6 Ways to Try a True Florida Rum Runner, From Islamorada to Key West

Florida’s colorful cocktail history starts with a coastline made for smuggling, a generation of seafaring outlaws, and the heady promise of Caribbean rum just beyond the reach of U.S. law. During Prohibition, boats would anchor just outside the government’s jurisdiction — what became known as Rum Row — and runners would ferry barrels of illicit spirits to waiting customers onshore.

One of the most infamous, “Captain” Bill McCoy made his runs between Bimini and South Florida and became known for selling uncut, unadulterated liquor, earning him the legacy behind the phrase “the real McCoy.”

This shadowy underworld of Prohibition pirates became the first puzzle piece I traced while researching and writing my book, Florida Cocktails. What I discovered wasn’t just a story of smuggling but one of identity. Rum wasn’t just contraband; it was culture. And eventually, it became the foundation of one of the Sunshine State’s most enduring, misunderstood drinks: the Rum Runner.

From illicit to iconic

Fast forward to 1969. Holiday Isle Tiki Bar in Islamorada was an unapologetically kitschy escape: bamboo furniture, beach views, Polynesian masks, and a bartender named John Ebert trying to offload some leftover banana and blackberry liqueurs. What he created became the Rum Runner — a sweet, fruity concoction that captured the island’s lawless energy and laid-back vibe in a plastic cup.

“It offers a sensory journey,” says Hicham El Ibrik, manager of the recently revamped Three Waters Resort & Marina, which now occupies the original tiki bar site. “With its balanced mix of rum, banana and blackberry liqueurs, and tropical juices, it’s visually stunning and incredibly refreshing.”

Today, that drink is having a quiet renaissance — not in hotel blenders or on poolside menus, but in the hands of bartenders who are rethinking its structure, sourcing, and story.

The craft awakening

In St. Augustine, Boat Drinks Bar co-owner Rob Crabtree remembers trying unsuccessfully for years to find a version of the Rum Runner he didn’t hate.

“I think the original was fundamentally flawed,” he says. “It was thrown together to use up leftovers. But there’s something charming about that, too — it’s very Florida.”

Crabtree went through more than 20 recipe iterations before landing on the version that finally made the bar’s menu: a carefully layered cocktail built (not shaken), with a base of unaged and dark rums, French blackberry liqueur, banana liqueur, and a magic juice ratio of two parts pineapple to one part orange.

“It’s such a simple drink,” he says. “But blackberry liqueur is finicky. It can turn muddy fast. Shaking it kills the brightness. So we build it gently to let the fruit shine.”

His partner, Whitney Hobbs, adds: “It’s all about quality. If you use good versions of the banana and blackberry liqueurs, the drink sings.”

A tropical classic meets new school craft

In Daytona Beach, the team at Mama Foo Foo is doing things nobody expected in a town better known for bike week than elevated imbibing.

“We’re probably one of the only places around here doing craft cocktails,” says bar manager Pants Kitchens. “But the Rum Runner hits a sweet spot — it’s familiar, approachable, and gives us a chance to show off what great ingredients can do.”

Their version includes a blend of rums: Plantation 3 Star, Cruzan Black Strap for depth, and a float of funky Smith & Cross. They use cold-pressed pineapple juice, fresh Florida orange juice, and serve it in a snifter with a giant bouquet of mint, Luxardo cherry, and orange peel. “It’s like a tropical flower arrangement,” Kitchens says, “but balance is key. You can’t fake your way through this drink.”

From dive bars to destination rums

Not every Rum Runner is clarified, stirred, or garnished with hand-plucked mint. At Jetty Lounge in Fort Pierce, the frozen version has been a hit since 1976. Served strong, cold, and occasionally through a drive-thru window, it’s less about nuance and more about nostalgia.

Further south, in Miami Beach, Swizzle Rum Bar & Drinkery stocks more than 150 rums and treats the Rum Runner with reverence. “The best rum cocktails, in general, are at Swizzle,” says Alexa Delgado, a local cocktail aficionado, Miami native, and restaurant manager at Primo in Orlando.

And in Key West, the Speakeasy Inn and Rum Bar keep the spirit alive — literally. Housed in one of the few Key West homes with a basement (ideal for stashing bootleg rum), the building once belonged to Raul Vasquez, who ran a speakeasy and smuggling operation out of the back during Prohibition. Today, it honors that legacy with more than 300 rums, legendary Painkillers, and a Rum Runner served with a wink and a story.

Florida, in a glass

The Rum Runner is not just a cocktail. It’s a love letter to the tropics. A nod to the rogues who sailed too close to the law. And maybe most of all, a reminder that great drinks don’t have to be perfect to come with a great story.

“It’s a true Florida creation,” says Crabtree. “And that’s what makes it fun.”

In the hands of today’s bartenders, the Rum Runner lives on — not by erasing its humble, haphazard origins, but by leaning into them. After all, Florida’s always had a thing for pirates.