The degradation of Italian historic centres represents an increasingly urgent issue, especially in areas where tourism pressure and uncontrolled urban growth are altering the original identity of places. The old town of Ostuni in Apulia is a clear example: the area is experiencing progressive residential decline and urban transformations that often compromise the historical legibility of the built environment. Thus, this research proposes a pilot approach that could be used as a replicable model for the entire old town. The aim is to meet contemporary needs while ensuring a balanced coexistence between the preservation of the ancient settlement and the development of the modern city. A key component is detailed urban documentation, carried out using advanced digital technologies and focused particularly on elements of historical, architectural, and artistic value. Through detailed direct and indirect analysis of existing condition, and by identifying the incompatibilities resulting from recent transformations, the research outlines potential guidelines for future interventions. These aim to preserve the identity of the place while allowing for informed and respectful development, basing on Cesare Brandi’s idea that all works of art require shared investigative criteria to guide preservation and transformation is key. Therefore, the urban environment, seen as a “collective work of art,” needs the integration of both analytical and design phases. Historical awareness becomes a fundamental element for both present and future actions. A critical knowledge-based approach is essential: it guides the planning phase through thematic analytical records, from which intervention strategies can be developed.