Although Strabo provides lengthy accounts of Troy and Rome in the Geography, the role of these cities in his geographical thinking has received little attention from scholars. This article argues that for Strabo, Rome and Troy serve as exemplars of the progression of human civilization from Homeric prehistory to the Augustan present. They are paradigmatic “rising” and “fallen” cities, through which the lifecycles of all cities in the oikoumenē can be understood. Moreover, in his treatment of the fall of Troy and the rise of Rome, Strabo departs from his Augustan-era contemporaries by emphasizing the historical interactions of each city with its respective region, rather than Rome’s purported Trojan origins. In describing Rome’s expansion into Latium (Book Five) and the post-Trojan War history of the Troad (Book Thirteen), Strabo emphasizes the mutability of urban landscapes through the destruction of existing cities and the creation of new ones – two processes in which Rome has played a significant role, and which continue to shape human settlement across the oikoumenē.