Top 10 things to do in gay Key West

Ride the entire stretch of Florida’s Overseas Highway and eventually, you’ll reach Gay Key West, a hedonistic island paradise among the Florida Keys archipelago, shaped by LGBT pioneers of the 1970s. Come to rest in the open arms of Key West’s inviting turquoise waters, revel amid eclectic LGBTQ pool parties and join an accepting family of locals who pride themselves on inclusion. Forever set to vacation mode, every day in Key West is a glittering sun-soaked celebration packed with a plethora of wild gay annual events such as Tropical Heat and Fantasyfest, topped off with all the drag nightlife a queen could wish for on Duval Street. Discover the top things to do in Gay Key West, as curated by the experts at Mr Hudson.

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1. Sail at sunset on Schooner America 2.0

What better way to experience an island sunset than on-board a classy sailboat with a glass of champagne in hand while ploughing across waves that lap at numerous Key West attractions. Sunset Sail on Schooner America 2.0 presents the perfect opportunity to do just that, on a huge teak deck surrounded by mahogany with a towering canvas sail that stretches over 3,600 feet. From the stern, watch as the kaleidoscopic skies go from azure blue to blushing peach and finally to starry black, over a period of two hours, with complimentary bevvies and hors d’oeuvres for the ride.

Photo: Bobby Burch

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Tropic Cinema provides cocktails while visitors are strongly encouraged to wear costumes

2. Get your fix of drama at Tropic Cinema

More than just a movie theatre, Tropic Cinema is an independently-run community outpost bringing film, performance and art culture together under one roof. No night at Tropic Cinema is ever the same; screening classic movies one day and ballet shows the next, as well as Rocky Horror sing-a-long events and even drunk script readings in the same week. The only non-profit movie house in Key West, the atmosphere is supportive and local. If you have time to kill, join in with one of their annual island-wide 72-hour film challenges; Tropic Cinema provides cocktails while visitors are strongly encouraged to wear costumes!

3. Pay homage to Hemingway at Hemingway House

Often misrepresented as a testosterone-charged misogynist, Ernest Hemingway is an unlikely ally of queer and non-binary people everywhere. While his prose depicts hyper-masculinity, Hemingway’s true sexuality was not so easy to pigeonhole. For a large part of the 1930s, he lived with his wife on Key West’s Whitehead Street, going fishing in the Gulf Stream and drinking on Duval Street. While many stories have been told of him, to separate fact from fiction take a guided tour through Key West’s Hemingway House, the author’s home turned museum, where descendants of his six-toed cat Snowball still lazily reside.

Hemingway House | Photo: Michelle Maria

4. Indulge your artistic streak at Key West’s best galleries

The creative energy in Key West is almost palpable and so, unsurprisingly, the island has become of a hub for a diverse mix of local and visiting artists. Take a trip to The Studios of Key West for a peek at this fascinating cadre of talent, where you’ll find a rotating gallery of exhibits across three floors. Also at TSKW, visitors can watch performances of original plays, musicals and concerts or sign up to lectures and art classes. The movie theatre on the second floor also offers film screenings of art-house movies. To delve even further into the local art scene, 7 Artists & Friends is your second stop. Solely dedicated to presenting locally sourced art, this community art gallery features sculptures, watercolours, photography and a variety of playful works from Key West’s best artists.

The Studios of Key West | Photo: Larry Blackburn

The Studios of Key West | Photo: Johnny White

5. Stroll the city’s historic streets 

Key West’s old city neighbourhoods come inlaid with Spanish, Bahamian and Cuban culture making it a wonderful place to explore. As well as where to find the majority of gay hotels Key West has to offer, Duval Street and Old Key West happen to be home to great gay nightlife and more, including galleries, historic Spanish mansions and all the best places to enjoy a Cuban coffee and perhaps a cigar.

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6. Throw off your clothes and inhibitions at Higgs Beach

While there is no shortage of gay-friendly beaches in Key West, you should know that there is a de facto gay beach on the island, and the title goes to Higgs Beach. Not only is Higgs Beach a great opportunity to catch sight of Key West’s top eye candy – ostensibly shirtless and covered in oil – but also it’s a top spot for the local community who come to socialize, snorkel and watch the sunset.

