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Pirates, Rum Runners, and History: Visiting Key West’s Distilleries



When your vacation time rolls around, one of the incredible places where you can travel to is Key West, Florida. This is a great adult vacation spot for those who would like to spend their time off relaxing on the beach in the sun and on the sand while enjoying flavorful adult beverages, like rum. Key West has an interesting history, mostly thanks to the role the area played during the Prohibition era.

A Little Background on Key West

In some surveys, Key West is listed as the fourth-best Floridian city to visit. Travelers are encouraged to visit the island-destination between March and May because it is when the winter travelers begin to wane off but before the summer travelers begin to arrive. This is a popular spot people like to hit for the holidays since the weather tends to be warm and pleasant and not everyone wants to have a White Christmas. Between March and May, you might find yourself among the Spring Break crowd, but you will not be there when it’s hurricane season.

It is said that the residents of Key West have a live-in-the-moment philosophy. For tourists, this is a great seaside adventure. The island is the southernmost area of the United States. When the Spanish explorers were hanging out in the location, they found human bones, so they named it Cayo Hueso. In 1815, the Spanish crown granted the island to its officer Juan Pablo Salas. In 1822, he sold it to John Simonton, an American businessman. The island has its fair share of importance in American history.

As a center of American military operations, it was an important city during the 1898 Spanish-American War. It is also a cultural site. There is a mix of Cuban, West Indian and Bahamian cultures in addition to American. The former homes of writer Ernest Hemingway and ornithologist John James Audubon still stand.

Why Did Rum Running Begin?

One of the fun and interesting tidbits about Key West is the role it played during Prohibition and the Rum-Running era. On January 17, 1920, Prohibition was enacted in the United States. Prohibition disallowed the manufacturing, sale and transportation of alcoholic beverages within the U.S. The goal was to reduce crime and corruption. It was trying to solve social problems and reduce the tax burden created by prisons and poorhouses as well as improve health and hygiene in America. The early 1900s saw a lot of people flocking to the United States because populations in Europe were living longer. Some of the social problems that were being created were simply due to differences in culture, but the government decided that legislation would solve them. However, on December 5, 1933, politicians realized that they could not legislate morality, so Prohibition ended.

The United States Government probably did not anticipate the rebellious nature of its citizens. The 1910s saw the growth of the Industrial Revolution and cities, so times were changing anyway. Since alcoholic drinking became prohibited, the defiant personalities of the progressive mindset were ignited. Prohibition was turned into a lifestyle that led to the flourishing of the speakeasy, the flapper and the rest of the culture that defined the Roaring 20s. The very mobsters who the police and government were trying to stop turned the legislation into another business. In contrast, others simply wanted in on what turned out to be fun and parties. Thanks to Prohibition, therefore, rum-running became the practice of getting alcohol to the United States illegally through oversea means.

What Was Rum Running?

Rum running essentially began January 17, 1920, when Prohibition was enacted. It ended when the law was repealed on December 5, 1933. For those 13 years, alcohol was still manufactured, sold and consumed in the United States. It was just done so in secret. Producers of wine took it as far as fermenting the grapes and selling them in a gelled block that simply needed to be diluted by the consumer. Others smuggled in bottles of alcoholic beverages by land and sea.

Those participating in the illegal activity of importing alcohol into the United States from overseas were known as the rum runners. They managed to get whiskey, rum and other liquor, like Scotch, among others, into the country. Individuals attempted to manufacture low-quality alcoholic drinks in-house, but the taste was so bad, it is said that consumers were waiting for the boats and buying the Scotch right off the boat. Additionally, the questionable drinks being manufactured were so poor in quality, they were dangerous. Drinks were being imported by sea from Europe, Canada and the Caribbean. The supply mostly ended up at speakeasies. The wealthy also got ahold of some of the merchandise, which they consumed at their underground, lavish parties.

