Coastal erosion coupled with human-induced pressure has severely affected the coastal areas of the Mediterranean region in the past and continues to do so with increasing intensity today. In this context, the Pisa coastal plain shows a long history of erosion, which started at the beginning of the nineteenth century. In this work, shoreline positions derived from historical maps as well as airborne and DGPS (Differential Global Positioning System) surveys were analyzed in a GIS (Geographic Information System) environment to identify the main changes that have occurred in the last 142 years. These analyses were compared with 100 years of discharge data measured at the S. Giovanni alla Vena gauge to identify a possible correlation between the two sets of information. Finally, Sentinel-2 and Landsat images were studied to identify the dispersion of sediments transported by the Arno River. In particular, we found a minimum of fluvial discharge in the years 1954, 1978, and 2012 corresponding to a peak of erosion, while the reduced erosion rate and the fluvial discharge increased in the years 1928–1944, 1954–1975, and after 2012. The qualitative anticorrelation between discharge and erosion is particularly true if we take into account flood events with a value of discharge greater than 700 m3/s, which are those able to transport suspended sand. The remote sensing analyses of Sentinel-2 images acquired during the floods of 6 February 2019 and 3 December 2019, under the most typical wind and sea state conditions for this area (wind coming from SW and storms coming from W/SW and SW) show that during these events a consistent amount of sediment was transported by the river. However, the majority of these sediments are not deposited along the coastline but are dispersed offshore. Grain-size analyses on the transported sediment show that plumes are formed by coarse-to-medium sand, suitable for coastal nourishment, but the reconstructed sediment dispersion lines show that some sectors of the coastline are constantly in the shade. These areas are the most affected by erosion.