Conch! It’s quite a quirky word, satisfying, yet it sounds like you’re cursing…“you CONCHhead!” or “you’re such a CONCH!”…
Giggles aside, over in the gay island mecca of Key West, a conch is a legit nickname given to the locals. And this bunch of conchers sure know how to live life to the fullest!
Key West is famous for its relaxed, tolerant and queer inclusivity. Historically it’s always been different, helped by the fact that it is the southernmost point of the USA mainland, slightly cut off from the rest of Florida. This has allowed Key West to thrive as a mixed haven for an eclectic blend of people ranging from Native Americans, Spanish, freed slaves, pirates, and of course, the LGBTQ community. It has also been a bedrock for artistic talent with the likes of Tennessee Williams, Ernest Hemingway and Judy Blume all making this unassuming island their home base. Key West even has an official motto of “One Human Family“.
We absolutely loved Key West. There are so many things to do here with a really exciting gay scene along Duval Street. We’ve been to Key West several times and always had a ball on each visit. We’ve put together this detailed gay guide to Key West to include our experience trying out the best gay hotels, partying in the bars/clubs, inspiration for things to do, and more.
This is easily one of the best gay tours we’ve ever done! It’s led by a World-Class-Drag-Queen who takes your hand and leads you through the gay bars of Key West dancing and singing along the way. It’s so much fun and a great way to make new friends whilst getting a feel for the gay scene of Key West.
Find out more
The gay area of key West is based around the busy Duval Street, between Angela and Petronia Streets. There is a permanent Rainbow Crosswalk here so you can’t miss it! This small intersection forms the gay neighbourhood of Key West, largely centred around 3 large complexes forming a sort of triangle. The 3 large complexes are 801 Bourbon, Bourbon St. Pub and Aqua. Each one has around 3/4 separate bars/clubs inside which we summarise in detail below.
A few blocks from the Duval gay street is another gay bar which we love called Bobby’s Monkey Bar. See below for more about it, but it was our favourite hangout because of its relaxed and friendly “local neighbourhood dive bar” feel.
One thing we also love about the gay scene of Key West is the prominent local drag culture. Every evening stars like Miss Sushi and Randy Roberts entertain the crowds and we LIVE for it! We have never had a dull night out on the Key West gay scene that’s for sure!
Florida has THE best sunsets ever. There, we called it! Over in Key West, you’re guaranteed a stunning view every evening. One of the most romantic ways to enjoy it is aboard a sunset cruise. We did one which included champagne and hors d’oeuvres on a posh elegant sailboat. A moment we’ll never forget!
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When it comes to all-male gay resorts, Key West has some of the best we’ve tried. There are so many that we’ve put together a detailed guide to the best gay resorts in Key West, which we recommend you check out. For this guide, we’ve selected our top 3.
The one thing we’d say about accommodation options in Key West is that it’s not cheap! The island has notoriously become touristy and quite expensive that many locals are forced to have 2, sometimes 3 jobs. So, if you’re looking to splurge, you’ll be in paradise here. Otherwise, if you’re watching the pennies, we recommend checking out the listings on Misterbnb.
Why we love it
Island House is probably THE most famous gay resort in all of Florida! It’s a gay man’s haven, hosting pool parties that are pretty out there.
We went to the Sunday pool party for brunch and my goodness – I don’t think we’ve seen that many schlongs in one space at one time ever before!
We also love the fact that Island House is a real mixed crowd of gay guys of all ages.
At Island House, you can either stay the night as a hotel guest or visit as we did for the day on a Guest Pass.
In terms of room options, there are a variety of options, from the basic private rooms with street views to the more lavish luxury superior rooms. If you really wanna splurge or you’re travelling in a group of friends, we recommend splashing out on the two-bedroom apartment spread over two floors, which has its own private entrance, dedicated parking (a rarity in Key West!) and private porch.
The communal facilities are everything a gay man could possibly want! The 24-hour gym and fitness center with a full array of free weights and cardiovascular equipment including elliptical machines. What made us giggle is the name of their “five-man gang shower”…we’ll leave the rest to your imagination!
Island House also has a very busy steam room, sauna and sundeck…all of which are clothing-optional, of course! The outdoor poolside area of Island House is the most sociable, where most guys hang out at all times during the day, with a 24-hour cafe and bar alongside it.
Misterb&b is the Airbnb equivalent for the LGBTQ community. Unlike on Airbnb, you know your host is gay, avoiding any nasty surprises when you check in. It is also a great way to meet gay locals and discover the underground gay scene. Click below to get 10 € (or $10) off your first booking.
Why we love it
Alexander’s Guesthouse is one of the few gay guesthouses in Key West that is open to everyone in the LGBTQ family above the age of 18.
Women and straight allies are welcome alike here! As such it’s not as sleazy or cruisy as Island House. We found it to be a more low-key, toned-down alternative to Island House.
