Top 10 things to do in gay Key West

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.

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.

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.

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.

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.

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.