Historically, archaeologists have pursued two basic approaches to prehistoric Caribbean colonization: those relying on historical narratives and those informed by theoretical modelling. With few exceptions, the latter have not been widely employed. Here, we introduce a behavioural ecology model used in Pacific archaeology, the ideal free distribution (IFD), to understand Caribbean migration and island settlement as a form of adaptive behaviour. We assess the sequences of Ceramic Age (post-2500 BP) colonization and overall prehistoric island colonization for fit against the predictions of the IFD using terrestrial net primary production and island area as measures of habitat suitability. We conclude that certain aspects of Caribbean colonization -the initial settlement of larger, high-quality-habitat islands and temporal pauses between migration pulses -are consistent with the IFD. Model inconsistencies observed for Ceramic Age colonization, however, are best explained in terms of the limitations of Pre-Columbian seafaring and territorial behaviour on the part of pre-existing Archaic occupants.