Alexander’s guesthouse oozes charm from every nook and cranny.
It’s set in a restored 3-story, “conch”-style home, made out of wood and set on posts – a technique in the 1800s to allow air to circulate under the floor. Alexander’s is located just around the corner from Island House and around 15 minutes walking distance to the main gay bars/clubs on Duval Street.
Alexander’s has a range of spacious modern rooms, each with super-comfy king-sized beds, private balconies and air-con (a must for my Seby). If you’re a group of 4, we recommend booking the stylish and luxurious suite called “The Apartment”. It has a “spa” inspired bathroom, private sun deck and private covered balcony with views of Fleming Street.
Communal areas include several clothing-optional sunning decks, an outdoor pool and a Jacuzzi. They also have a complimentary cocktail Happy Hour at their aptly named inhouse bar – the Pink Monkey Bar, which is also a cool place to connect with other LGBTQ travellers and also to watch Seby show off his card “magic” tricks to other guests… What was interesting about the guests is that almost all of them were returning visitors who had stayed at Alexander’s at least 2/3 times before – which also explains why it’s one of the few hotels in Key West on Tripadvisor with a rare 5/5 Excellent rating from its many reviews!
The 801 Bourbon club gets busy from around 11pm and goes on until around 4am every evening.
Once the Bourbon Boys have enticed you inside to the Garden Bar, we recommend checking out the dancing area of the Bourbon St. Pub building, particularly on their male-only “Bare It All” foam nights. It’s raucous and you’ll very quickly make plenty of new friends! We like coming to the Bourbon later in the evening at around 2am when its different bar/club sections all merge into one and the crowds spill out into the outdoor pool area outside. For the ladies, look out for their female-only “Girls Night Out” party on Tuesdays from 5pm to midnight.
The Bourbon St. Pub dance parties usually catch fire from around 11pm and go on until 4am. The entrance is located at 724 Duval Street.
Aqua dubs itself as “Key West’s Best Nightclub”. When we went on a Saturday night it wasn’t as busy as the other clubs but this varies depending on which night you go. The themed nights are usually the best to look out for because they have some impressive Burlesque shows – the annual Thanksgiving “Turkey Testicle Festival” is one of the most famous. The crowd is a mixed bag of all ages from all spectrums of our wonderful LGBTQ family.
The Aqua Sidebar parties happen evening from around 11pm and continue till 4am. The entrance is located at 504 Angela Street.
Key West is home to some of the best drag artists, like the hilarious America’s Got Talent star, Randy Roberts and one of the Gaycities “Best of 2018 Hometown Queens”, Miss Sushi. We’ve set out below some of the best drag shows in Key West to check out.
For first timers or solo LGBTQ travellers who want to quickly make friends and see the best of the gay scene of Key West, we highly recommend doing a drag tour which is led by a charismatic charming local.
The Crystal Room is La Te Da’s Cabaret Theatre, which has shows every evening. Our favourite is Randy Roberts, who was one of the funniest and most talented female impersonators we saw during our trip to Florida. Between his Cher and Bette Midler impersonations, he’ll have you in a fit of giggles throughout the entire evening. Definitely one to get tickets for!
We mentioned above how much we love the upstairs club of the 801 Bourbon complex – this is mainly because of the hilarious “801 Girls” who perform here every evening from 9pm, and again later in the night. 801 Bourbon is also where you’re likely to see the famous Miss Sushi performing and mingling amongst the crowd – another not-to-miss gem in Key West!
Every evening from 7pm the “Aquanettes” perform to a seated audience at the Aqua complex. Saturday is the big night, which has 3 shows between 7pm and midnight. The shows are pretty unique because they are targetted to all ages and feature such humble(!), shy(!!) and super demure(!!!) queens such as Inga, Faith Michaels, Elle Taylor, Jessica Deveraux and Beatrix Dixie. We recommend booking your tickets in advance online as they sell out quite fast.
Although Key West doesn’t have an “official” gay beach, these are the beaches you are most likely to find a large LGBTQ crowd:
Higgs is where the gay boys are most likely to head to. The water is usually shallow, which makes it ideal for swimming and snorkelling. Higgs Beach is located at Atlantic Blvd between Reynolds Street and the White Street fishing pier.
Smathers is one of our favourite beaches in Key West because of the long sandy beach with shallow waters. It is located at the southern end of Key West near the airport, just off Roosevelt Blvd.
This gem of a beach is named after Elizabeth Taylor who used to visit it a lot with her buddy Tennessee Williams in the 1950s. Unlike the other beaches, Fort Zachary Taylor is rocky, so remember to pack a pair of sandals. Fort Zachary Beach is located at 601 Howard England Way.
For a small island, Key West sure packs a punch when it comes to queer events! There is quite a large number to look out for. Most are organised by The Key West Business Guild – we recommend checking out their Calendar of Events for the latest info.
