A review of the socio-political history of the Caribbean and a discussion of the development of archaeology in the region provides the context for this research. The research focus is explored through the creation of a comprehensive database of Cuban archaeology. Analysis of this database reveals that of the 1061 previously excavated archaeological sites in Cuba, only 31 are located on offshore islands. Therefore, it became apparent that it was necessary to generate further archaeological data with which to study prehistoric island interaction. Archaeological fieldwork was carried out in northern Cuba over four successive field seasons. An aim of this fieldwork was to expand the number of known archaeological sites on offshore islands in Cuba and generate a body of archaeological material with which to study prehistoric island interaction. Systematic archaeological survey was conducted in a 2000km2 case study area that included 22 islands in the Jardines del Rey archipelago. Archaeological excavations were carried out on 7 islands and a large assemblage of archaeological material was recovered. Artefact analyses were carried out at laboratories in Cuba and additional material was exported for further scientific analyses in the laboratories of UCL Institute of Archaeology. This research provides evidence of prehistoric island interaction in a case study area of northern Cuba. Excavations at the site of Los Buchillones on the Cuban mainland provide evidence of a settlement with stilted houses in a wetland environment with a maritime focused economy. Analysis of faunal assemblages from eight sites on offshore islands provides evidence of regular island interaction for the purposes of marine resource and subsistence exploitation. A radiocarbon dating project was conducted that collected 28 wood and marine shell samples from excavated archaeological contexts. These radiocarbon determinations provide evidence of long-term island interaction covering over 4000 years, as well as corroborative evidence of contemporaneous human activity at different sites in the case study area during later prehistoric times. This research uses GIS applications to map this evidence and to compare archaeology from the case study area with the newly created database of Cuban archaeology. Spatial analysis of the archaeological and environmental evidence for inter-site movement allows different interpretive models for prehistoric island interaction in the Caribbean to be evaluated.