The rum runners ran shipments of whiskey, rum and Scotch, among other alcoholic drinks, such as sparkling wine. The countries and cities that the runners procured the contraband from included Great Britain, Nassau in the Bahamas and throughout the Caribbean. The illicit contraband would then be taken by sea to the port cities of the United States, including up and down the East Coast to places like New Orleans. Canada was another whiskey provider. The drink would get distilled in Canada and then smuggled by ship. The runners handled the sea leg of the run, whereas the bootleggers handled getting it to the West Coast. Contraband made its way to the Midwest from Saskatchewan and Ontario. The East would receive shipments from Nova Scotia and St. Pierre, a French island that’s just off the coast of Newfoundland.

As the law enforcers began to catch on to what was happening by sea, the captains of the boats had to get smarter and more creative. False bottoms were constructed where the alcohol would be hidden. Then, fish were poured on top. The golden years for these men took place in the early 1920s before the Bureau of Prohibition Agents and other authorities, including the Coast Guard, caught on to what was happening offshore. Smugglers also set up a system with contact boats. The law could only go out 12 miles before it was considered to be international water. Beyond those 12 miles, American law no longer applied, so outside of that line, it was fair game.

That border, in some areas, became known as Rum Row because the boats with the large loads would meet smaller boats that bought the merchandise. Small, high-speed boats would toss their money onto the ships. Then, they would speed away like bandits with their contraband. The runners were good at the system that they set in place. In 1923, Commandant William E. Reynolds was frustrated with not being able to catch the runners, so he asked the federal government for more help. His crew grew in size to 11,000 officers.

Who Are Notable Figures of the Rum Running Years?

When most people who have some knowledge of the Prohibition era think about the famous figures, they probably think of Bugs Moran, Meyer Lansky and Al Capone. These men are famous because their dealings took place in New York City and Chicago. Southern Florida also had their suave men and women who used their wits to rake in a small fortune in this area of the United States. In Southern Florida, Bill McCoy, Cracker Johnson, Gertrude Lythgoe and Marie Waite worked their magic.

McCoy never technically broke the law. Nonetheless, officials in Washington, D.C., investigated him. Although Capone was famous, McCoy was the face of the Prohibition era. McCoy loved the water. He was born in New York, but he moved from there to Philadelphia and, eventually, Florida. In Florida, he went into the boat-building business with his brother, Ben. Their business took off, and they built sailboats for the Vanderbilts, John Wanamaker and Maxine Elliott as well as Andrew Carnegie. They expanded into a boat service that went from Jacksonville to Palm Beach as well as Fort Myers through the Everglades. McCoy found himself falling on hard times as the Prohibition Act was put into place. Lore says that a stranger made McCoy an offer that he could not refuse.

He was well-positioned to begin his rum running career since he knew the boat and sailing business inside and out. McCoy was asked to make the sail from Southern Florida to Nassau in the Bahamas. The Bahamas needed to sell their rum, and Americans were itching to buy it. He convinced his brother. They sold their boatbuilding business and used the profit to fund their new venture. To protect himself, McCoy bought a new boat and registered it as a British vessel. It was not difficult for the brothers to amass commissions. The brothers figured out that as long as they remained on international waters, they were not breaking any laws.

McCoy’s fleet grew to an armada of five boats. It is estimated that they moved a total of 2 million bottles in a career that was short. He became known as “The Real McCoy” because he was deemed the most reliable among the runners and bootleggers. He never watered down the product, and so he could set the price. Plus, he offered a good time that eventually attracted tourists and jazz musicians. McCoy set the standard that was adhered to by everyone else on Rum Row. Unfortunately, he became so well-liked and famous that the media and law enforcers began to investigate what was happening and how he was getting away with the illegal activity. It did not help that he was making the Coast Guard and others look foolish because he still was not technically breaking any laws. In 1923, the Henry L. Marshall was co-signed to another runner. The story has it that the boat was seized in international waters. One of the crew members was drunk, and he spilled all the beans to authorities.

