Internal areas have become a significant topic of scientific debate due to the dynamics of depopulation that affect large parts of the country. Starting from the case study of the “Alta Tuscia Laziale - Antica Città di Castro” area, this research aimed to test the actual sustainability of the strategy endorsed by public stakeholders, based on the investment plan approved by the Cohesion Agency. A holistic sustainability assessment of the area programming was thus elaborated, comparing the transformative scenarios with the four dimensions provided by the Circle of Sustainability tool. The research objective is to establish the foundations for a continuous monitoring process to evaluate the effectiveness of the regeneration practices implemented for rural villages and support the decision-making process that guides the consequent territorial policies. The analysis highlighted an unbalanced project condition, lacking political and cultural organization.