The present work inquires into the phyto-cultural interrelationships of two Huecoid communities that inhabited Vieques and Puerto Rico (La Hueca and Punta Candelero) around 2300 years ago. The primary objectives of this investigation were, among others: to characterize for the first time the agroeconomy of these communities and to interpret the role of plants as humanized natural objects which were consciously used during the movement of these peoples across the insular Caribbean. This investigation offers the first archaeological interpretation, supported by a systematic archaeobotanical study, of some of the socio-cultural processes that made it possible for two Huecoid communities to persist and evolve in a dynamic landscape of human and natural interactions in the northern Antilles.