Based on archaeological sources, this contribution considers the story of the landscape of Pantelleria Island in terms of cultural expression. The dominant factor in the human population history of the island is the complete lack of freshwater sources, a problem successfully faced since prehistory with hydro-genesis and dry-farming techniques, which is currently solved with desalination facilities. A project of archaeological survey (1996–2000) investigated the island in its entirety. The methodology of the survey, combined with the GIS spatial analyses, has made it possible to identify, in the territorial organisation between the Punic and Early Middle Age periods, an order that largely depended on the factors of location, distance, accessibility, modality, hierarchies, the scale of sites. The study demonstrates the potential of surface archaeology in terms of historic landscape knowledge, the necessary premise for its preservation and valorisation, and also as an asset for sustainability.