The History of Rum Runner Cocktail

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Before the Cocktail, There Was Contraband 

Long before the Rum Runner became a tropical favorite, the Florida Keys were a smuggler’s paradise. During Prohibition in the 1920s and early 1930s, these islands sat at the crossroads of opportunity—just 90 miles from Cuba and surrounded by hidden mangrove channels perfect for evading the law. Under cover of darkness, daring “rum runners” sped across the water in sleek boats loaded with Caribbean spirits, weaving through reefs and shoals to deliver contraband to thirsty mainlanders. Their exploits turned the Keys into a hotbed of adventure and rebellion, leaving behind tales of moonlit chases, secret caches, and barrels lost to the sea. This colorful history set the stage for a drink that would one day honor their boldness and creativity. 

The First Rum Runner is Poured 

Fast-forward to the 1970s, and the danger of Prohibition-era smuggling had faded—but the stories remained. At the legendary Holiday Isle Tiki Bar in Islamorada, surrounded by palm trees and salt air, a bartender known as “Tiki John” faced a familiar island dilemma: an excess of ingredients before a new shipment arrived. His solution was pure creativity. By blending light and dark rums with banana liqueur, berry flavors, and citrus juices, he created a drink that was bold, sweet, and sneaky-strong. Named the Rum Runner in honor of the daring smugglers who once ruled these waters, it quickly became a must-have for anyone visiting the Florida Keys. 

The Cocktail of the Florida Keys 

Frozen or on the rocks, with an extra splash of rum if you like, the Rum Runner spreads from bar to bar like a well-told story. One sip tastes like salt air, boat engines humming in the distance, and a little island mischief. Today, it’s less about outrunning the law and more about slowing downraising a glass to history while soaking up the breeze. The Rum Runner isn’t just a cocktail; it’s a liquid postcard from the Florida Keys. It celebrates a past filled with adventure and a present defined by an easygoing charm. Whether perched at a tiki bar under twinkling lights, enjoying live music in Islamorada, or watching the sunset dockside, this drink is a reminder that in the Keys, history tastes best with a splash of rum. 

Ready to Taste History? 

Next time you’re in Islamorada, head to the original Tiki Bar at Three Waters Resort & Marina and order the Rum Runner. Sip slowly, savor the flavors, and let the stories of moonlit smugglers and island creativity wash over you. In the Florida Keys, every cocktail has a tale—and this one’s legendary.