In recent decades, archaeological research has provided a considerable amount of fresh data on many Hellenistic cities of Sicily, but it still lacks a comprehensive analysis, able to define peculiar urbanistic and architectural characters, chronological and spatial coordinates, as well as the historical and cultural context, abandoning the traditional interpretative paradigms. The results of our recent research in Tauromenion have allowed us to better focus on the processes related to the formation of the city and its development between III and I century B.C.; starting with a presentation of these results, we plan to offer new elements of reflection on the Sicilian Hellenistic city, discussing whether and in what it differs from the Archaic-Classical polis, first of all under the profile of the urban landscape, and what are the political, social and economic factors that underlie these processes of transformation.