If you've watched the STARZ TV show, Black Sails, you're familiar with the concept of women as pirates in the Caribbean. But do you know why some women during the "Golden Age of Piracy" chose such a life? While many previous studies on women who chose the life of a pirate focused on their actions after they became pirates, this study sought to answer the question of why some women chose such a dangerous lifestyle. By comparing previous studies of women-pirates alongside an analyzis of gender roles and expectations during this time period, and case studies of six women who became pirates, this thesis revealed the true reasons behind why some women chose this life. This study revealed that the repressive roles and expectations enforced by the law, men, and society in the 17th and early 18th century North America and the Caribbean were the primary motivators for women who pursued a life of piracy. The results of this study indicated that the laws and assigned gender roles during this time were the main reason why some women considered the dangerous life of a pirate, where they could find autonomy and equality, preferable over the restrivtive lives they were forced to live in society.