This study examines the activities conducted at the archaeological site of Aptera in Crete, Greece. The research was part of the DIACHRONIC LANDSCAPES International Design Workshop, organized by the CAM (Center for Mediterranean Architecture), TUC (Technological University of Crete School of Architecture), and UNIFE (University of Ferrara Department of Architecture). This article outlines the methods used for data acquisition and processing on a territorial scale, which generated digital outputs necessary for the analysis and design phases of the workshop, as well as for further examination of the results. The collected data, obtained through low-cost aerial photogrammetric surveying and GNSS terrestrial coordinate detection, were integrated in a Structure from Motion workflow that led to the creation and exportation of various digital outputs, such as point clouds, DTM, DSM, orthophotos, and contour lines. An accuracy analysis was performed to evaluate the effectiveness and efficiency of the digital models compared to the implemented surveying strategies, including the Ground Control Point and Quality Check Point marker positioning strategy. The resulting digital models proved to be valuable assets for analysis and design within the workshop and provided insightful prospects for future research and territorial-scale projects.