Preserving our landscape in sustainable development processes is now widely considered as fundamental. It is a complex and evolving issue that can be tackled from several perspectives. Agronomy can contribute to analyzing the relationships between agricultural production systems (cropping, farming and agricultural systems) at different levels (field, farm, and region) and the agricultural landscape (in terms of patches, matrixes, dynamics, etc). This is of particular interest where the relationships between “what and how” are produced by agricultural activities and the landscape are changing. In this case their own reciprocity may represent an opportunity to analyze complex systems, such as the characterization of agri-landscapes at a regional level. We propose a case study developed as an up-scaling analytical process from a farm to a regional level. The result was the identification of six main agri-landscape systems highlighting the landscape drivers that are changing the traditional landscape of a rural region in Northern Tuscany (Lunigiana).