This volume is the result of a research project that, since 2008, has had the objective of studying and understanding the spatial planning and dynamics of rural settlements located in the catchment of the River Cavadonna (south-eastern Sicily) between Late Antiquity and the Middle Ages. The new archaeological and topographical data that has emerged from recent surveys, along with a preliminary review of documentary sources and place names, together with a preliminary census of all archaeological evidence known through the scientific literature and local erudition,may contribute to a better analysis of the historical context and topographical relationships of the ancient and medieval settlements in Syracuse’s inland, and to their connection with the viability, and the peculiar geographical and strategic positions, of the ancient Greek metropolis of Syracuse and its sub-colony of Akrai.