Rapid and extensive landscape changes have renewed interest in these landscapes’ cultural and heritage values. Efforts are underway to inventory, monitor, and evaluate landscapes to develop effective management and conservation plans, giving rise to new concepts. This study applied advanced tools such as the Maptools landscape metrics tool and GIS to map and analyse historical landscape transformations in Cartoceto, Italy. Using aerial photos from 1955, 1988 and 2019, we identified patterns and changes in landscape character, revealing significant trends in land use and ecological diversity. Our findings enhance understanding of landscape dynamics and inform conservation strategies, particularly within the European Union’s Geographical Indications scheme.