48 hours in Key West: How to plan your gay weekend getaway

Randy Roberts - Key West
Key West drag legend Randy Roberts and resident Worth Wilsey. Photo by Nick Doll Photography for GayCities.

The grey winter months are the perfect time to dash off for a sun-soaked weekend in Key West. The destination has plenty to offer, from gorgeous weather, water sports, local cuisine, and lively nightlife, but a flexible itinerary can help maximize your visit to explore the southernmost point of the continental US. 

Key West International Airport’s convenient location makes arrival and departure a breeze, with direct flights from major hubs nationwide, including New York, Chicago, Dallas, Boston, and more. 

Drop off that weekend bag (there are plenty of LGBTQ+-friendly accommodations) and head directly to one of Key West’s best queer photo ops: the newly refreshed rainbow crosswalk at the intersection of Duval and Petronia Street. Permanently installed in June 2020 through a collaboration between the city and the Key West Business Guild, the crosswalk is a welcoming beacon for travelers and locals and embodies the city’s slogan, “One Human Family.”

Head to 22&Co, one of Key West’s best bars for craft cocktails, where the drinks are as colorful as the decor. Tutu Tuesdays have become legendary, so pack one and enjoy 22% off drinks like the tequila-based Shake Your Pom Poms or the Smooth Operator, a peanut butter martini that gives the resurging espresso version sticky competition. Then grab dinner on-site at Poké in the Rear, featuring rice bowls with fresh seafood, flatbreads, and shareable bites. 

Tutu in tow, there are plenty of stops along Duval Street, Key West’s main thoroughfare, to discover bars, restaurants, live music, and entertainment — but none quite as legendary as La Te Da and its famous cabaret venue, the Crystal Room. Drag star Randy Roberts has been headlining in Key West for nearly 25 years and is one of the venue’s featured entertainers. 

“I always thought, ‘Well, I’m gonna sound like a man, I can’t do this.’ And then I just tried, and I realized that the audience accepts the voice coming out of the face it sees,” Roberts tells GayCities. “So the combination of the look and the manipulated voice creates the illusion. I resemble them. As long as they believe it, that’s all that matters.”

Randy Roberts as Bette Midler
Randy Roberts performs at La Te Da’s Crystal Room. Photo by Nick Doll Photography for GayCities.

And believe they do. Roberts collaborates with local designers for his couture gowns, and his live-singing tributes to some of our favorite divas like Cher and Bette Midler attract diverse sold-out houses. 

A good night’s rest is in order because tomorrow is packed with Key West watersports.

Key West Weekend Getaway: Day 2

Of all the things to do in Key West, spending a day on the water should remain high on your list. It’s a way to take in the gorgeous weather, enjoy time with friends, and experience the adrenaline rush of some of your favorite watersport activities. But before setting sail, breakfast is on the menu. 

Organic café and market Date & Thyme is a spot for a healthy bite before the day’s adventures, where you can have an acai bowl, breakfast sandwich, or smoothie. Snacks and prepared foods (including plenty of gluten-free options) make planning for the day a one-stop shop. Celebrating its 15th anniversary, what was once an early 20th-century gas station has become one of Key West’s favorite spots to grab a bite or pick up other locally made goods. 

two men on a boat in Key West
Spending the day on the water is a must when visiting Key West. Photo by Nick Doll Photography

There are plenty of Key West water tours to choose from, whether you’re looking for a relaxing smooth sailing experience or something with more adventure. In addition, several LGBTQ+-owned or friendly companies are a fun way to meet other queer travelers in addition to the nightlife scene

LGBT Charters — Climb on board Bottoms Up, a 55-foot v52 Princess yacht for you and nine of your besties. This DIY option is perfect for those who want to bring their own provisions. Six hours of rental time will ensure plenty of opportunities for dolphin-watching, snorkeling, or discovering a secluded sandbar to enjoy the picture-perfect Key West weather. 

Island Vibe Charters — The LGBTQ+-owned and operated Clarebouyant, a 28-foot Edgewater crossover vessel, can accommodate 12, but captain Coleen Fitzsimmons caps her charters at six guests to make sure there’s plenty of room to spread out for fun in the sun. Tours range from four to six hours and can include snorkeling (equipment provided), leisure time on a sandbar in the lower Keys, or the best of both worlds.

