This paper proposes a novel approach to measuring the progress of small island developing states (SIDS) towards sustainable development (SD) as set by the UN Sustainable Development Goals 2030. Currently, these goals do not provide adequate guidance on how countries might measure their progress towards sustainability. We use these goals and a subset of their targets to develop an index with concrete targets, through the use of pertinent sustainability indicators, that SIDS should aim to achieve a sustainable society. In addition to the three categorical pillars of SD (social, economic and environmental), we included the category Climate Change and Disaster Management (incorporating Disaster Risk Reduction). The basis of our decision is that the UN and the Intergovernmental Panel on Climate Change have both recognized the vulnerability of SIDS to both environmental hazards. Our index scores a total 70 individual indicators for the four categories to track the progress of a SIDS towards a sustainable society. Using the Caribbean nation, Republic of Trinidad and Tobago, as our SIDS case study, we report the average of the scores for each category to illustrate its progress towards sustainability. Overall Trinidad and Tobago is slowly progressing towards a more sustainably developed society. Our results show that the nation is only moderately successful regarding progress in three traditional pillars of SD, social, economic and environmental. However, Trinidad and Tobago scores poorly in the Climate Change and Disaster Management category and needs to improve in this area especially due to its vulnerability.