This book addresses the issue of smart and sustainable development in the Mediterranean (MED) region, a distinct part of the world, full of challenges and risks but also opportunities. Above all, the book focuses on smartening up small and medium-sized cities and insular communities, taking into account their geographical peculiarities, the pattern of MED urban settlements and the abundance of island complexes in the MED Basin. Taking for granted that sustainability in the MED is the overarching policy goal that needs to be served, the book explores different aspects of smartness in support of this goal’s achievement. In this respect, evidence from concrete smart developments adopted by forerunners in the MED region is collected and analyzed; coupled with experiences gathered from successful, non-MED, examples of smart efforts in European countries. More specifically, current research and empirical results from MED urban environments are discussed, as well as findings from or concerning other parts of the world, which are of relevance to the MED region. The book’s primary goal is to enable policymakers, planners and decision-making bodies to recognize the challenges and options available; and make to more informed policy decisions towards smart, sustainable, inclusive and resilient urban and regional futures in the MED.