Caribbean archaeologists have tended to focus exclusively on the prehistory of the largest islands, perhaps because large islands are believed to provide the landmass necessary to support long-term population growth and cultural development. Yet, as research here and elsewhere, e.g., the Pacific, is showing, small islands provided access to resources and landscapes that were not always readily available on the larger islands. Small islands often have superior terrestrial and, especially, marine resources; isolated ritual spaces; and more easily defended locations; although they are susceptible to more rapid overexploitation. This paper examines in detail human needs with regard to island size, demonstrating that small islands were crucial in the development of pre-Columbian Caribbean societies. Four case studies are presented to illustrate that small islands often were preferred over large islands throughout the Caribbean archipelagoes. Finally, these studies show that the prehistoric exploitation and overexploitation of small islands can provide significant insights for establishing baselines that can be used for modern management and conservation efforts.