When most people think of early America, they imagine a geographical region that encompasses the present-day United States. Like previous chapters in this volume, the present chapter encourages a broader conception of the region by, in this case, illuminating the importance of the Caribbean as a physical space and as an idea in early American literature. The Caribbean was a battle ground for empire. Consequently, those texts written in and about the region can tell us a great deal about European exploration and settler colonialism, transatlantic slavery, capitalism and modernity, colonial resistance, and the diasporic, migratory patterns of people, which are themes that pervade early American literature in general. This chapter, then, offers an overview of that literature, highlighting the literary contours of a Caribbean America. The discussion homes in on the anglophone Caribbean and its place within the literary imagination of English-language texts of early America and addresses three questions: How do English-language texts of early America imagine the Caribbean? How do we read those texts within the wider field of early American literature? And why does it matter?