Previous research on the Paximadi peninsula in Southern Euboea has revealed over 150 sites that were inhabited from prehistory through the modern era. This paper focuses specifically on the Classical, Hellenistic, and Roman periods, between roughly 480 BC and AD 500, when residents utilized about 20 tower structures distributed across the peninsula. Recognizing that no archaeological feature exists in isolation, the goal of this paper is to build upon previous research to situate these towers in their broader settlement context. Specifically, geographic information systems (GIS) software is used to measure the potential physical and visual connections between the Paximadi towers and other non-tower sites. This paper presents the results of line-of-sight and least-cost-path analyses to demonstrate the interconnections that may have existed from the Classical to Roman periods on Paximadi. The results are framed within a discussion of the broader interactions between Karystos and Athens.