A smart sustainable city (SSC) is a paradigm that encapsulates the latest lines of development in multiple fields of research. The attempt to converge towards a model of sustainable urban life, made difficult by increasing anthropic pressure and polluting activities conducted by man, is also reflected in the intentions of public institutions to take measures of environmental risk mitigation. The change towards more liveable cities must also include the adoption of more far-reaching measures in various sectors. The objective of our work was to provide an analysis in order to assess which of the Italian provincial municipalities were most closely related to the paradigm of SSCs. This aim was pursued through a comparison based on the results of a partially non-compensatory quantitative method, known as the Pena’s Distance method (DP2). The smartest and most sustainable cities, such as Siena, Milan and Padua, were not identified on the basis of common urban characteristics but rather derived from the combination of distinctive and functional elements in the pursuit of a strategic approach aimed at fully exploiting the resources of each area. Moreover, at a macro-geographical level, from the analysis emerged the presence of contiguous clusters, i.e., areas in which a major concentration of smart sustainable municipalities tended to form.

Despite the progress of the information society, there are currently still notable differences between the access to, and usage of, information and communication technologies (ICTs) and Internet for a broad range of activities by individuals in the regions of Italy and Spain. These differences could be related to features of material and social deprivation. With 13 variables of the 40 NUTS 2 of Italy and Spain, deriving from EUROSTAT regional statistics for 2018, the aim is to respond to the following questions. Is there a relationship between the variables of ICT access and usage by households and individuals and those of social and material deprivation in the regions analysed? What is the interrelationship? Are there differences between Spanish and Italian regions in the behaviour of spatial and regional factors? Factor analysis was used to discover the relationship between variables; spatial patterns were identified by means of spatial autocorrelation; and a typology of regions has been identified by using cluster analysis. The results show that there is a relationship between the variables of ICT access and usage by households and individuals and those of deprivation in Spanish and Italian regions, and indicate that the advanced and daily use of Internet in households is negatively associated with the variables of social deprivation; and the regions with higher levels of per capita income and daily access to Internet have less employment-linked material deprivation. These results also reveal the existence of a north–south spatial pattern in both countries, and six types of regions with homogeneous characteristics have been identified.