Sustainable development has become a scientific and policy paradigm in recent years. Despite the great body of literature on this issue, there remains a lack of operational studies or applied work in this field. This text aims to provide a broad reflection on the notion of sustainability, as well as a broadly applicable framework for sustainable policies by focusing in particular on a meso - regional-level of analysis and planning. In this way concrete policy choices may be depicted and made more transparent. The use of scenario experiments and simulation models leads to a policy analysis at a proper geographical and administrative scale. The case study addressed in this book concerns the Greek Sporades Islands, where sharp conflict have arisen between the interests of fishery, nature, tourism, land development and local retailing. By using geographic information system models and regional impact methods, such conflicts can be analyzed, and compromising policy strategies can be identified systematically.