Blu Q Sailing Adventures — Set sail on this all-male, clothing-optional catamaran, where you’ll quickly make friends au naturel. The four-hour day trip includes a sandbar visit or kayaking (depending on the time of year), snorkeling, and organic snacks. Sunset tours offer a scenic harbor tour and perfect photo ops for capturing those Key West weekend getaway memories. 

A taste of Key West

Conch fritters
Conch fritters are a Key West specialty.

A day on the water wouldn’t be complete without a meal celebrating the bounty of local seafood. Many of Key West’s restaurants showcase the catch of the day. Favorites include Conch Republic Seafood Company, located at a historic seaport that dates back to the 1700s. In addition to savoring signature menu items like Queen conch, freshly caught snapper, and mahi mahi, diners will be glad to know that the restaurant has been a longtime supporter of preserving the region’s ecosystem through the on-site Reef Relief Environmental Center

Michael Mosi and Drew Wenzel’s Azur puts a Mediterranean spin on exquisitely sourced ingredients, presented in a charming shaded terrace and newly renovated dining room. The longtime friends and business partners draw from their international expertise. They owned and operated a restaurant in Hamburg, Germany, for nearly a decade, and Wenzel has worked with many local chefs throughout Italy. Standout dishes include house-cured salmon carpaccio, seafood risotto, and duck confit. 

LGBTQ+-friendly Key West hotels

Key West has plenty of accommodations, whether you’re looking for a bed & breakfast, an affordable hotel, or somewhere to splurge. And for those looking to avoid tan lines, several men-only, clothing-optional resorts are a fun and inclusive option. 

The pool at Island House in Key West.
Island House

The Kimpton Key West Collection includes five different properties throughout Old Town, making your stay easily accessible to plenty of attractions, restaurants, and nightlife. Winslow’s Bungalows (named after painter Winslow Homer) includes 85 guest rooms and suites; the Lighthouse hotel showcases 18th-century architecture; the elegant Ridley House is ideal for an intimate wedding, reunion, or gathering of friends; Ellas’ Cottages provide a romantic getaway; and Fitch Lodge’s bohemian touches and short distance from bustling Duval Street make it perfect for adventure-seekers looking to unwind at day’s end.

Island House has been attracting male travelers since it first opened in 1976. Decades later, the clothing-optional resort continues to attract guests who appreciate its friendly staff and body-positive attitude. All are welcome, whether you’re enjoying a dip in the pool, an al fresco meal at the poolside cafe, or free-flowing complimentary happy hour drinks (four per guest per day). Pool parties on Sundays and Wednesdays, daily specials, and top-shelf spirits continue to make Island House a favorite destination for queer men. 

The LUXlife award-winning Equator Resort offers another all-male option. The conch-style homes (34 rooms converted from five historic homes) are each unique, with many featuring direct pool access or balconies. Complimentary coffee, tea, and grab-n-go breakfast are perfect for charging up for the day’s adventures or just making your way to a poolside lounge chair.

A morning of Key West culture

A large crowd outside Bourbon's Pub in Key West.
An exhibit at the Key West Museum of Art & History pays tribute to Sushi’s famous New Year’s Eve Red Shoe Drop. Photo by Rob O’Neal/AFP via Getty Images

Book an afternoon departure to make the most of your Key West weekend getaway, and allow enough time to explore some of the region’s cultural attractions, including queer literary icon Tennesse Williams. One of the 20th century’s great playwrights spent over 40 years visiting and living in Key West. Williams won two Pulitzer Prizes for Drama; his most famous works include The Glass Menagerie, A Streetcar Named Desire, and Cat on a Hot Tin Roof. The Tennessee Williams Museum permanent exhibition at 513 Truman Avenue includes memorabilia, typewriters used by the author, rare photographs, and other documents celebrating his achievements and shining a light on the social circles in which Williams traveled.
The Key West Cultural Pass offers admission to four museums. In addition to the Williams exhibition, travelers can experience the Custom House, Fort East Martello, Key West Lighthouse & Keeper’s Quarters. 

And for anyone familiar with Key West’s famous New Year’s Eve Red Shoe Drop, a visit to the Key West Museum of Art & History’s exhibit (May 31 – June 30, 2023) pays tribute to drag queen Sushi and 25 years of LGBTQ+ diversity and entertainment, and the perfect way to say so long but not goodbye before your next Key West vacation

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