Research into the Iron Age of Anatolia has seldom paid sufficient attention to settlement patterns and the social organization of space. The Anabasis by Xenophon records the observations of a Greek outsider who travelled across eastern Anatolia and along the Black Sea coast in 400 bce, a time that was relatively early in the colonial process in this area. Xenophon's observations are used to establish a basic model for settlement in the Black Sea coastal region of Anatolia, which is then tested against the results of recent archaeological surveys and related research on the Sinop promontory. A fuller and richer model of indigenous Iron Age settlement and colonial engagement on the Sinop promontory is developed and considered in light of recent research on colonization in the western Mediterranean and northern Black Sea regions.