The literature has shown a strong interest in the digitalization processes undertaken by political parties. An initial wave of studies took an exploratory approach to digital technologies, highlighting above all their communicative aspects and potential. More recently, however, the focus has shifted to how digital technologies are used and integrated from an organizational standpoint. Many of these contributions—often comparative in nature—have highlighted the determinants of using digital technologies, emphasizing the role of ideological and organizational factors (mainstream vs. challenger parties), however the subnational aspect is in our knowledge still marginal in this kind of studies. This paper aligns with that line of research, aiming to investigate how digital technologies are employed at the local level. Using Italy as a case study, the research examines the use of websites and social media by the local branches of five major Italian political parties (Fratelli d’Italia, Forza Italia, Lega, Movimento 5 Stelle, and Partito Democratico), in order to identify similarities and differences at the territorial (province) level. Analyzing the websites makes it possible to highlight the functional integration of digital technologies in carrying out organizational tasks, while examining social media activities sheds light on the nature of the communicative investment and the resulting engagement. The study also involves a series of exploratory and inferential analyses that consider contextual variables related to the level of digitalization (DESI index) and socio-political variables (electoral strongholds; sociodemographic features), aiming to determine whether and to what extent these factors explain variation in the patterns of digital technology adoption.