Historical Caribbean Pirates

Ahoy, mateys! The stunning islands of the Caribbean were once a haven for all kinds of daring pirates. With pieces of eight and buried treasures at their core, phrases like “walk the plank” and “shiver me timbers!” were part of daily life. “Yo ho ho and a bottle of rum” echoed across the seas. We've curated a list of the most notorious Caribbean pirates.

The legendary Captain Henry Morgan, a Welsh privateer, instilled terror in the hearts of Spanish settlements throughout the Caribbean. Operating from Jamaica, he unleashed chaos on locations in Cuba, Panama, and Venezuela. Just hearing his name would send Spanish soldiers fleeing. At his peak, he commanded 2,000 pirates and 36 ships. After retiring, he returned to England, celebrated as a hero and knighted by the king, eventually becoming the Deputy Governor of Jamaica. Today, he is commemorated through Captain Morgan spiced rum.

The notorious Edward Teach, better known as Blackbeard, struck fear into the hearts of sailors across the Caribbean. His long, disheveled black beard and the burning fuses tied to his hat created a terrifying sight. Ships would often surrender at the mere sight of him. He made his base on the lawless island of New Providence in the Bahamas, now known as Nassau, and ravaged ports in Martinique, Anguilla, the Dominican Republic, Grand Cayman, and beyond. Captured and executed at Ocracoke Island off North Carolina's coast, it's said that his headless body swam around his ship twice before sinking. Rumors persist of buried treasure from his exploits, and he served as the inspiration for Captain Jack Sparrow in the Pirates of the Caribbean films.

Not all the fun was reserved for men; Anne Bonny stands out as one of the few female pirates. She began her adventures in Nassau, known then as the Republic of Pirates, a haven for lawless characters. There, she met and married the infamous pirate “Calico Jack” Rackham. Often donning male attire, Anne proved to be as fierce and formidable as any of her male peers. Together, they navigated the waters between Jamaica and Cuba, plundering ships. Eventually captured, Calico Jack faced the gallows, while Anne escaped by claiming pregnancy. She retired from piracy to Charleston, South Carolina, living peacefully yet surely reminiscing about her adventurous past.

Bartholomew Roberts, famously known as Black Bart, reigned as the most successful pirate in the Caribbean, capturing over 400 ships during his career. His bold and ruthless nature led him to attack any vessel in sight, plundering ports in St. Lucia and St. Barts. When fleets from Barbados and Martinique attempted to halt his rampage, he vowed revenge against the islands. He flew a distinctive pirate flag depicting himself atop two skulls, one marked for Barbados and the other for Martinique. In a show of power, he captured the governor of Martinique and executed him. Despite his fearsome reputation, Black Bart preferred tea over rum and established the “Pirate Code,” enforcing rules such as no gambling, lights out at 8 PM, and resolving disputes through duels. He is also briefly referenced in the novel Treasure Island.