Italy is famous for its one-of-a-kind landscapes and the many cultural heritage sites characterizing the story of its regions. In central Italy, during the medieval age, some of them were built on the top of high and steep cliffs, often on the top of ancient ruins, to protect urban agglomerations, goods and people. The geographical locations of these centers allowed them to maintain their original conformation over time, but, at the same time, exposed them to a high risk of landslides. In this context, this research aimed to present an integrated and low-cost approach to study the potential landslide phenomena affecting two medieval towns. Field surveys and mapping were carried out through the use of innovative digital mapping tools to create a digital database directly on the field. Data gathered during field surveys were integrated with GIS analyses for an improved interpretation of the geological and geomorphological features. Due to the inaccessibility of the cliffs surrounding the two villages, a more detailed analysis of these areas was performed through the use of unmanned aerial vehicle-based photogrammetry, while advanced differential synthetic aperture radar interferometry (A-DInSAR) interpretation was undertaken to verify the stability of the buildings in proximity to the cliffs and other potential active failures. The results of the study highlighted the similar geometry and structural settings of the two areas. Kinematically, the intersection of three main joint sets tends to detach blocks (sometimes in high volumes) from the cliffs. The A-DInSAR analysis demonstrated the presence of a landslide failure along the northwest side of the Monte San Martino town. The buildings in proximity to the cliffs did not show evidence of movements. More generally, this research gives insights into the pro and cons of different survey and analysis approaches and into the benefits of their procedural integration in space and in time. Overall, the procedure developed here may be applied in similar contexts in order to understand the structural features driving slopes’ instabilities and create digital databases of geological/monitoring data.