Satellite technology is emerging as a promising tool for monitoring cities and cultural heritage, enabling efficient and non-invasive analysis of large areas over extended periods. In this study, we explore the potential of this method for large-scale applications, focusing on the historic centre of Pisa and its ancient city walls. Specifically, COSMO-SkyMed satellite data are used to monitor the horizontal and vertical displacements of urban walls and differential settlements in various areas of the city. The detected movements are correlated with soil morphology data and on-site evidence of cracking and deformation patterns in the structures. This approach proves to be particularly valuable for extensive linear assets such as ancient city walls, where traditional on-site monitoring can pose logistical challenges, thus aiding in the safeguarding of cultural heritage in an era of increasing environmental challenges.