The Caribbean remains an important point of reference in contemporary debates about diaspora, postcolonialism, and much else. In this introductory essay to this Special Issue we argue that the Caribbean is more than any other part of the contemporary world – both at its core and in its outward dimensions – a precursor of several themes in the energetic pursuit of modernity: capitalism/industrialism, de-tribalization/individualization, plural identities, transnationality, the disruption and transformation of cultural and political domains and boundaries. We situate key aspects of the changing meanings of diaspora in the Caribbean context and we explore the main themes that formed the core concerns of contemporary debates about this phenomenon as well as some issues that need further exploration in future research.