“Like ants or frogs around a pond,” the ancient Greeks settled along the coast of the Mediterranean Sea for access to maritime resources and transportation and communication networks (Plato Phaedo 109b). Archaeological remains of such settlements are tucked away in pockets protected by the natural topography of the undulating coastline and on promontories overlooking important sea routes. These artifacts also represent the movement of seafarers, who hopped from harbor to harbor on ships as they exchanged goods, services, and knowledge. Their repetitive movement wrote, rewrote, and overwrote patterns within the land- and seascape in a complex reciprocal process that was often echoed by and/or in response to changes in urban plans, settlement relocation, and the utility of harbors as interfaces between land and sea. In this paper, the term maritime chora is used as a tool for understanding the interconnectivity of distinct spaces and the mechanisms used to create and to formalize maritime space within the polis and the psyche of its residents. I argue that the integration between terrestrial and maritime spheres at Hellenistic Miletus brought maritime space into the territory of the Milesian polis and created a defined maritime “place,” the maritime chora. The quotidian practice of navigating on the sea visually constituted the seascape as place through the utilization of natural markers that were enhanced with manmade structures, embedding the maritime sphere with Milesian identity and memory.