10 unexpected finds in Key West, from sexy sailings to secluded sunsets

The chickens have the right idea. And no, we don’t mean the young, lively crowd at any of Key West’s bustling nightlife spots. We’re referring to the thousands of frivolous fowl that call the island home. 

What’s not to love? Unique, independently owned hotels, a range of dining options perfect for special occasions to grab and go, and a tropical climate to take advantage of beaches and water activities. 

GayCities canvassed the island to discover some of our favorite finds and hidden treasures to make your next Key West getaway a memorable one. 

Room with a view at the Key West Lighthouse and Keeper’s Quarters Museum

Originally opened in 1848 to protect the nearby Naval Base, the Key West Lighthouse & Keeper’s Quarters has recently been restored, and visitors can ascend the 88 steps for stunning sunset views. Those looking to wow their companions (wedding proposal, anyone?) can rent the tower for a more intimate experience. 

Best night of the month for local finds

Key West’s eclectic personality comes to life at First Fridays on Fleming, a monthly event where over a dozen local businesses converge to showcase local talent. From the Fab 500 Block to Grinnell Street, visitors can discover original art, jewelry trunk shows, book signings, live music, and more. 

A haunted firehouse and the mystery behind Tennessee Williams’ gay gardener

A visit to the Alex Vega Key West Firehouse Museum will satisfy anyone who loves to get their hands on a big hose, but for those seeking a peek into Key West’s more mysterious past, a ghost tour offers next-level chills at what paranormal investigators call the most haunted firehouse in America. The mysterious demise of Tennessee Williams’ gay gardener Frank Fontis and the curse of Station No. 3 are among the nail-biting tales told. Those who want to discover the station’s LGBTQ+  history can read Alarm in the Firehouse: A Memoir of America’s First Openly Gay Professional Firefighter by Kevin Mallinson.

Key West by bike

Key Lime Bike Tours’ new Sunset Tour hits the island’s best spots during the golden hour, from Mile Zero the starting point of US Route 1, the southernmost point of the continental US marked by that Insta-worthy buoy, and drink coupons, because why not, you’re on vacation! Prefer to explore on your own? At four miles long and less than two miles wide, Key West is easy to get around by bike (most locals do), and it’s more affordable and eco-friendly than a rental car. 

You’ll be hard-pressed to find a better sandwich

The Santiago family business has been an island staple since 1954. One of their ventures, Sandy’s Café, located at the M&M Laundromat on the corner of White and Virginia Streets, draws a crowd for the cafe con leche and Cubano, a pressed sandwich packed with ham, pork, salami, Swiss cheese, lettuce, tomatoes, pickles, mayonnaise, and mustard.

Willkommen to Berlin’s

Hidden behind A&B Lobster House, Berlin’s has been enticing a clientele with a nose for a stiff cocktail since the late 1940s. Finding it is half the adventure, beginning where Front Street meets the water and up a tiled staircase to reveal an invitingly lit space and spirit-forward cocktail menu featuring Key West classics. From the Hemingway Daiquiri to the Old Fashioned, the stiff drinks are only outdone by the savvy staff who can share some of their favorite finds around town. 

Gay all day

A visit to Key West isn’t complete without time spent on the water. And if you’re enjoying Mother Nature, why not do so au naturel? Blu Q offers the only clothing-optional, all-gay charter in Key West, where participants can enjoy the ocean breeze atop a catamaran, along with snorkeling, snacks, and socializing with friends old and new. Two-hour sunset sails are equally fun and offer stellar views.

Oceanfront dining

Key West boasts plenty of great spots for a meal, but for those looking for a wow factor and views of the Gulf of Mexico, Latitudes delivers the goods. The seafood-centric menu showcases Key West’s famous pink shrimp, locally caught grouper, and an al fresco vibe that can’t be beaten. 

Discover a beach read

While your eyes may drift from the page at LGBTQ+-friendly Higgs Beach, it never hurts at least pretending to read while checking out the crowd. Plus, you’ll be well-prepared for the trip home after a leisurely shopping spree at Books and Books @ The Studios of Key West, a branch of one of the US’s top independent booksellers. The cultural hub’s street-level space is packed with titles, following in the footsteps of Key West’s literary legacy.

A drag legend spreads her wings and flies

If there’s one thing Key West isn’t short on, it’s drag queens. But the more venues, the merrier, right? Enter the newly launched Birdcage Cabaret at Aquaplex. “We’re redoing the whole interior, a new stage, glitter on the walls, everything,” says headliner Christopher Peterson. “I want it to feel like a Parisian nightclub when someone walks in.” Peterson headlines a variety show four nights per week, with drag kings on Sunday nights and additional programming on other evenings.

Go retro at Tropic Cinema

Celebrating its 20th anniversary in 2024, Tropic Cinema and its signature aqua blue Art Deco marquee have become a Key West icon. The venue operates as a nonprofit and presents a variety of first-run films, classics, and talkbacks with some of the film industry’s leading personalities. The cinema also partners with Monroe County Public Libraries for free outdoor screenings.

Check out The Best Restaurants in Key West.

Ready to start planning? Visit fla-keys.com/key-west/lgbtq

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