One of the most successful pirates in history was Zheng Yi Sao, a Chinese woman.
Historians aren't clear about her early life; she may have been a prostitute. But in her twenties she married a pirate...
In the past I have helped organize a pirate themed race at my yacht club, this is a fun race held as close to talk like a pirate day in September. Top female skipper receive "Zheng Yi Sao Award" which is flags for fun races like that.