Anne Bonny was a trailblazer. She was born (née Anne Cormac) in Ireland but emigrated with her family to what would later become the United States as a teenager. She married a sailor, John Bonny, against her father’s wishes, and sailed off with him into the figurative sunset. When her marriage turned sour, she took up with the infamous pirate John (“Calico Jack”) Rackham. Together they commandeered a ship and began pillaging along the coast of Jamaica. Although women were considered bad luck aboard ship, Anne did little to conceal her gender—unlike crewmate Mary Read. In 1720 Rackham and his crew were captured. The male crew members were hung for piracy, but Bonny and Read got stays of execution in the way only women can—pregnancy! Bonny was later released and lived the remainder of her life in a quieter fashion.

Ching Shih

Aside from being an extremely famous pirate, Ching Shih was arguably the most successful one. Little is known of her early life except that she was a prostitute, but in 1801 she was captured by—and subsequently became the wife of—a pirate named Cheng Yi. Together they sailed the seas and amassed a pirate army known as the Red Flag Fleet. Upon Cheng Yi’s death in 1807, Ching Shih took command of the fleet, which consisted of hundreds of ships and some 50,000 pirates. She kept them in line with a strict code of conduct, with most offenses being punished by beheading. The fleet proved so unstoppable—sometimes even venturing upstream in smaller boats to hit cities and towns that weren’t on the coast—that the admiral of the Chinese navy committed suicide rather than be captured by her. In the end, she was offered amnesty by the Chinese government and retired to the countryside 

• The Irish “Pirate Queen” Grace O’Malley is one of the most infamous buccaneers of any gender. Born in 1530, Grace was raised in a seafaring clan, which her father was the leader of. She married well (twice) and basically spent her time defending her property by any means necessary…and taking some other people’s property for good measure. Ruthless and fearless, legend has it that Grace gave birth to one of her sons aboard a ship, then engaged in combat a day later to defend the vessel. As if that weren’t enough, Grace proved spirited enough to request an audience with none other than Queen Elizabeth. She demanded that her brother and sons, who had been captured, be released. And the queen obliged.