The Real Pirates of the Caribbean

A Pirate’s Playground

The ‘discovery’ of the New World in the late 15th century brought about an unrivaled age of plundering and pillaging, particularly by the Spanish conquistadors themselves. Vast fleets of Spanish galleons sailed back and forth between Spain and Central and South America, laden with gold and silver looted from Aztec, Incan, and Mayan civilizations.

It didn’t take long for the down-trodden settlers of the region to target these treasure ships, along with fortune hunters, fame-seekers, and adventurers. The Caribbean’s numerous islands offered the perfect base for pirates to strike, board, and rob passing ships before disappearing into their cave hideouts located in the coves.

European nations actually found pirates to be valuable allies as they fought to become the dominant power in the Americas. Imperial agents occasionally approached pirates with fearsome reputations to contract attacks on ships from certain countries, thus thinning their fleet, decreasing their profits, and crippling their prospects in the region. Professional piracy proved to be quite a lucrative venture and made trade just as dangerous a job.

The Caribbean’s Golden Age of Piracy

Pirating in the Caribbean started around the 1500s and lasted for approximately 300 years. It is estimated that more than 5,000 pirates prowled the waters during this time. Piracy here peaked from the 1650s to the 1730s. Pirates were rampant, terrorizing 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. They 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 stripped of their land by Spanish Colonial authorities on the islands of Hispaniola and Tortuga.

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Photo: Andrea Klaussner and Stockdonkey / Shutterstock

The Most Revered Pirates of the Caribbean

Some pirates stood out for their exploits. They were feared and respected by even their captors, and most suffered a grizzly finish, but their tales went down in pirate lore.

Bartholomew Roberts, ‘Black Bart’ (1682–1722) raided ships off the Americas and West Africa. He was known as an excellent leader with plenty of charisma and sharp navigation skills. This won him great fame 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, (c. 1697–1782) was 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 escaped execution because she was pregnant. She disappeared and never resurfaced.

Sir Henry Morgan (1635–1688) led a powerful Jamaican fleet, counting up to 400 ship attacks during his years of piracy. Upon arrest, he was sent to England. Instead of being imprisoned and executed, he was 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’ for his glorious, flowing facial hair. With his warship, Queen Anne’s Revenge, he had a flair for the dramatic when boarding ships—he often placed 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 considered fictitious, but who really knows for sure?

Either way, our expedition cruises focus on the real treasures of Central America and the Caribbean: the stunning islands, beaches, wildlife, and culture. Pirates may be long gone, but the adventure here certainly isn’t.