This chapter aims to design such an inter- and transdisciplinary, multiscale and mixed method pathway to provide policy makers and stakeholders with a rationale framework of analysis for Smart Agriculture (SA) applied to the urban–rural relationships of several Italian case studies. The urban area of Pisa is situated near the coast in Tuscany and is made of a set of seven small towns. Agricultural areas in the metropolitan region are close to very urbanized and industrialized areas however, a deeply rooted rural tradition still resists. SA can be an experimental field where decision makers, civil society, academia and other actors cooperate within the proposed methodological framework to improve the urban–rural link in metropolitan regions. To date, multidisciplinary approaches on agri-urban region have mainly compared results from different disciplines regarding case study analyses. The promotion of peri-urban agriculture and rural–urban links is at the core of the pact.