Digital Transformation is a necessary component of territorial development processes. However, the Italian country system, characterized by small villages with a high level of protection of environmental and cultural assets, is not uniformly prepared for this transformation. While there is a recognized need for the introduction of digital innovation in terms of technology and services, a society that has not yet embraced 5.0 poses a barrier to this transformation. This document analyzes the Management Plan of a system of Municipalities in the Province of Messina, Italy, organized in a Local Action Group (LAG), (also known as GAL, Gruppo di Azione Locale in Italian), trying to understand whether the demand for territorial development is combined with a model of digital transformation. In particular, the tool created by the authors pinpointed areas to promote growth and emphasized the need to include digital technologies in the LAG’s development strategy. The findings aim to spark discussion, acknowledging that the scientific understanding of digital transformation’s impacts is still evolving. They underscore the necessity for new decision-makers actors, namely, digitally oriented governance, to lead an essential transformation that cannot be postponed.