At our times the gap between opportunities and practical applications of the “Smart City Concept” is very large, and the risk for Administrations is to exceed in pilots primoted by large Public Companies in order to promote their products and services regardless of the local identity and social capital. “Connected City Council” is a project of a real/virtual platform created with the goal of encouraging the promotion of the “genius loci” and the increase of “quality of life” in urban centers as a certification of “smartness”. The basic idea is to tie innovative academic research, the IT industry, SMEs and practitioners of innovation in the creation of a number of tools to be used (remotely or in presence) for the assessment and the definition of different future scenarios related to every City as a Smart City . “Connected City Council” is an online platform providing: The design of a Method of assessment for Governement, Utilities, and Organisations, according to Qualitative Criteria, based on the Gamification and Serious Game principles. A Method of Scenarios Planning, aimed to identify the development prospects for the urban areas becoming “smart”; The development of a online tool allowing stakeholders to evaluate their behaviour and their governement paths in a simple but effective methods, providing a preliminary representation of their situation. The opening of “territorial meetings” designed to meet and dialogue with stakeholders in order to share both the expressed and the latent needs, spreading the culture of smart city as a value fot the territories. The creation of an analysis tool that allows the collection of data and API in order to assess the evolution of the model. The goal is to create a network of Cities sharing their experience, reuse projects and tools, and to innovate business models related to the public administration, multi-utilities and all public and private entities lifes, creating tools that can provide a set of tools, with basic services free of charge. The aim is to enable them to have a representation of their condition compared to the theme of smartness and its sustainability. Connecting City Council is now in a beta version,, realized by 3 Italian SMEs, with the cooperation of and funded by Lombardy Region. The project aims to be in an european scale in 2015.