Today, you can visit many sites of former speakeasies. One example is the Speakeasy Inn on Duval Street. It’s one of the few buildings in Key West that has a basement, and a secret room was built to put that underground space to good use during Prohibition. Visitors to the inn can view the secret room that was a hiding place for smuggled spirits from Cuba.

Key West First Legal Rum Distillery

The Key West First Legal Rum Distillery situated on Simonton Street in Key West is one rum spot you can visit in the area. It sits close to a historic marina as well as a resort and spa. It was established in 2012 by Paul Menta and Tony Mantia. In 1900, it was the original location of Jack’s Saloon. In 1903, it was turned into a Coca-Cola bottling facility. The owners of this distillery take pride in their craft. They consider themselves to be chefs first and distillers second. In addition to the libation, they also jar rum cakes, fresh fruits and savory vegetables.

Paul Menta is the owner and chief distiller. He is also considered to be a kiteboarding pioneer who has practiced the sport from Key West to Cuba. One of his most extreme adventures took place at 10,000 feet near three Guatemalan volcanoes. The staff is made up of distillers, mixologists and mojito-class instructors. While you are enjoying your rum and cake, you can also check out the class, which boasts that it will teach you to make the best mojito west of Havana. This class is one more feature that makes this particular distillery unique.

Cuba already boasts some of the best rum. The team at First Legal Rum decided to rum run their creation to Cuba. While in Cuba, they learned how to master the mojito.

Their Chef’s Rum Lines are available in key lime, vanilla brûlée dark, and green coconut flavors, while the Cuban Coffee Rum is made from aged, dark-roasted coffee beans. If it is mixed with coconut milk, you can make a Coconut Mud Slide.

Key West Distilling

Key West Distilling is located on Shrimp Road in Key West. It is within walking distance of the Stock Island Marina Village and Sunset Sail Key West. The distillery offers rum as well as vodka, gin and whiskey.

The owner of Key West Distilling takes advantage of the Island Time attitude of the area. He has incorporated that attitude in his distiller’s process. In conjunction with the location’s overall vibe that is perfected with the sun, palms and breezes, the rum-making process is slow. This provides the utmost care to the process so that no flavors are compromised. The best ingredients are also utilized to deliver something you will enjoy consuming.

Papa’s Pilar Rum Distillery

If you’re a literary history buff who loves Ernest Hemingway, Papa’s Pilar Rum Distillery should be at the top of your list of places to visit. This distillery claims to harness the same sense of adventure as Hemingway had on his escapades on his boat, Pilar, and place it into their rum (hence the distillery’s name). Papa’s Pilar is located at the intersection of Greene & Simonton in Key West. The rum you can enjoy here is made in the spirit of the way Hemingway lived his life. Those familiar with the author’s books know that he lived life to the fullest. He had many experiences, which provided first-hand inspiration for many of the themes for his stories. Hemingway is described as always having lived his life in constant motion. It was the boat that gave him the opportunity to go beyond the shore in order to keep living as a bon vivant. This is the spirit the distillery hopes to capture in its rum.

This award-winning rum is said to be crafted using a unique solera barrel-aging process to give it its distinct taste. To further enhance the taste, the ingredients and the rums are specially picked out from the Caribbean as well as the three Americas.

Their famous Blonde Rum is solera-blended in Bourbon barrels and Spanish sherry casks and is 84-proof. As you sip, you might experience the taste of creamy and buttery vanilla, with hints of mango, orange peel and pineapple. With their 86 proof Dark Rum, you might experience a more earthy taste that includes vegetal tones with touches of spice, bourbon and almond as well as apricot. Both are rums you won’t want to miss trying when you make your way to Key West.

Key West is ninety miles north of Cuba, and it’s a popular cruise-ship stop. The island destination is known for its coral reefs, snorkeling opportunities and diving spots as well as its sandy beaches. Additionally, it is a great location to savor carefully curated rum and learn more about the rum running of the Prohibition years. With all its history and charm, Key West is a great place to visit if you want to have a great rum-tasting experience.

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