In the Mediterranean, field survey has been the most widely used method to detect archaeological sites in arable fields since the 1970s. Through survey, data about the state of preservation of ancient settlements have been extensively mapped by archaeologists over large rural landscapes using paper media (e.g., topographical maps) or GPS and GIS technologies. These legacy data are unique and irreplaceable for heritage management in landscape planning, territorial monitoring of cultural resources, and spatial data analysis to study past settlement patterns in academic research (especially in landscape archaeology). However, legacy data are at risk due to often improper digital curation and the dramatic land transformation that is affecting several regions. To access this vast knowledge production and allow for its dissemination, this paper presents a method based on student internships in data digitisation to review, digitise, and integrate archaeological primary survey data. A pilot study for Central–Southern Italy and the Iberian Peninsula exemplifies how the method works in practice. It is concluded that there are clear benefits for cultural resource management, academic research, and the students themselves. This method can thus help us to achieve large-scale collection, digitisation, integration, accessibility, and reuse of field survey datasets, as well as compare survey data on a supranational scale.