When one thinks of moonshining — making illegal liquor — more often than not an image of the Appalachian mountains is the first thing that comes to mind. While it’s true that the hollers and hilltops of North Carolina, Tennessee and Kentucky were hotbeds of moonshining, there was also a great deal of activity here in the Sunshine State, the effects of which can be felt even today.
Florida’s relationship with moonshine and bootlegging is as rich and complex as the state’s vast, varied landscape. From the early days of the Prohibition era to the modern revival of craft distilleries paying homage to illegal whiskey-making traditions, the Sunshine State has long been home to an underground economy of illicit liquor production. Florida’s dense swamps, rural backroads, and expansive coastline provided the perfect conditions for moonshiners and smugglers to thrive both then and now. While often romanticized in popular culture, the business of illegal alcohol in Florida was fraught with danger, ingenuity, and ongoing battles between outlaws and law enforcement, some of which continues even today.
Prohibition and the Rise of Moonshine
In 1920, the United States ratified the Eighteenth Amendment, ushering in the era of Prohibition. The law prohibited the manufacture, sale, and transport of alcohol, aiming to curb societal issues linked to drinking. However, rather than eliminating alcohol consumption, Prohibition created an underground economy that flourished across the country, including in Florida. Despite the new law, people were thirsty, and they didn’t mind buying their liquor from underground sources. Often as not, it was almost as good, and in some ways, even easier to get, and best of all, it was tax free.
Unlike other regions where bootlegging relied heavily on land-based operations, Florida’s proximity to the Caribbean made it a prime location for rum-running. Smugglers transported whiskey, rum, and other spirits from the Bahamas into the state, with Miami serving as a major hub for illicit trade. Miami’s Biscayne Bay, with its network of islands and hidden inlets, became a favored spot for smugglers to offload cargo under the cover of darkness.
The Rum Wars
While many moonshiners focused on homemade whiskey, others turned to smuggling Caribbean rum into Florida. This practice, known as rum-running, became especially lucrative during Prohibition. Fast boats—often faster than those used by federal agents—zipped across the Florida Straits, bringing in shipments from Cuba, the Bahamas, and other nearby islands.
That, in turn, ignited the “Rum Wars.” When Prohibition started, the US Coast Guard was five years old and freshly transferred out of the US Navy to the Treasury Department. Around 9,000 Coast Guard personnel had served the nation in World War I, and with that over, the USCG was back on a peacetime footing. Most of those 9,000 left the service at war’s end, leaving the Coast Guard with a relatively paltry staff and outdated ships to battle the rum runners fast boats that were often equipped with surplus airplane engines.
In short, Prohibition caught the Coast Guard flat-footed, and they were overwhelmed by the size and scope of the smuggling operations that were created nearly overnight once the Volstead Act became law. In turn, the Coast Guard tremendously expanded: The service grew from 4,000 to 10,000 personnel, was outfitted with a fleet of new cutters that were specially designed to intercept and catch rum runners. Additionally, they were aided in their efforts by 25 refurbished Navy destroyers that had been mothballed after the war. Additionally, the Coast Guard added aircraft to the mix, and as a result, they were a formidable fighting force.
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To this day, the Coast Guard and smugglers (now running illegal drugs and immigrants) fight a tit-for-tat battle. Florida’s location and long shorelines make it an irresistible target for smugglers, and one that the Coast Guard works valiantly to defend.
The Ashley Gang
Photo: Florida State Archives
Among the most infamous figures of this era was the Ashley Gang, a group of outlaws who operated in South Florida. Led by John Ashley, the gang engaged in a variety of criminal activities, including at least forty bank and an untold number of robberies, hijackings, and, of course, bootlegging. Their success in smuggling liquor into Florida made them both feared and admired. Some locals saw them as rebels resisting an unjust law, while law enforcement viewed them as dangerous criminals.
John Ashley and his companion, Laura Upthegrove, became legends, their story immortalized in Florida’s folklore. However, their run came to a dramatic end in 1924 when police ambushed and killed several members of the Ashley Gang. Their demise marked the end of a brief but intense period of high-profile bootlegging in South Florida, but it did little to stem the tide of illegal alcohol flooding the state.
The effect was not what the federal government wanted or hoped for: instead of staunching the flow of illegal liquor onto US shores, the Coast Guard’s main effect was to drive small operators out of business, only to be replaced by five major crime syndicates that operated nationally. Their battles with the federal government set off a major crime wave the size of which had never been seen in the US. In effect, the government created a permanent underground economy that exists to this day.
Moonshining In The Woods
At the same time, Florida’s interior counties saw an explosion of moonshining—illegal distillation of whiskey, often made from corn or sugarcane. Rural areas like the Panhandle, North Florida, and the swamps of Central Florida provided ideal cover for clandestine distilleries. The thick vegetation helped hide stills from government agents, known as “revenuers,” tasked with cracking down on illegal operations
One notable hotspot for moonshining was Clay County, just southwest of Jacksonville. Law enforcement records from the late 1920s detail frequent raids, resulting in the seizure of stills and thousands of gallons of illegal whiskey. Yet, no matter how many operations authorities shut down, new ones sprang up in their place, fueled by high demand and economic necessity.
Florida’s bootlegging industry thrived in part due to the complicity of corrupt officials. Some law enforcement officers turned a blind eye, either out of sympathy for struggling locals or because they received bribes. In certain counties, sheriffs and deputies actively participated in the moonshine trade, ensuring that their own operations remained untouched while cracking down on rival distillers.
The Repeal of Prohibition and the Lingering Legacy of Moonshine
The ratification of the Twenty-first Amendment in 1933 repealed Prohibition, effectively legalizing alcohol once again. However, for many Florida moonshiners, the end of Prohibition did not mean the end of their craft. Some counties remained dry, prohibiting the sale of alcohol even after its national legalization. This kept the demand for moonshine alive, especially in rural areas where legal alcohol was hard to come by.
Even in regions where alcohol was legal, homemade moonshine remained popular due to its affordability and high potency. During the Great Depression, when jobs were scarce, many Floridians continued distilling and selling illegal whiskey as a means of survival.
One of the most enduring moonshine hubs was in Manatee County, where bootlegging continued well into the 1950s and 1960s. Reports from the time suggest that entire families were involved in the trade, with skills and recipes passed down through generations. Despite law enforcement efforts, the moonshine business proved remarkably resilient and continues to this day.
Modern-Day Moonshining: From Illegal Trade to Craft Revival
While moonshining is no longer a widespread illegal practice, its legacy remains deeply embedded in Florida’s culture. Some of the techniques once used by bootleggers have been adopted by modern craft distillers who now operate legally. In recent years, small-batch distilleries have begun producing high-quality whiskey and rum, often marketing their products as a nod to Florida’s bootlegging past.
Interestingly, some former moonshiners have even transitioned into the legal liquor business. Their firsthand knowledge of distillation, once a tool for evading authorities, is now a valuable asset in a booming craft spirits market.
Distilleries such as St. Augustine Distillery (through City Gate Spirits) and Timber Creek Distillery in Crestview emphasize traditional methods of production, sometimes using locally sourced ingredients similar to those employed by old-time moonshiners. These legal operations attract tourists interested in Florida’s history of whiskey-making, turning a once-criminal enterprise into a profitable industry. You can buy for yourself some of their offerings, and by so doing, you are taking a sip into the rich history of the Sunshine State.
