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Customarily, studies of urbanization in early British America have concentrated on its northern mainland seaports. This article moves beyond a thirteen colonies perspective to define and explore a Greater Caribbean urban world, with Charleston, South Carolina, at its most northerly point. In particular, the authors’ comparison of the internal dynamic of Charleston and Kingston, Jamaica, reveals an urban world that was no more dominated by the demands of the plantation sector than the northern seaports were beholden to their agricultural interiors. Significantly, however, these rich internal urban economies relied on, and were profoundly shaped by, the institution of slavery. In light of these findings, the authors thus characterize this Greater Caribbean urban zone as constituting one strand of urbanization in a larger British Atlantic world that experienced an overall expansion and diversification of the urban form across the early modern period. Most specifically, Charleston and Kingston achieved a growth rate and an economic complexity comparable to other English-speaking towns through their embrace of enslaved people and their labor. [ABSTRACT FROM PUBLISHER]