Sun-filled days, vibrant nightlife, day-caught seafood at locally-owned restaurants, and plenty of ways to fill the day, from water activities to cultural finds, make Key West the ultimate gay getaway. But those living in Key West know what makes the continental U.S.’s southernmost point unique: the people.
Local artist J.T. Thompson first coined the phrase “One Human Family” at the start of the millennium. Soon after, the Florida Keys adopted it as its official motto to celebrate the islands’ diverse residents and inclusive attitude. Queer culture continues to be a significant part of Key West’s identity, drawing thousands of visitors each year.
GayCites spoke with some of Key West’s leading LGBTQ+ business leaders, entertainers, community activists, and a gay couple who recently visited for the first time to hear firsthand what makes Key West so unique.
Sushi: A stiletto step forward for Key West’s drag scene
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“We’re the heart of the community,” says Sushi, Key West’s legendary drag queen and original New Year’s Eve Red Shoe Drop star. (Sushi recently passed the tradition onto celebrity impersonator Christopher Peterson.) Arriving from Oregon nearly 30 years ago, Sushi has been a pivotal part of Key West’s drag evolution, starting as a janitor at Bourbon Street Pub before convincing the owners to let her perform after her shift. The rest, they say, is herstory.
When the owners bought the venue across the street, they asked Sushi for shows seven days a week. After several years, Sushi signed an agreement to lease 801 Bourbon Bar’s cabaret venue and has continued to produce two shows per night with a roster of queens ever since. “I’ve poured my life into that place,” Sushi tells GayCities, who turned the business into a profit-sharing company to encourage the next generation to take agency over their work.
As proud as Sushi is of her staff of 14, she’s equally supportive of Key West’s notoriety as an epicenter of drag talent, where artists can make a living. “Down the street is Aqua, and they have five or six drag queens, and further down is LaTeDa, with two female impersonators who sing live,” says Sushi.
After several decades, Sushi knows her way around town. Here are some of Sushi’s favorite finds:
What to order at Point 5: The bar at Nine One Five, located in a gorgeously restored Victorian-era house, features a world-class wine list and handcrafted cocktails, but Sushi goes for the back-in-fashion espresso martini.
Create your own tasting menu at Bel Mare: Opened in 2021, this coastal Italian restaurant located at the A & B Marina (two blocks from historic Duval Street) offers half portions — perfect for a light bite before a night out or crafting a multi-course meal with your favorite foodie.
A day on the water: A trip to Key West isn’t complete without an ocean excursion. Sushi suggests Fury Key West for a catamaran sailing that can be as adventurous or low-key as you’d like. Packages include reef snorkeling, parasailing, or a live music sunset sail.
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John Bobon: A taste for Key West
Like many, John Bobon and his husband Chip Junod first experienced Key West as travelers, visiting every holiday season. When it was time for Junod to retire, Bobon somewhat jokingly suggested they leave Philadelphia and head south permanently. The couple relocated in 2019, and Bobon began working as the general manager at the newly opened Red Shoe Island Bistro.
Bobon and Junod purchased the restaurant in October 2023. The “hidden gem,” as Bobon describes it, has become an unexpected but delicious next chapter in their lives. Located a half-block of Duval Street, the restaurant’s inviting lighting, original artwork, and electric menu have quickly become a treasure among locals and visitors alike.
“Two of my favorite things are food and music,” Bobon tells GayCities. On the culinary front, Red Shoe Island Bistro’s menu showcases fresh seafood in dishes like deviled eggs with seared scallops and lobster sauce, yellowtail snapper, and Key West’s famous pink shrimp. A surprising find — Beef Stroganoff — is a family recipe from the original Polish chef.
But Red Shoe Island Bistro also offers a unique backdrop thanks to Bobon’s stylish eye. His love for music — David Bowie, in particular — is evident throughout, including original artwork by a local gay artist, Lancy Berry. Bobon also curates the playlist, which features ‘80s and ‘90s pop artists, from Whitney Houston to George Michael. Even a trip to the restroom reveals dozens of framed 45 rpm vinyl records from Bobon’s childhood.
Of course, what’s the point of moving to Key West if it’s all work and no play? Bobon’s tips for unwinding in Key West include:
A bar bite for a good cause: Bobon still loves to frequent local bars and restaurants despite working long days in the service industry. Mary Ellen’s Bar is among them for craveable burgers and snacks and for its charitable endeavors, including weekly Vibrator Races (yes, that kind), which raise funds for local charities.
Where the locals go: Many Key West locals work in hospitality, but when they need a bit of TLC, they head to the no-frills Bobby’s Monkey Bar. Happy hour runs until 8 p.m., but the late-night karaoke will leave an impression.
Throwing shade in the best possible way: If you like the beach but not necessarily the sun, Bobon recommends Fort Zachary Taylor Historic State Park (known as “Fort Zach” to locals), which offers plenty of tree-covered areas with picturesque coastal views.
Fritzie Estimond: Make a home for Key West’s next generation
When Fritzie Estimond relocated to Key West, it wasn’t to escape harsh winters. The Fort Lauderdale native headed further south for a job opportunity as a juvenile corrections officer. Her commitment to youth — particularly LGBTQ+ teens — has evolved in the 14 years since, as has her love for Key West, telling GayCities, “The island has a way of choosing its people.”
