The Caribbean is characterised by a diversity of its landscapes, populations and languages. When perceived as a dynamic place of cultural production, it was responding to both the arrivals of new groups and internal developments in a variety of ways that produced novel forms of culture and interaction. We examine the complex issues regarding the peopling of this region, the prevalent ideas about the process, the identity of indigenous groups living on the islands, the possible source areas of incoming migrants, and the chronology of their movements. We focus on the most salient points, as well as on new understandings and insights, and present how the research of our team working in Cuba – specifically at Canímar Abajo site – contributes to these debates. Research on Canímar Abajo has allowed our team to infer the presence of two different populations – with different dietary and cultural practices – synchronously occupying a restricted geographic area in western Cuba. While Canímar Abajo was certainly an important landscape marker for populations living in the region for at least 3000 years, we suspect that it is not unique in its potential to produce unexpected results that require re-examination of our current perceptions. A growing number of systematic analyses of skeletal material from already excavated sites in the Caribbean, stable isotope studies of both dietary practices and migrations, as well as advances in aDNA extraction presented today, allow us to build a more evidence-based picture of the early peopling of the islands.