Smugglers, Speedboats, and Sunshine: The Wild History of Drug Running in the Florida Keys

The Florida Keys, a string of tropical islands stretching out into the Gulf of Mexico, are known today for their laid-back lifestyle, turquoise waters, and world-class fishing. Not too long ago, these sun-drenched islands were at the heart of one of the most notorious smuggling operations in U.S. history. From rumrunners during Prohibition to the heyday of cocaine cowboys in the 1970s and ‘80s, the Keys have long been a smuggler’s paradise.

The Prohibition Era: Rum and Rebels

Before the drug trade took hold, the Florida Keys were already a hotspot for smugglers—only back then, it was rum that fueled the business. During Prohibition (1920-1933), alcohol was outlawed in the U.S., but just 90 miles away in Cuba, rum flowed freely.

Enterprising “rumrunners” used the Keys’ countless hidden coves, mangrove tunnels, and isolated islands to stash their illicit cargo before sneaking it onto the mainland. High-speed boats, often faster than the Coast Guard vessels chasing them, became the smugglers’ tool of choice. Key West, already a rowdy port town, became a haven for bootleggers, many of whom had once made their living as wreckers salvaging ships that had run aground on the coral reefs. When Prohibition ended, many of these same individuals simply transitioned to the next lucrative black-market trade: drugs.

The Marijuana Boom of the 1970s

By the 1970s, the Florida Keys had become the primary gateway for marijuana smuggling into the United States. Colombian and Caribbean cartels capitalized on the region’s remote geography and expert boaters to transport tons of cannabis into the country.

Fishermen, lobster divers, and even charter boat captains found that running bales of marijuana, known as “square grouper,” paid a lot more than hauling in seafood. It was not uncommon to see bales of marijuana floating in the water or washing up on the beaches, abandoned by smugglers fleeing law enforcement. Locals who had long struggled to make ends meet found themselves flush with cash, buying new boats, homes, and even businesses.

Authorities struggled to keep up, and law enforcement in the Keys became something of a cat-and-mouse game. Stories abound of sheriff’s deputies turning a blind eye, or even taking a cut to let shipments pass through. With its laid-back, anything-goes attitude, the Keys quickly earned a reputation as a pirate’s paradise.

Cocaine Cowboys: The 1980s and the Rise of Violence

If the marijuana trade of the ‘70s was relatively peaceful, the cocaine boom of the 1980s was anything but. The shift from pot to powder brought with it not just bigger profits but also ruthless Colombian cartels willing to use extreme violence to protect their business.

Miami became the epicenter of the U.S. cocaine trade, and the Florida Keys were the perfect smuggling route. Speedboats laden with kilos of cocaine would race from South America and the Caribbean, weaving through the islands to avoid detection. Pilots with knowledge of the area’s shallow waters and hidden channels were in high demand, and high-speed chases between smugglers and law enforcement became commonplace.

Unlike the friendly, small-town feel of the marijuana trade, cocaine smuggling brought serious crime. Shootouts, assassinations, and cartel rivalries turned South Florida into a war zone. The sleepy fishing towns of the Keys weren’t immune—local law enforcement found themselves outgunned, and corruption ran rampant.

The Crackdown: Law and Order Returns

By the late 1980s, federal agencies like the DEA and U.S. Customs launched massive crackdowns on drug smuggling in South Florida, with increased Coast Guard patrols and sophisticated radar technology making it harder for traffickers to slip through the cracks. Undercover operations, sting operations, and heavy prison sentences began dismantling the networks that had once thrived in the Keys.

As the drug trade moved elsewhere—shifting to Mexico and other parts of the Caribbean—the Florida Keys gradually returned to peaceful roots. The days of smugglers racing across the water at night with millions of dollars in contraband are mostly over, but the stories and legends remain.

Legacy: A Notorious Past, A Peaceful Present

Today, visitors to the Florida Keys can still find remnants of this wild history. Locals tell tales of hidden stashes, sunken drug boats, and high-speed chases under the cover of darkness. Museums and historical societies document the region’s smuggling past, and every now and then, a “square grouper” still washing ashore and hidden paper surprises are found inside walls from new homeowners.

While the Florida Keys have traded their outlaw reputation for tourism, fishing, and a more relaxed island lifestyle, the echoes of their smuggling past still linger in the salty air. After all, there’s a reason why the Conch Republic once declared its independence—this part of the world has always played by its own rules.