The transformation of vineyard landscapes is evaluated in this article by assessing the changes in land cover and landscape diversity in selected study areas in two time periods – from 1867 to 1949, and from then to 2016. The study areas are characterised by a long history of viticulture and with important occurrences of old and new agrarian relief forms. Fine-scale land cover and landscape diversity analysis, as well as the study of historical and strategic documents, enabled an accurate interpretation of the viticultural landscape trajectories and their drivers. Landscape diversity was computed using the Shannon diversity index for each 625 square metre grid unit, and applying other metrics for the entire study area. Our research established that the study areas oscillated during this period between extensification and agricultural intensification, and the general trend confirmed the disappearance of traditional vineyards and a decline in modernised vineyard areas after socialism. Although extensification and intensification are seemingly contradictory processes, it is established that these both increase landscape diversity. In addition, landscape diversity changes in the second period are influenced more by changes in quantitative landscape pattern characteristics via edge density than qualitative patterns, e.g. patch richness, which reflect land use diversity.