Meet The Real Pirates of the Caribbean

Blackbeard's Pirate Flag
© Wikipedia Commons

Captain Jack Sparrow may be the first brigand that comes to mind when you think of pirates in the Caribbean, a lighthearted scalawag loosely representing the many real buccaneers who plundered for wealth, women, and pride. And, while the Pirates of the Caribbean movies may stray from truth in more ways that one (Ghost ships? Armies of undead men? Orlando Bloom being undesirable? Pah!), there is truth in its geographical orientation. Pirates did roam the Caribbean, with major lairs in Haiti, Jamaica, and Nassau, Bahamas (the latter the lair of famous pirates Calico Jack, Anne Bonny, and Mary Read).

And while they may have been more unpleasant people than Johnny Depp, their stories have lasted long past their last sail on the bounding main. 

As you may recall from the Pirates movies, Tortuga on the northern coast of Haiti was a bustling port populated by pirates in the early 17th century, as well as an active trading post for the Spanish, French, and English. As a counter to the debauchery of these rowdy sea travelers, the government at the time brought 1,000 prostitutes to the island, hoping to get the men to stop fighting each other and focus their energies elsewhere. It would not be far-fetched to assume that the scenes in Tortuga from Pirates of the Caribbean are close to truth – give or take a few pigs and key-fetching pooches.


Perhaps the most well-known real pirate, renowned both for his intense cruelty and epic heists, was Captain Edward Teach, better known to the world as “Blackbeard.” Blackbeard first served on a warship in Jamaica before deciding to take his own creative agencies by stealing a privateer and setting up his own base in North Carolina. From here, he intercepted ships sailing past the American coast, killing the crews and burning the boats, saving the goods to sell for hefty profits. 

Bartholomew Roberts, a.k.a. Black Bart, was both less brutal and more successful than Blackbeard or Francois L’Olonnais (a French Caribbean pirate known for hacking his victims to pieces), and the story of Henry Morgan may be the most incredible: starting out as a privateer (basically, a pirate operating with the blessing of one sponsor country or another), he ended up being knighted by Great Britain and named royal governor of Jamaica.

Pirates roamed the Caribbean Sea for most of the 17th and 18th centuries, challenging the English, French, Spanish and other world powers vying for control of the region. However, the life of a pirate was rarely glamorous. Pirates notoriously spent all of their money on women and booze, finding themselves bereft over and over again, thus increasing their need to continue plundering and stealing.

With the dawning of better ships, better organized navies, and better weapons, pirates were more or less run out of the business by the 19th century. Governments that had turned a blind eye to piracy, even seeing it as an effective tool to harass their enemies, began hunting down pirates, many of whom who had turned to raiding slave ships. 

Despite a rather short-lived Golden Age for pirates (usually marked as 1650s-1730s), their legacy lives on today throughout the Caribbean. In Nassau, Bahamas, pirates such as Charles Vane, Calico Jack, and Blackbeard are still remembered for their devious antics in and out of Caribbean waters. In Port Royal, Jamaica, once the pirate capital of the Caribbean, stories are still told of notorious pirates like Henry Morgan and Christopher Myngs, who dominated the scene until Port Royal was hit by a series of earthquakes in the 17th century that sent much of the port cascading into the sea.


Other islands, including the Cayman Islands, Aruba, and St. Vincent, also have claims to pirating fame, though almost no Caribbean island was left untouched by the swashbuckling, gold-plundering real-life pirates of the Caribbean. Go to almost any Caribbean island today, and you’ll be sure to see the famous symbol of pirates everywhere: the skull-and-crossbones flags that told other ships, “Surrender, or face the consequences.” Of course these days you’re likely being asked to give in to a few hours on the beach and a draught of good old Caribbean rum, to which we can only say, “Yo-ho!”