A Pirate's Playground

With the discovery of the New World in the late 15th century, so too came an age of plundering and pillaging, not least by the Spanish conquistadors themselves. Their galleons, laden with gold and silver looted from Aztec, Incan, and Mayan civilisations, formed vast fleets that sailed back and forth between Spain and Central and South America.  

It didn’t take long for this train of treasure ships to be targeted by the down-trodden settlers of the region, as well as fortune hunters, fame-seekers, and adventurers alike. The Caribbean’s myriad of islands offered a natural base from where pirates could strike, board, and rob passing ships before disappearing to their hideouts in the caves of the coves. 

Cutthroat commerce as European nations vied with one another to become the dominant power in the Americas, found pirates to be valuable allies. Pirates of fearsome repute might be approached by imperial agents to attack ships from specific countries, thinning their fleet, putting a dent in their profits, and crippling their prospects in the region. As such, a professional career in piracy proved to be a lucrative venture, even if it made one in trade just as dangerous.

The Caribbean's Golden Age of Piracy

Pirating in the Caribbean started around the 1500s and lasted some 300 years with a total of more than 5,000 pirates prowling the waters. The most prolific period for piracy here was from the 1650s to the 1730s. Pirates were rampant in these parts, terrorising the Caribbean Sea and striking fear in the hearts of hapless crews.  

A standard pirate ship held around 80 tough-as-nails sailors with an average age of 27, each worth their salt. Many came from all walks of life and were called a variety of names from filibusters to freebooters. Buccaneers were a kind of libertarian privateer particular to the Caribbean, originating from settlers deprived of their land by Spanish colonial authorities on the islands of Hispaniola and Tortuga.

The Most Revered Pirates of the Caribbean

Among the many pirates, there were some who stood out for their exploits. Most found a grizzly finish but their tales still went down in pirate legend, feared and respected, even by their captors. 

Bartholomew Roberts, “Black Bart” (1682 – 1722) raided ships off the Americas and West Africa. He was known as an excellent leader with tonnes of charisma and sharp navigation skills. His fame spread and he was considered the most successful pirate of his time. He met his end fighting against the British Royal Navy, a death that shocked the pirate world.   

Anne Bonny, (ca. 1697 – possibly 1782) is one of the most famous female pirates. She took part in battles disguised as a man, fighting alongside her husband, pirate Captain John “Calico Jack” Rackham. In 1720, she was captured and sentenced to death but managed to avoid execution because she was pregnant. She swiftly disappeared and never resurfaced. 

Sir Henry Morgan (1635 – 1688) led a powerful Jamaican fleet, notching up four hundred ship attacks during his years of piracy. After his arrest, he was sent to England where, instead of being imprisoned and executed, he was instead pardoned and even knighted by the king! He returned to Jamaica, where he was suspiciously named deputy governor.  

Edward Teach (1680 – 1718) was nicknamed “Blackbeard” because of his glorious, flowing facial hair. With his warship Queen Anne's Revenge, he had a flair for the dramatic when boarding ships, placing burning ropes on his head to give himself an ominous, ghastly halo. He was killed by the skipper Lt. Robert Maynard in brutal hand-to-hand combat.

Explore the Same Historic Waters

Thankfully for you and us, pirates in the Caribbean are a thing of the past and exist only in books and movies. Buried or hidden hoards of Aztec gold and Spanish doubloons, plundered from colonial ships, are also generally fictitious, but who really knows for sure?  

Still, our expedition cruises focus on the real treasures of Central America and the Caribbean: its stunning islands, beaches, wildlife, and culture. While the pirates here are long gone, you can be sure that adventure certainly isn’t.