How The Rum Runner Became A Signature Drink Of Key West, Florida

"Rum Runner" is undoubtedly a fanciful, exotic name for a cocktail. And like many other spirited concoctions, this one has a backstory that's just as intriguing as the drink itself. It centers on cloak-and-dagger boats gliding in darkness between the Caribbean islands and the Florida Keys, carrying swarthy, rum-smuggling pirates, bootleggers, or crafty entrepreneurs eluding both land and maritime regulators during America's Prohibition years of the 1920s. 

Many residents in the notoriously rogue Florida islands had little intention of foregoing life's alcohol-fueled pleasures, and apparently had few qualms about sharing the spirited bounty with other landlocked regions — for a handsome price, of course. Thus, the name "rum runner" was born, which referred to the clandestine boats "running" past obstacles large and small, then unloading countless bottles of rum for secretive distribution to hidden island bars, city speakeasies, and backyard bootleg operations. 

It's no surprise that the name would eventually adorn a rum cocktail invented in the Florida Keys. Unofficial cocktail historians credit the island village of Islamorada with churning out the first Rum Runner drink in the 1950s. Reportedly created by "Tiki John" Ebert at the then Holiday Isle Tiki Bar, the original Rum Runner eventually became a signature cocktail of the Florida Keys, heavily co-opted into the bar and restaurant scene of Key West. As the most populated — and popular — island in the chain, with millions of visitors every year, Key West cradles the infamy, intrigue, and history of the Rum Runner story. 

Modern Rum Runner cocktails stay close to their roots

According to lore from the 1950s, the original Rum Runner at the Holiday Isle Tiki Bar emerged from a glorious tumble of Myer's rum, brandy, grenadine, and banana liquor. It's not unlike the modern day Rum Runner anchoring the cocktail menu at the current Tiki Bar inside Amara Cay Three Resort, a sister resort to the soon-to-open Three Waters Resort, formerly the Postcard Inn, and prior to that, home to the iconic Holiday Isle Tiki Bar. As part of Marriott Bonvoy's Tribute Portfolio, is far from the quaint island bar of yesteryear. 

But the property pays homage to its roots with a classic Rum Runner cocktail featuring Bacardi Superior and Bacardi Black rums, banana liqueur, grenadine, and embellishments of orange, pineapple, and lime. Eighty miles down the Overseas Highway, straddling the Atlantic Ocean on one side and the Gulf of Mexico on the other, similar Run Runner cocktails populate the bar menus of Key West, including the Historic Speakeasy Inn, once home to a genuine rum runner operating between Key West and Cuba. 

However, you don't have to visit Key West to enjoy this classic cocktail. Create your own using Tasting Table's Fruity Rum Runner cocktail recipe, which features Chambord black raspberry liqueur from France. Experiment with different types of rum, but resist any urge to dilute the strength; after all, the term "real McCoy" originated from a notorious rum runner, Captain William McCoy, who insisted on carrying only full-strength, high-quality booze for his runs from the Bahamas to the Florida Keys.