The Acropolis of Cossyra (Pantelleria) and the city of Solunto are particularly suitable for analyzing the local response to Hellenistic urbanism in the contact zone between Carthage, Syracuse and Rome. Both settlements were initially part of the Carthaginian Empire and later of the Roman province of Sicily. They were essentially shaped during the Hellenistic period, abandoned during the Roman Imperial period and never resettled. The archaeological evidence of three urban features is discussed from a comparative perspective: water management, sanctuaries, and fortifications. These elements are considered central for shaping, structuring and defining urban space, because they are a tangible expression of basic needs of urban communities. Furthermore, these elements can be seen as expressions of a common social or cultural identity. Based on these assumptions, the urban development of both sites is analyzed in order to assess how local communities responded to broader urban trends in Hellenistic Sicily.