The Mediterranean landscape has been rapidly changing over the past decades. Many regions saw a population decline, which resulted in changing land use, abandonment of marginal lands and colonisation by shrubs and tree species. Typical features like farming terraces, olive yards, and upland grasslands have been decreasing over the past 50 years. This results in a declining biodiversity and loss of traditional Mediterranean landscapes. In this paper we assess the landscape changes that took place in two areas, in Portofino, on the Italian Riviera, and Lesvos, a Greek island near the Turkish coast. We compared land use maps and aerial photographs over the past decades to quantify the land use changes in these two areas. Additional information was acquired from farmers’ interviews and literature. We found that changes are related to societal changes in the appraisal of agricultural land uses, and to the urban expansion, tourism and recreation. These diffuse processes are a result of policy measures and autonomous societal transformations. This is confirmed by the results of two interview surveys: between 1999 and 2012 agricultural land use in Portofino regional Park and buffer zone further marginalised, and the associated landscape changes are perceived as a substantial loss of character and identity. This problem is emblematic for large parts of the Mediterranean. Comparing different landscapes reveal similar processes of landscape change, which can be related to similar driving forces. Based on such comparisons,we learn about possible trajectories of change, and ask for a comprehensive approach to land use management.