5 Awesome Lady Pirates to Model Your Life After

I think I can safely say the best Keira Knightley was Pirates of the Caribbean: At World’s End, Pirate King Kiera. The character arc of Elizabeth Swan is the point of the Pirates trilogy. But it’s not the far-fetched Hollywood-fable as you might think. A life of piracy gave women a chance to live freer lives than in society. Women took to the seas for the same reasons Elizabeth Swan did–they hated corsets, the freedom to love who they wanted, and the way the salt air makes your skin look amazing. 

Here are 5 Awesome Lady Pirates to Inspire Your Self-Actualization

Rachel Wall

Photo by Austin Neill on Unsplash

She was the last woman executed by Massachusetts for robbery at 29. So maybe not a superb role model, but before that, she really lived. Despite being born to a proper family, she ran away from home to marry the pirate George Wall. They left Pennsylvania to take to the high seas together. Rachel would lure ships close by screaming for help from the ship’s deck, then George and his men would ambush the would-be rescuers. She tried to “retire” and work as a maid in Boston, but couldn’t give up the life of crime. She earned her third robbery conviction after stealing a bonnet from a girl. Her sentence was death by hanging. 

Cheng I Sao

Photo by Emile Guillemot on Unsplash

Identified as the most successful pirate of all time, Cheng I Sao had a fleet of 1,500 ships and employed 80,000 sailors. Cheng I Sao means “Cheng I’s wife,” she married Cheng under the strict condition she would work alongside him to expand his power and wealth. Cheng I Sao was a prostitute before becoming the greatest pirate of all time. She excelled at bringing together small bands of pirates into her fleet. After her husband’s death, Cheng I Sao continued to rule with an iron fist, forbidding her pirates from stealing from villagers or assaulting women. She worked out a deal with the Chinese Empire for her pirates, allowing them to renounce their life of crime and receive a position within the empire. 

Anne Bonny and Mary Read

Photo by Luke Southern on Unsplash

These two best friends, and possibly lovers, both started their lives with their parents dressing them as boys because it was, in a word, easier. Anne Bonny abandoned a comfortable life to take to the seas, still dressing as a man when she laid siege to other ships. Mary Read, disguised as a man, worked as a sailor. Bonny laid siege to Read’s boat, taking her captive. The two fought side by side until the law captured their ship. Both were sentenced to hang, but were pregnant and had their executions stayed. 

Grace O’Malley

Photo by Alonso Reyes on Unsplash

Legend has it that an eagle attack left her face badly scarred. What kind of incredible life are you leading if you carry the scars of an eagle attack? She was an Irish pirate, obvs, from a good family who married Donal O’Flaherty, a chieftain with a fleet of ships. She proved to be a better leader and businessperson and took over their clan’s daily operations. An enemy clan, the Joyces, murdered O’Flaherty, leaving Grace to take over the world. While the English apprehended her, she met with and charmed Queen Elizabeth I, who granted her permission to continue raiding Irish clans until her death.