheres to a specific theme, and tradition dictates that attendees dress accordingly (or perhaps undress!) to match the motif. Many attendees typically commence their day with brunch at Island House before migrating to La Te Da to extend the festivities.

The upper level of the 801 Bourbon complex serves as the nightclub section of the venue. Throughout the night, captivating drag shows are presented, interspersed with popular chart hits and energetic Latin pop rhythms. We particularly appreciate the 801 Bourbon club for these performances, and it's evident that many others share this sentiment - when we visited on a Saturday evening, the place was absolutely packed! However, this was in the best possible way. It's also the exclusive stage for the island's most celebrated drag queen - the illustrious Miss Sushi!

Once the alluring Bourbon Boys have successfully enticed you into the Garden Bar, we highly recommend exploring the dedicated dancing area within the Bourbon St. Pub building, especially during their male-only “Bare It All” foam parties. The atmosphere is undeniably raucous, and you'll swiftly find yourself making numerous new acquaintances! We find it particularly enjoyable to visit the Bourbon later in the evening, around 2:00 AM, when its various bar and club sections seamlessly merge, and the crowds spill out into the adjacent outdoor pool area. For the female patrons, we suggest looking out for their women-only “Girls Night Out” party held on Tuesdays, running from 5:00 PM until midnight.

Aqua proudly promotes itself as “Key West's Best Nightclub.” While our visit on a Saturday night indicated it wasn't as bustling as some of the other clubs, this observation can certainly vary depending on the specific night you choose to attend. The themed evenings are generally the most noteworthy, often featuring particularly impressive Burlesque performances, especially during major holidays such as Thanksgiving, Christmas, and New Year's Eve. The clientele is a wonderfully diverse assembly, encompassing individuals of all ages from across the entire spectrum of our vibrant LGBTQ community.

Each evening, commencing at 7:00 PM, the talented “Aquanettes” present their captivating performances to a seated audience at the Aqua complex. Saturdays are particularly special, featuring three distinct shows scheduled between 7:00 PM and midnight. What makes these shows especially unique is their broad appeal, catering to all age groups and showcasing a truly remarkable cast of queens who are as humble(!), shy(!!), and unbelievably demure(!!!) as they are talented, including performers like Inga, Faith Michaels, Elle Taylor, Jessica Deveraux, and Beatrix Dixie. We strongly suggest booking your tickets in advance online, as they tend to sell out rather rapidly.

We chose to dine at the La Te Da restaurant prior to attending their renowned Randy Roberts cabaret show (we reiterate, this is an experience you absolutely cannot miss while in Key West!), and we found the entire experience to be thoroughly enjoyable. From the engaging and charismatic service staff to the wonderfully amusing Head Chef, the entire team is dedicated to eliciting smiles and ensuring guests feel genuinely welcomed and at ease. They are open throughout the day, serving breakfast, brunch, lunch, and dinner. Our top selections from the menu were the Onion Soup and the Hamburger La Te Da - uniquely presented with a side of crispy Shoe String Fries. We also visited for their brunch service and can confidently assert that they prepare one of the most exquisite versions of Eggs Benedict we encountered during our extensive road trip across Florida.

Latitude Restaurant provided us with one of our most cherished romantic experiences during our time in Key West. This establishment is situated on a private island known as Sunset Key, which is conveniently accessible via a brief boat excursion from Key West. The dining seating is arranged outdoors directly on the sand, enhanced by the soft glow of candlelight, and offering captivating views over the Gulf of Mexico. We timed our visit to coincide with sunset, which rendered those panoramic views exceptionally special. I personally indulged in, and highly recommend, the Pan Roasted Caribbean Lobster Tail, while Seby thoroughly enjoyed the Mushroom Ragu Linguini. We both sampled, and were delighted by, their Key Lime Pie. Although, it must be noted that we enthusiastically tried and loved the Key Lime Pie at virtually every restaurant we patronized throughout South Florida…

Our discovery of the New York Pasta Gardens was entirely serendipitous, occurring while we were browsing Tripadvisor for highly-rated dining establishments conveniently located near Duval Street. The restaurant is set within a picturesque outdoor patio, adorned with exquisitely sculpted, Instagram-worthy fountains and frequented by a few resident tropical birds that obligingly pose for photographs. They are particularly celebrated for their exquisite pasta dishes, impeccably fresh fish, and expertly prepared steaks. Seby was utterly captivated by their linguine with clam sauce, while my personal preference leaned towards the succulent fillet mignon. And, of course, the obligatory key lime pie was the perfect dessert! Overall, it was an exceptionally satisfying dining experience, marked by delicious cuisine and highly attentive service.

Our most cherished “sunset experience” in Key West, which we enthusiastically recommend to fellow gay couples, involves witnessing the sunset aboard a leisurely cruise. While numerous sunset cruises are available, we strongly advise opting for one of the more premium options, such as the Schooner America sunset cruise, which was our chosen excursion. The higher price point generally correlates with a less crowded experience and, importantly, a significantly superior quality of accompanying beverages and snacks - think champagne served with fresh shrimp, yes, absolutely!

The sunset in Key West is so profoundly renowned that a dedicated celebration is orchestrated nightly in Mallory Square! This festivity commences approximately two hours prior to the sunset and features a vibrant array of arts and crafts exhibitors, tempting food carts, and engaging street performers who entertain the assembled crowds gathered to witness the spectacle. This location proved to be one of our favorite vantage points for observing the sunset in Key West, largely due to the unique and picturesque backdrop provided by the cruise ships in the distance.

In addition to serving as the vibrant epicenter of Key West's gay scene, Duval Street also presents an excellent opportunity for leisurely strolling and indulging in some retail therapy. It hosts a wide assortment of unique boutique shops, art galleries, souvenir stores, and novelty shops offering some of the most humorously designed T-shirts we have ever encountered! Furthermore, the premier gay-oriented shops are conveniently located along Duval Street, including prominent establishments like InTouch, Graffitti, and Leather Master. It is also quite fascinating to observe Duval Street during the daytime - a starkly different atmosphere compared to the evening when the bars begin to open their doors.

We consistently find that food serves as an excellent conduit for understanding the local culture in any new destination we visit. Each dish we savor carries a unique narrative. We participated in the “Secret Food Tour“, which commenced with a guided exploration of Key West led by a local expert, delving into the area's architectural heritage and offering valuable insights into its historical context. Subsequently, we journeyed to Bahama Village (located approximately three hours from Key West), a favored retreat for locals seeking an escape from the city, where we gained further knowledge about the island's historical culinary influences.

My companion Seby has a profound fondness for butterflies! Particularly the larger, brightly colored blue varieties. Consequently, you can only imagine his sheer delight upon encountering a multitude of them in flight, feeding on overripe bananas. We both found the Key West Butterfly & Nature Conservatory to be an absolutely enchanting experience. It is housed within a greenhouse-like garden environment where countless vividly colored butterflies flutter freely, engrossed in their daily activities. We recommend experimenting with your phone camera's slow-motion feature to capture the perfect shot of a butterfly taking flight!

One of Key West's most celebrated LGBTQ residents was the esteemed playwright, Tennessee Williams (1911-1983). He established his residence in Key West for a remarkable span of 34 years, leaving an indelible mark on the island, which is now commemorated in this captivating museum. We highly recommend a visit, as it also provides valuable insight into the island's rich LGBTQ historical narrative. The museum is dedicated to chronicling his prolific career through an extensive collection of photographs, first-edition plays, published books, rare newspaper articles, and archival video footage.