Coastal flooding is an important current issue due to climate change and due to significant increases in anthropogenic pressures observed in the second half of the last century. Indeed, climate change has been causing an increase in the frequency and the intensity of various natural events such as floods and sea storms; anthropogenic pressures have caused an increase in impermeable surfaces with negative consequences on the vulnerability of territories under the action of natural events. In this paper, we analyze the effects of climate change in terms of possible increases in floodable areas and in terms of population, infrastructure, coastal dunes, and sites of social, economic, and strategic interest exposed along the coasts of the region of Calabria in southern Italy. Calabria was chosen as a case study due to its geomorphological peculiarities and its considerable anthropogenic pressures. These peculiarities cause significant variability of weather and sea conditions among the different coastal areas, which influences the coastal dynamics and the characteristics of meteorological events. The main results show that, in the analyzed areas, the floodable areas double between current and future scenarios, involving both significant percentages of the population and railways, highways, industrial areas, and coastal dunes.