This book explores the intersection of migration, identity development and the school achievement of Caribbean heritage children. In doing so, it uncovers the history of the Caribbean and its early inhabitants such as the Siboneyes, Guanahatabeyes, Tainos, Caribs, and Arawaks, who predated the arrival of European explorers and enslavers, and it explains the relevant connections to colonialism, neo-colonialism and Caribbean migration to North America. Through family interviews, it presents perspectives on Caribbean immigrants in North American schools (United States and Canada). The book further explains what happens when these immigrants transition from being the ethnic majority in their home country, into the minority in a foreign country. Interviews with families and personal narratives are weaved into a rich discussion on immigrant identities in school and society. The findings strongly support the treatise in the literature that Caribbean heritage families place a strong emphasis on education and school achievement.