Historical landscapes in Italy have been slowly changing over the centuries and this is because their features, once fixed into specific shapes, were perpetuated until new economic and social developments occurred. Yet, in the Alpine region, this territorial organisation underwent sudden changes after World War II (WW II), resulting in a loss in population and traditional agropastoral production in favour of skiing plants and holiday houses. Moreover, the loss of traditional knowledge pertaining to environmental behaviour has resulted in the urbanisation of lands that are vulnerable to extreme events. In turn, this has hindered sustainable urban development. Nowadays, modern mapping technologies enable the state of the landscape to be assessed before, during, and after extreme events, the increased frequency of which may be related to climate change. The case study examined in this paper is the flood that hit Limone Piemonte, Italy, between the 2nd and 3rd October 2020. On that occasion, an aerial survey of the affected areas was carried out using Uncrewed Aerial Vehicles (UAV) a few weeks after the event. Spatial analyses were also performed based on very high-resolution satellite imagery acquired a few days after the event in order to determine where to plan more detailed three-dimensional (3D) surveys. This has enabled assessments of damages at different map scales to be performed. Thanks to the availability of pre-event multitemporal cartographic reference datasets, it was possible to monitor the historical evolution of the affected areas. It was possible to assess the vulnerable areas before the event, as well as to evaluate the morphological and settlement changes after the disaster. Therefore, one of the goals of this manuscript is to demonstrate that geoinformation systems are among the primary technical tools used to analyse environmental and climatic alterations that impact landscapes. Finally, a 3D model of the affected areas was produced, fulfilling another goal of the research by providing the public administration with a sustainable and innovative tool for territorial and landscape management, in accordance with the 11th pillar of the United Nations Sustainable Development Goals (UN SDGs).