Earth observation (EO) technologies and products are traditionally providing an extremely important contribution to a more efficient management of built areas and people during emergencies. Their employment could be extremely useful in monitoring and risk assessment of protected monument and sites situated in potentially vulnerable areas such as costal zones. Change detection has a crucial role in such activities, especially in case of hazardous events—on one side, this method can provide inputs in the phases of risk assessment and rapid mapping for immediate response; on the other side, over prolonged periods of time after the event, change detection can be used for purposes of option analysis of technical solutions and for overall recovery planning of the site. Workflow proposed is based on the use of Copernicus Sentinel-2 data to provide the comparison of changes occurring during extreme flooding events of river Centa, Liguria. Firstly, an investigation of NDVI and NDWI of the extreme flooding event occurring in November 2019 was conducted. The event was then put in correlation with another previously studied flooding hazard occurring in 2016 in the same area that has caused severe damages to the archaeological remains of the medieval church of San Clemente, situated within the Centa riverbed. In conclusion, the results from both years have been compared with ground truth data of topographic database in order to observe the extension of the flooded area and to provide contribution to the monitoring activities. The aim of the research was to offer some novel insight for a more informed decision-making during the risk assessment, risk management and resilience phases regarding the vulnerable built heritage sites found in coastal areas.