After a life-changing diagnosis, Dutch entrepreneur Jacob Gelt Dekker decides to take a step into the unknown. Setting sail from his home in Key West, he embarks on an odyssey around the Caribbean islands, navigating treacherous waters and nations forever shaped by the Age of Discovery and transatlantic slave trade. Soon he discovers that he is not alone on his boat. With him during the long days and nights at sea are Anansi the Spider, the West African trickster, and The Flying Dutchman, doomed to sail the oceans forever and harboring a terrible secret. Together, this unlikely trio seeks to establish the truth about the history of the Caribbean. Along the way, they encounter famous pirates and unpick tales of untold riches, but also retrace the steps of the region's slaves, finding out how events in Europe, the fledgling American colonies, and Africa sealed their fates. Informed by personal experience and the people he meets on the islands, Jacob Gelt Dekker offers an unconventional account that is key to understanding the Caribbean and its peoples today.