Sustainability of Small Island Developing States (SIDS) is a growing concern particularly under climate change scenarios. Under the Ecosystem Service (ES) framework, we analyse the performance of five Caribbean countries (Cuba, Dominican Republic, Haiti, Jamaica, and Trinidad and Tobago) regarding environmental and socioeconomic indicators, specifying how far each country is from an ideal threshold (Boundary Point – BP). Furthermore, the analysis provides an estimation of the potential of each country to deliver ecosystem services. Building on an existing ecosystem service’s value database, we developed the Ecosystem Services Potential Index (ESPI) to compare possibilities in each country. Linking the ESPI of each country to its distance to the BP (Boundary Point Distance – BPD), helps us detecting shortcomings and providing recommendations on what could be improved to move towards achieving self-sufficiency with high quality of life at the lowest environmental cost. However, none of the countries analyzed fall within the ideal situation where human needs are met without overexploitation of ecosystems. Nonetheless, Dominican Republic, Cuba, and Jamaica are the countries closest to achieve that goal. We conclude our findings with some recommendations to adopt Ecosystem-based Adaptation (EbA) as a leverage point towards self-sufficiency in the Caribbean.