We’ve summarised some of the main gay events in Key West below which we recommend you check out if your trip coincides with one:
Key West Pride takes place on the 2nd week of June (except the 2020 Pride which was rescheduled to November). It is so much fun, with hilarious events like “Five Lesbians Eating a Quiche” and stand up comedy shows with celebrities like Leslie Jordan. The event culminates with the Key West Pride Parade, which starts at the Truman Waterfront, goes along Duval Street and ends at South Street.
Tropical Heat is a 4-day summer male-only event, which takes place in the 2nd week in August. It has different themed events, like the Splash! Pool Party, the Bare-only and Underwear Party and a Drag Brunch. Oh – and that infamous Sunday pool party over at Island House? Well, during Tropical Heat, those Island House pool parties morph into the Hot Naкҽd Sunday Pool Party!
Womenfest is Key West’s equivalent of Tropical Heat for the girlies and also one of the largest lesbian events in the world attracting thousands each year! This 4-day festival takes place during the 2nd week of September over the Labor Day weekend. Events include a pool party, boat party and club nights with live DJs. Find out more on the Womenfest Facebook page.
The Headdress Ball is an annual ticketed Cabaret event that takes place in October. It’s part of the Key West Business Guild’s annual fundraiser event. And it’s really popular, often selling out within weeks of tickets being released online! Entrants compete for “The Best Headdress” cash prize ($3,000 for 1st place, $1,000 for 2nd place and $500 for 3rd).
Growl! Key West’s biggest bear parties take over the island during the Bear Weekend! It usually takes place on the last weekend of October and includes foam parties, a hilarious “Butch Queen Bar Crawl”, a Bear Cruise and the “Mr Key West Bear” contest. Find out more on the Key West Bear Weekend Facebook Page.
“Passion Meets Paradise!” is the slogan of Key West’s annual film festival, which takes place in mid-November. The event is huge and takes over the whole island. During the day there are film screenings, which includes a large LGBTQ segment. In the evening, the film geek crowds spill out into the Duval Street gay bars giving the gay scene a really cool vibe!
There are no official gay saunas in Key West. However, if you’re looking for some hanky panky, Island House is your best bet. It is a male-only clothing-optional resort (read more about it above) with a sauna, steam room and plenty of cruising areas.
Weekends at Island House are particularly notorious as this is when many locals and tourists (who aren’t staying at Island House) visit on a Guest Pass.
Key West is a satisfying place for foodies with many different restaurants to check out. We’ve summarised some of our favourites below. Just remember, you’re in South Florida, so you’ll want to try the famous Key Lime Pie amongst other culinary gems!
We came to the La Te Da restaurant for dinner before going to watch their Randy Roberts show cabaret show (we repeat, do not miss this in Key West!) and loved it. From the charismatic waiters to the hilarious Head Chef, they love making guests giggle and feel really welcome. They are open all day for breakfast, brunch, lunch and dinner. Our favourites were the Onion Soup and the Hamburger La Te Da – uniquely served with Shoe String Fries. We also came for brunch and can confidently say they have one of the best eggs benedicts we tried during our entire road trip in Florida.
Latitudes Restaurant was one of our favourite romantic experiences in Key West. It’s a restaurant set on a private island called Sunset Key, which is just a short boat ride away from Key West. Seating is outdoors on the sand, complete with candlelight, with views over the Gulf of Mexico. We came during sunset which made those views particularly special. I had (and highly rate!) the Pan Roasted Caribbean Lobster Tail and Seby enjoyed the Mushroom Ragu Linguini. We both tried and loved their Key Lime Pie. Although, we both tried and loved the Key Lime Pie in every restaurant we visited in South Florida…
We found the New York Pasta Gardens completely by accident when searching on Tripadvisor for a highly rated restaurant close to Duval Street. It’s set in a pretty outdoor patio with beautifully sculptured Instagrammable fountains and a few resident tropical birds that pose for pictures. They are famous for their pasta dishes, fresh fish and steaks. For Seby he went ga ga over linguine with clam sauce, and for me, it was all about the fillet mignon. Obligatory key lime pie for dessert of course! Overall a fantastic meal: delicious food and attentive staff.
Guys, this is the west-facing side of South Florida – it’s made for sunsets! The sunsets are one of the best we’ve ever seen in all our travels. We recommend making this a thing during your trip, whether you watch it at Mallory Square or on a romantic sunset cruise, make sure you watch it every evening – it’s truly magnificent! There is, of course, lots to do in Key West, so we’ve summarised a few of our favourites here:
Our favourite “sunset experience” in Key West, which we highly recommend to other gay couples is to watch it onboard a cruise. There are many sunset cruises to choose from, but we strongly advise going for one of the more expensive ones, such as the Schooner America sunset cruise, which is the one we did. The more expensive it is, the less crowded it will be and also the quality of the drinks and snacks will be much superior – champagne with fresh shrimps, yes please!
