Drag legend Randy Roberts on the allure of Key West

Randy Roberts - Key West
 Randy Roberts on Duval Street in Key West. Photo by Nick Doll Photography for GayCities.

A stroll down Duval Street reveals the living embodiment of Key West’s motto: One Human Family. The small island at the United States’ southernmost tip has long attracted artists, writers, travelers, and free-spirited individuals seeking escape from the daily grind. Drag legend Randy Roberts first visited more than 35 years ago — and it was love at first sight.

Roberts first visited Key West during a six-week stint of the touring drag show Masquerade a la Cage. “I met all these great people and made all of these wonderful friends — many of whom I’m still friends with today,” Roberts tells GayCities. The tour left the sun-drenched island for the chilly streets of Chicago (“I went from shorts and tank tops to ski parkas,” Roberts recalls). When the show closed in January, a friend offered a spare room, so Roberts returned.

Living the nomadic life of an entertainer, Roberts, once again, hit the road, headlining shows from Las Vegas to Madrid, but Key West always lingered in the back of his mind, and the connections he made would last a lifetime. Then, in 1998, Roberts was invited to perform as the surprise entertainment for a birthday party. “And I never left.”

Randy Roberts as Cher at La Te Da in Key West
Randy Roberts as Cher at La Te Da in Key West. Photo by Nick Doll Photography for GayCities

At the same time, the then-co-owner of Divas Sal Rapisardi (now Aquaplex, a five-venue hotspot featuring live entertainment, multiple bars, an outdoor garden, and restaurants) asked if Roberts could fill in for a couple of shows. A weekend turned into an extended stay and the opportunity to take his show to La Te Da, a quaint bed & breakfast with a small bar room called The Tree Top.

“Within a few weeks, it took off,” says Roberts. “Right time, right place, right product. There was a funkiness to it. A new kind of audience was coming in, looking for happiness and fun. I mean, this was gay and straight, married and single — everybody came to The Tree Top. It just exploded.”

Rapisardi’s business partner Mark Barauck took over the business and saw the opportunity to turn an unused space into the Crystal Room, a state-of-the-art showroom that still sells out and which Roberts says, “Changed my life.” Current owners Christopher Rounds and Patrick Hagerty have carried on the tradition. “They have infused life into La Te Da,” Roberts says. “They’ve made sure that it is a jewel in a crown.”

Key West: A destination with personality

Randy Roberts in Key West
Randy Roberts at Nine One Five in Key West. Photo by Nick Doll Photography for GayCities.

Roberts says that when he first arrived, one of the great draws was Key West’s local flavor. “A lot of those families are still here,” he says of the independently owned retailers, restaurants, and small businesses.  

When not performing, working on new material, or touring, Roberts recharges by spending time with close friends, hitting the gym five days a week to stay in top shape for his show schedule, and biking around town, proving that only four miles long and two miles wide, Key West is easily accessible for locals and travelers alike.

After his show, Roberts likes to head to Nine One Five’s cozy downstairs bar, which offers more than a dozen craft cocktails, an American-focused wine list, and sharable bites.

When he’s feeling celebratory or entertaining visitors, Roberts recommends Café Marquesa, one of Key West’s most notable restaurants, known for contemporary American cuisine, a gorgeous, intimate 50-seat dining room, and locally sourced seafood.

For visitors looking for Key West keepsakes, novelty items, or that extra swimsuit for a day at a nearby beach, Roberts suggests Graffiti, a local menswear store in business since 1987, or In TOUCH, packed with queer collectibles, Pride accessories, and other fun finds.

Take it outside

Randy Roberts Higgs Beach
Randy Roberts at Higgs Beach in Key West. Photo by Nick Doll Photography for GayCities.

Always ready with a punch line, when asked about the best Key West spots to enjoy outdoors, Roberts quickly suggests Fort Zachary Taylor Historical Park, “a beautiful beach, which we call Fort Elizabeth Taylor.” The southernmost state park in the continental United States features the world’s largest cache of Civil War armament, along with a favorite beach for picnics, swimming, snorkeling, and paddleboarding. Roberts also mentions Higgs Beach for terrific photo opps and a chance to chat with locals.

Roberts gets his workout onstage, delivering high-energy live vocals (including illusionary performances of some of our favorite queer icons like Cher and Bette Midler) and lightning-fast costume changes. On his days off, a relaxing afternoon al fresco at Saluté provides the ideal location to kick back and watch others strike a pose on the nearby beach volleyball courts, where some of Key West’s hottest players can be seen tossing, setting, and spiking their balls.  

When the sun sets, you don’t have to look far to take in the view. The best spots for Key West sunsets are around every corner. And while the nightly Sunset Celebration at Mallory Square draws a crowd, Roberts enjoys the more low-key White Street Pier. Located in a more residential part of the island, locals refer to White Street as the unfinished road to Cuba as it beckons visitors toward the serene Atlantic coastline.

There’s no place like home

Key West
Key West, Florida

Roberts has traveled the world, but at the end of the day, Key West is home.

“I go to all of these places, and I love the opportunities, but it’s go go go. I’m more insulated here,” says Roberts of the desire to enjoy his downtime when he’s not entertaining the masses. “I have a house, and I know my neighbors. They’ve been married 51 years, and they’ve lived in Key West all their lives. And there’s no judgment because I’m a gay man or a drag queen. I know their kids and their grandkids. It’s just me. And I love that.”

More recently, Roberts has been carrying that energy onstage, recognizing that the art form has been politicized.

“One of the unexpected positives that my show — and what we do — is to have someone open their eyes. I’d like to think that over the 25 years I’ve been doing this, maybe I’ve changed a couple of minds or broadened some horizons. It’s amazing that drag can do that.”

RELATED: Key West proves you don’t need to leave the US to have a world-class tropical vacation

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