In 1823, Tory Lightfoot runs away from Boston's soul-stifling Worthen Academy for Women where her rebellious nature and mixed blood are the source of constant scorn and abuse. Seeking freedom that she knows she'll never find at the school, she disguises herself as a young man and stows away aboard a merchantman bound for Barbados--only to be captured by pirates. Through a series of well-meant but disastrous choices, Tory winds up accepting the pirates' invitation to join their crew. She quickly takes to the life of an outlaw, joining the buccaneers as they plunder ships while they dodge the pirate-hunting American "West India Squadron." But the authorities turn out to be the least of her troubles, for it is her heart that tests her character and ability to survive. First there is Matty, a handsome gentleman's-son-turned-pirate out to prove himself on his own terms. There's also Jack, her mentor, who reluctantly helps her adapt to the brigand's life.