This study investigates the role that information and communication technologies (ICT) and knowledge management (KM) are playing in supporting sustainable development across islands in these countries. Focusing on the areas of health, education and governance, the study uses the multi-island countries of Saint Kitts and Nevis, Trinidad and Tobago, and Turks and Caicos Islands as case studies to explore inter-island differences in ICT and KM capacity and the scope for strengthening this capacity. It concludes with a series of recommendations for governments of Caribbean multi-island countries working to strengthen ICT and KM capacity across islands as well as areas for further analysis and investigation.