The interrelations between cities, inland areas, connecting road networks, urban, and political polarities have evolved, thereby determining economic, social, and place-based impacts. Thus, via a case study of Sardinia island (Italy), this study analyses regional transport data to evaluate the interrelations and mobility issues between the main cities and the settlement geographies of internal areas with a predominantly agricultural vocation. First, it frames the problems (common to the islands) theoretically and focuses on how the internal areas (considered marginal for a long time) have considerable material and immaterial resources to be valorised. Second, the study evaluates the internal relationship networks that characterise the island territory through the cluster and principal components analysis using origin–destination data to represent vocations and population needs. A smart governance strategy is proposed for Sardinia through an assessment of the functionality of urban settlements and interconnections between the hinterlands (the small and the main cities of the case study), following the smart region paradigm. The study underlines the importance of the interconnection between urban geographical areas. Thus, given an analytical-numerical approach, the originality of this research is highlighted in how it is possible to extract social vocations of the territory, which is generally not easily quantifiable.