In the last decades, due to climate changes, soil deterioration, and Land Use/Land Cover Changes (LULCCs), land degradation risk has become one of the most important ecological issues at the global level. Land degradation involves two interlocking systems: the natural ecosystem and the socio-economic system. The complexity of land degradation processes should be addressed using a multidisciplinary approach. Therefore, the aim of this work is to assess diachronically land degradation dynamics under changing land covers. This paper analyzes LULCCs and the parallel increase in the level of land sensitivity to degradation along the coastal belt of Sardinia (Italy), a typical Mediterranean region where human pressure affects the landscape characteristics through fires, intensive agricultural practices, land abandonment, urban sprawl, and tourism concentration. Results reveal that two factors mainly affect the level of land sensitivity to degradation in the study area: (i) land abandonment and (ii) unsustainable use of rural and peri-urban areas. Taken together, these factors represent the primary cause of the LULCCs observed in coastal Sardinia. By linking the structural features of the Mediterranean landscape with its functional land degradation dynamics over time, these results contribute to orienting policies for sustainable land management in Mediterranean coastal areas.