The sunset is so famous in Key West that every evening in Mallory Square there is a whole celebration for it! It starts around 2 hours before the sunset and has lots of arts/crafts exhibitors, food carts and street performers entertaining the crowds that gather to watch. This was definitely one of our favourite spots to watch the sunset in Key West because we had the unique backdrop of the cruise ships in the background.
As well as being the hub of the gay scene of Key West, Duval Street is also a great place to stroll and for shopping. It has many different boutique shops, galleries, souvenir shops and novelty shops selling some of the funniest T-Shirts we’ve ever seen! Also, the best gay shops are on Duval Street, which includes InTouch, Graffitti and Leather Master. It’s also quite interesting seeing Duval Street during the day – a far different vibe from the evening when the bars start to open up.
We always love to use food as a way to discover the local culture in every new place we visit. There is a unique story behind every dish you eat. We tried the “Secret Food Tour“, which started with a tour around Key West with a local, exploring the architecture and getting an insight into the history. We then headed to the Bahama Village (around 3 hours from Key West) where the locals go to escape the city and learnt more about the island’s historic culinary influences.
My Seby loves butterflies! Especially the big bright blue ones. So imagine his joy at seeing a whole bunch of them flying about, feeding on old brown bananas. We both loved the Key West Butterfly & Nature Conservatory. It’s set in a greenhouse-like garden where all the many multicoloured butterflies fly around, going about their daily business. We recommend trying out your phone camera’s slow-mo setting to try and get a shot of a butterfly taking off!
One of Key West’s most famous gay residents was playwriter, Tennessee Williams (1911-1983). He lived in Key West for 34 years and left his mark here, which is celebrated in this fascinating museum. We recommend visiting because it also gives you an insight into the island’s LGBTQ history. The museum is dedicated to his life’s work through an extensive collection of photographs, first edition plays, books, rare newspaper articles and videos.
Key West is famous for being the official Southernmost Point of Continental USA (the actual southernmost point of the entire country is at Ka Lae on Hawaii’s Big Island). The Southernmost Point of Key West is honoured by a colourful signposted buoy, which gets pretty busy! There is always a queue of people waiting to get their photo with this vibrant landmark, particularly at sunset. For this reason, we recommend going at dawn when the colours in the sky are quite spectacular and there are far fewer crowds, or consider doing a guided tour with a local, which includes a stopover here.
Ernest Hemingway (1899-1961) was another famous novelist who lived in Key West at The Hemingway House (now a museum) between 1931 and 1939 where he wrote To Have and Have Not. He was famous for being as lavish with women (he had 4 wives) as he was with his interiors! At one point he had peacocks wandering around the gardens. Today, the museum grounds are particularly famous for their (very photogenic!) 6-toed polydactyly cats.
We’ve put together some handy hints and tips to help you plan your own trip to Key West. Read on to find out everything the gay traveller should know before they go.
How to get there: Most will either arrive here independently by flight, road trip (like we did) or via one of the many cruise ships that dock here. If you’re flying in, you can prebook your airport pickup online, which we definitely recommend doing to minimise stress.
Getting around: We recommend you walk wherever possible as Key West is small enough to navigate by foot. When we drove over, we left our car parked in the hotel the entire time as finding parking here is hard and can be quite expensive! There are touristic conch trains that go around Key West which are fun to try out.
Travel insurance: Travel insurance is a must! We always recommend getting it before you head off to ensure you’re covered for anything that could possibly go wrong. We’ve been using World Nomads for years and cannot recommend them highly enough. Their coverage is very comprehensive and it’s easy to make a claim online.
Safety and Security: No matter where you are, you can encounter danger when travelling. We like to use the CloseCircle “virtual bodyguard” as they can provide support wherever you are. Their service covers everything from advice to evacuation in the case of weather emergencies or unforeseen events. Read more about why we love CloseCircle in our article how travellers can stay safe.
Accommodation: There are many excellent accommodation options in Key West. We like using Booking.com to plan our trip as they have the best offers and also offer free cancellation for most listings, which is handy for when you want to be flexible with your travel planning.
Sightseeing and adventure: For more inspiration, we recommend checking out the tours on GetYourGuide. They always inspire new ideas and the booking process is super easy.
When to visit: It’s always tropical in Key West! Sunshine and heat throughout the year is the norm, which makes Key West a place you can visit throughout the year. The only thing we’d point out is that the hurricane season is between June to November, so bear this in mind before going. We visited in October / November and never had any issues.
Here’s our gay map of Key West which includes all the gay bars, clubs, hotels and sightseeing highlights we’ve mentioned in this post. Use it to plan your own amazing gay trip to Key West!
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