Estimond currently works as the event coordinator at the Key West Business Guild, a nonprofit founded in 1978 that promotes the destination to queer travelers. The Guild includes 500 member businesses, which also present Key West Pride (June), Tropical Heat (August), Womenfest (September), and the FantasyFest Headdress Ball (October). Estimond also finds time to sit on two board committees.
Friend Chris McNulty reached out to Estimond with the idea of starting a new nonprofit focusing on LGBTQ+ services and support. “I know what it felt like to be disregarded by my family because of my sexuality,” says Estimond. “So it’s important for me to create a safe space for kids that may have that same experience.” Queer Keys was formed, and Estimond joined as the director of community resources. The organization currently hosts a gender-expansive meet-up and programs for LGBTQ+ youth as well as parents and caregivers.
Despite the island’s laidback lifestyle, Estimond still finds time to fill her days (and nights) with social activities that celebrate all that Key West has to offer.
All the world’s a stage: Estimond discovered Key West’s theater scene and has been involved behind the scenes at The Waterfront Playhouse. Other venues include The Studios of Key West, Fringe Theater, and the Red Barn Theatre, where Estimond makes her stage debut this January in Potus.
Love for Lola: One of Estimond’s favorite food finds is Lola’s Bistro, a BYOB restaurant offering an eclectic menu that changes daily and features fresh seafood.
King of the world: Key West’s legendary drag scene now includes drag king performances at Aqua Bar & Nightclub. The complex’s Back Bar also hosts weekly Hotdog Church on Sunday afternoons, a gathering of women and friends.
Sue Cooper: Riding the wave
A buddy pass from her brother, a professional pilot, landed Sue Cooper in Key West for a spontaneous birthday trip. Barely catching her return flight, rosy-cheeked from a week in the sun, she thought, “I could totally live there.”
But Cooper’s life looked far different as a global shoe company executive. “After we left, I started feeling the pull,” Cooper tells GayCities. “I won a big award at work, woke up the next morning, and asked myself, ‘Is this all there is?’ I went in on the next Monday and quit.”
Author of four books, including Millionaire in Flip Flops, Cooper founded Lazy Dog Adventures to integrate her passion for the outdoors fully into her life. Founded in 1998, the lifestyle company offers paddleboarding, kayaking, and boat adventures throughout some of the Keys’ most picturesque settings.
And while the mangrove creeks and seagrass beds offer captivating experiences for travelers, Cooper says it’s the human connection that creates memories. “I love traveling,” says Cooper, “but I’ve never met a community and people — so kind, open, and friendly — like I’ve met in Key West.”
Cooper’s staff of 16 has become a chosen family, and they’ll often hang out together outside of work. “For me, it’s a lifestyle, and I built a business around it,” says Cooper, who considers kindness the foremost job qualification. “At the end of the day, when you look in the mirror, do you like what you see?”
When not on the water, here are some of Cooper’s favorite things to do in Key West:
A taste of heaven: Cooper and crew love to grab a bite and catch some live music at the iconic Blue Heaven, which has been serving Floridian-Caribbean cuisine since 1992.
Toss, serve, or sip: Higgs Beach has it all: Sand volleyball courts, shallow waters for snorkeling, and umbrella chairs for those looking for shade. If voyeuristic vino is more your style, settle in at Saluté! On the Beach for a glass of wine and a view of the action.
Two wheels are better than four: Cooper says her rental car sat undriven for a week the first time she visited. At approximately four square miles, Key West is easy to navigate on foot, or you can rent a bike for an even quicker way to explore.
Matthew & Michael: Love at first sight
Gay travel content creators Michael Lindsay and Matthew Schueller (@michaelandmatt) have seen the world, but Key West’s first impression in 2022 left the pair enamored with what they call an “aquamarine paradise.”
Together for nine years and married for five, Michael and Matthew had visited the Caribbean but never to the continental US’s southernmost point. “There are chickens everywhere,” Schueller tells GayCities by Zoom during one of the couple’s brief travel respites. The free-roaming birds contribute to the island’s unique character, along with muted pastel single-story cigarmakers’ cottages and late Victorian-era architecture. The pair also quickly adapted to the local energy.
“It’s a very free-spirited, happy vibe,” says Schueller. “You pick up on that as you’re walking around.” And walk they did. Key West’s “compact” footprint makes exploring Duval Street and other parts of Old Town easy, with equally convenient access to water activities.
Though it was a quick 72 hours, Michael and Matthew made the most of it. Here are some of their first-time discoveries:
Queen for a day: A coffee lover, one of Lindsay’s discoveries was Cuban Coffee Queen, a local cafe with several locations specializing in cafe con leche and pressed Cuban sandwiches layered with mojo pork and other toppings.
Sharing is caring: Santiago’s Bodega embodies the best of Key West: a social atmosphere and neighborhood restaurant where friends turn into family. The couple chatted with locals while enjoying Spanish tapas like patatas bravas and skewered shrimp and chorizo.
Secluded paradise: While Higgs Beach draws attention for its gay-gazing, those looking to spread out head to Smathers Beach, Key West’s largest public beach at a half-mile long, where jet ski rentals and beach volleyball courts offer plenty of ways to play.
Ready to start planning? Visit fla-keys.com/key-west/lgbtq
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