Photo: Meric Dagli

Photo: Chris Arock

7. Support local businesses, from cigars to boutiques

Immigrating from Cuba in the 1980s, with the profits of a successful tobacco plantation, the Rodriguez family have since established themselves as the longest-running cigar manufacturer in Key West. Visit the Rodriguez Cigar Factory to learn more about the ingenuity and generous spirit of the Rodriguez family, as they take you on a guided tour and teach you how to prepare and wrap your own cigar. Don’t leave without first chatting to the owner, Danny, as he will passionately let you in on all the best stories of his family’s success and heritage.

As well as stocking up on authentic cigars, another unexpected shopping experience awaits at Bésame Mucho, a boutique store off the main drag in Little Bahama. Discover a range of diverse finds, from jewellery to soaps and everything in between, spanning gifts, souvenirs and speciality products.

Photo: Dayron Villaverde

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Taste freshly prepared filets and regional favourites like Key West pink shrimp, hogfish and spiny lobster

8. Set your inner foodie free at the best markets and restaurants in Key West

To start our Key West foodie tour we go straight to Date & Thyme Organic Cafe and Market, where the chefs plate up dishes to suit any health food kick, from vegan-friendly and gluten-free to keto and paleo diet recipes. The whole space is geared towards organic living, with super fresh salads, sandwiches, soups, smoothies and juice shots, as well as fresh coffee. Adjacent to the café, Date & Thyme also stocks and small natural food market allowing customers to get their hands on organic sunscreen, herbs and supplements.

For a spot of fine dining while in Key West, take a scenic boat trip across to a private island to reach Latitudes, an upscale eatery with an exclusive atmosphere. On the menu, find the finest lobster tail and Wagyu beef alongside locally influenced dishes such as the seared grouper, all served on white tablecloths to grant you your fanciest meal yet. A far more casual foray into the local seafood scene (yet by no means less delicious) will take you to Eaton Street Seafood Market on the site of an old gas station where locals flock to pick up fresh fish and picnic fixings. You can also dine outside under the shaded awning, tasting freshly prepared filets and regional favourites like Key West pink shrimp, hogfish and spiny lobster.

Photo: Edith Huber

Date & Thyme

9. Enjoy a drag show or two at Key West’s gay clubs

Take on the night with a pit stop at Duval Street where most Key West gay bars and Key West gay resorts await. Presenting some of the finest drag shows around is the widely popular 801 Bourbon Bar, the perfect option for travellers looking to dip their toes into gay nightlife in Key West. As well as offering a packed weekly schedule of ‘Not Your Momma’s Bingo, karaoke and naughty parties, the highlight of the week aligns with the arrival of Sushi, the Grande Dame of drag, who performs with the lovely 801 Girls. Mixing raucous drag action with sophisticated styles is LGBT nightclub Aqua Key West, where the talented Aquanettes take centre stage to perform world-class drag routines. Mr Hudson recommends this unique and outrageously fun drag queen guided pub crawl where you visit some of Key West’s best bars and clubs, enjoy dancing and sing-a-longs, and spend the night in the company of a world-class drag queen.

Photo: Ana Francisconi

Photo: Julien Borean

10. Mingle at the friendliest gay bars in Key West 

Outside of drag, Key West gay bars and mixed offerings are equally worthy of a gander, with Bobby’s Monkey Bar being another top choice. Often foolishly overlooked by tourists, this intimate dive bar is a local favourite, great for lingering conversations and karaoke sessions in smoky environs served by a bartender who also happens to be an expert on gay life in Key West. Then there’s mixed bar The Roost, an essential stop for anyone craving an exceptionally prepared craft cocktail. The Roost’s roster of knowledgeable bar staff will recommend drinks based on your preferences, with a daily happy hour from 3 pm – 6 pm giving up $10 Stoli Elite Martinis and various deals on their caviar-laden bar snack menu. The Roost also doubles up as a liquor store, making it the perfect place to stock up on top shelf tipples.

Photo: Amber Kipp

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