Book excerpt: This book sheds new light on the current and future challenges faced by cities, and presents approaches, options and solutions enabled by Information and Communication Technologies (ICT) in the smart city context. By focusing on sustainability objectives within a rapidly changing social, economic, environmental and technological setting, it explores a variety of planning challenges faced by contemporary cities and the power of smart city developments in terms of providing innovative tools, approaches, methodologies and technologies to help cities cope with these challenges. Key issues addressed include smart city (e-) planning and (e-)participation; smart data management to facilitate decision-making processes in cities and insular communities on a variety of topics; smart and sustainable management aspects of climate change, water scarcity, mobility, energy, infrastructure, tourism, blue growth, risk assessment; etc. The book presents current and potential pathways and applications for the evolution of smart cities and communities, taking into consideration the unique problems and opportunities emanating from their specific geographical location. The case study examples mainly concern small and medium-sized cities and communities as well as insular areas in the Mediterranean region, while also incorporating lessons learned from other parts of the world. Their focus is on the specific opportunities and threats emerging in these urban and insular environments, which are characterized by their role as globally known tourist destinations, their coastal or port character, and unique cultural resources, as well as the high rated vulnerability in very many sustainability respects (social, economic, biodiversity, urbanization, migration, poverty, etc.) to be found in the Mediterranean region at large