The chapter presents new studies of a material culture, recently excavated within ancient town Akrai/Acrae, south-eastern (SE) Sicily, and shed light on the rich history of acculturation and assimilation of the local traditions with Eastern Mediterranean cultures (e.g. Greek, Aegean, Cyprus, and Levantine). The Akrai/Acrae, founded by Syracuse and being for centuries a part of Syracusan Kingdom, after the Roman conquest in 212 BC, similarly to many other Sicilian urban centres, became a part of Roman province. From the very beginning, the links with the East in this region are evident, both in the legal rules adopted here (e.g. lex Hieronica) and in the religion (e.g. cult of Cybele), but above all in the iconography and in the material culture. Many finds (e.g. pottery, terracotta figurines, glass, lamps, and jewellery), discovered within the excavations between 2009 and 2020), are an excellent confirmation of these long-distance relations throughout the town’s history. These cultural implications and imports embraced mostly the Eastern Mediterranean producers and suggest strong economic and other contacts of the population of south-eastern Sicily with the centres in the East.