This paper is motivated by the concept that the successful, effective, and sustainable implementation of the Smart City paradigm requires a close cooperation among researchers with different, complementary interests and, in most cases, a multidisciplinary approach. It first briefly discusses how such a multidisciplinary methodology, transversal to various disciplines such as Architecture, Computer Science, Civil engineering, Electrical, Electronic and Telecommunication engineering, Social science and Behavioral science, etc., can be successfully employed for the development of suitable modeling tools and real solutions of such socio-technical systems. Then, the paper presents some pilot projects accomplished by the authors within the framework of some major EU and national research programs, also involving the Bologna municipality and some of the key players of the Smart City industry. Each project, characterized by different and complementary approaches/modeling tools, is illustrated along with the relevant contextualization and the advancements with respect of the state of the art.