The History of the Florida Rum Runners – The Real Pirates Behind Your Favorite Cocktail
The Party That Wasn’t Allowed
Back in the 1920s, the U.S. banned alcohol. No beer, no wine, and definitely no rum. It was called Prohibition (1920–1933), and Florida didn’t take it well.
Enter the Rum Runners.
They were brave (or foolish) folks who smuggled alcohol from the Bahamas and Cuba into the Florida Keys. Their boats were fast, their routes secret, and their style? Pirate-level bold.
The Real-Life Pirates of the Keys
Rum Runners weren’t new pirates—but they acted like them.
They used hidden coves, bribed officials, and sometimes even got into sea chases with the U.S. Coast Guard. Some dressed sharp, others wore rags. But they all had one goal: get the booze in, get paid, and get out.
The Florida Keys were perfect for this. Close to the islands. Full of places to hide. And home to people who liked their drinks cold and their laws a little bendy.
The Smugglers’ Toolkit
How did they do it?
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Fast boats that could outrun the law (source)
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Hidden compartments under deckboards
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Midnight drop-offs on quiet beaches
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Barrels of rum disguised as “medicine”
Some even used fake documents. One legend says a boatload of rum came in labeled as “church supplies” (PBS).
From Crime to Cocktail
By the 1950s, the Rum Runner became more than a smuggler—it became a cocktail.
The story goes that a bartender at the Holiday Isle Tiki Bar in Islamorada created the drink to use up leftover booze. It mixed rum, banana liqueur, blackberry brandy, lime, and grenadine. It was strong. It was tropical. And it was a hit.
They named it in honor of the bootleggers who had once ruled those same shores.
The Legacy Lives On
Today, Rum Runners are legal—and delicious. But the name still carries a bit of rebel spirit.
Drive through the Keys and you’ll find bars named after them, drinks celebrating them, and museums preserving the tales. They may not have flown the skull and crossbones, but Florida’s Rum Runners were the real deal.
Call to Action
Love a good drink with a good story? Raise a glass to Florida’s outlaw past—and check out our “This Is Why We Can’t Have Nice Things – Florida Life” shirt at Unlawful Threads. It’s perfect for sipping history with style.