The study of geo-hydrological problems in urban contexts of considerable historical importance plays an extremely interesting role in the safeguarding of architectural and artistic assets of great value. The need to guarantee the conservation of monumental heritage is an ethical and moral requirement that new generations have a duty to support. Operating in urbanised contexts is extremely difficult, due to the presence of infrastructures and underground services that prevent the execution of classical surveys and prospecting. The technologies currently available, however, allow us to also investigate the subsoil in a non-destructive way and to control the evolution of active natural phenomena in a continuous and automated way with remote-sensing techniques. The methodological approach consists of the development of a series of cognitive investigations, aimed at identifying the elements of weakness of the soil system, so as to be able to subsequently undertake the most appropriate decisions for the reduction of geo-hydrological risks. The case here analysed concerns Lanciano city (Central Italy), famous for its pre-Roman origins, that was affected by a violent storm in the summer of 2018. This event devastated the inhabited Centre with flooding of all the neighbourhoods and the collapse of parts of buildings. For this reason, direct and indirect geognostic investigations were carried out within the Historical Centre, which is of considerable architectural value, and an important monitoring system was installed. The actual geo-hydrological hazard was planned using 3D numerical modelling to define the hydraulic and deformational behaviour of the subsoil. Comparison between the modelling performed and the monitoring data acquired has allowed us to understand the complex behaviour of the subsoil and the subsidence mechanisms of the Historic Centre.