In 2011 Chris Wickham highlighted the comparative potential in the post-Roman histories of Wales and southern Italy, commenting that ‘the changing societies in each were the result of indigenous developments alone.’ This chapter takes up the implicit challenge in that statement and discusses South Wales and Calabria utilizing three frames: topographical, economic, and literary. Topographically, the mountainous interiors demand attention not only as barriers to access, but also as places of refuge and retreat. Both areas were open to the sea, and potentially to hostile waterborne raiders. Economically, the two regions were unpromising for agriculture, but ideal for pastoralism, and also offered specific resources that were in demand by local elites. From a literary viewpoint, both regions generated stories that emphasized and used the landscape and followed their protagonists on journeys through and beyond the region. Whilst their development in the early Middle Ages may well have been identifiably indigenous, it did not occur in isolation from wider social and economic change.