This study represents a contribution to the pre-Colonial archaeology of the Windward Islands in the Caribbean. The research aimed to determine how the Ceramic Age (c. 400 BC - AD 1492) Amerindian inhabitants of the region related to one another and others at various geographic scales, with a view to better understanding social interaction and organisation within the Windward Islands as well the integration of this region within the macro-region. This research approached the study of intra- and inter-island interaction and social development through an island-by-island study of some 640 archaeological sites and their ceramic assemblages. Besides providing insight into settlement sequences, patterns and micro-mobility through time, it also highlighted various configurations of sites spread across different islands that were united by shared ceramic (decorative) traits. These configurations were more closely examined by taking recourse to graph-theory. By extending the comparative scope of this research to the Greater Antilles and the South American mainland, possible material cultural influences from more distant regions could be suggested. While Windward Island communities certainly developed a localised material cultural identity, they remained open to a host of wide-ranging influences outside the Windward Island micro-region. As such, rather than representing a cultural backwater operating in the periphery of a burgeoning Taíno empire, it is argued that Windward Island communities actively and flexibly realigned themselves with several mainland South American societies in Late Ceramic Age times (c. AD 700-1500), forging and maintaining significant ties and exchange relationships. Alistair Bright was a member of the Caribbean Research Group at Leiden University from 2003 to 2010 and participated in numerous archaeological surveys and excavations in the Caribbean during that time. His research interests include the archaeology, ethnohistory and ethnography of the Caribbean and South America, as well as the archaeology of island societies throughout the world in general.