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This thesis is the result of applying a novel methodology which I labelled ‘participative foresight scenario mapping’. This methodology couples participatory methods for building holistic foresight scenarios for sustainable development in Flores Island (Azores, Portugal) with a multi-criteria appraisal method, Multi-criteria mapping (Stirling, 1997), to assess these scenarios alongside five sector based regional scenarios (Secretaria Regional do Ambiente e do Mar, 2006). The main research question was to reflect on how small isolated societies, which have a distant relation with strategic decision-making centres, can define their transitions to sustainability. Small islands represent interesting cases to reflect on sustainability, these small territories distant from main decision-making centres challenge decision-making and require a consideration of the issues of scale. Islands have also been seen as small, manageable models of the world, providing the opportunity to explore innovative solutions at a scale that allows inclusion of as many different factors as possible. Small islands’ populations are especially linked to their island and they develop, by the effects of isolation, a strong particular relation to the place, the role of identity is then crucial in fostering sustainable practices adapted to the island. A succession of individual scoping interviews with twenty four regional and local decision-makers and key informants and seven focus groups with a total of thirty local lay citizens gave me the opportunity to develop two differentiated multi-sector scenarios for Flores Island which were identified as Standard and Balanced development scenarios. The Balanced development scenario reflects a desire to develop an island that bases its economy on greater self-sufficiency for agricultural products, quality and certified products, and natural conservation and valorisation. The Standard development scenario is based on economic growth through tourism and primary sector intensification, and public investment in infrastructures; this scenario can be summarized as the continuation of the actual model of development. The appraisal of both holistic narratives allows in depth exploration of the complex issues related to sustainability, such as the preference between weak and strong sustainability, that otherwise would have been too difficult to assess by such a variety of research participants. Working with holistic scenarios raised the limits of the capacity to show proficiency in a wide variety of fields. The research demonstrated the feasibility of applying the multi-criteria mapping method to support the analysis of holistic non-technical scenarios. The combination of qualitative and quantitative data brought depth to the analysis and improved the understanding of the desired sustainable futures in islands. But the quantitative appraisal was overshadowed by strong uncertainties that made difficult the identification of a best scenario. Uncertainty was explained by the risks inherent to the scenarios, the limited expertise in all the criteria, the complexity of the holistic scenarios, the time horizon (20 years), doubts on the effective implementation of the chosen scenario, and the existence of potentially disrupting external factors. The process was also the opportunity to understand the role that social capital might play in the transition to the desired future for this island. It is shown in the thesis that a successful transition to sustainable development can only be reached if the objectives are understood and shared by the population.