The thirteenth-to-sixteenth-century (“Venetian”) defended settlement of Kephalos on the island of Paros was surveyed by the Cyclades Research Project (CY.RE.P.). This article offers an archaeological case-study of the kastro by examining and interpreting its medieval material remains (defensive walls, chapels, cisterns, domestic structures and surface potsherds). Moreover, on the basis of combined information from written sources and comparable building projects in late medieval Italy and the Latin-dominated Levant, more light can be shed on aspects of daily life in the Aegean. Archaeological evidence suggests that the first phase of Kephalos could be placed in the later thirteenth century but it was extended with the addition of an outer defensive wall in the late fourteenth century and was inhabited until the legendary besiege of the corsair Barbarossa in 1537. Domestic remains within the kastro suggest that the site must have been densely built, housing a large number of peasants in single-roomed two-storey houses. Architectural remains and ceramic finds on the highest point of the site testify to the existence of a strong Catholic/upper class element on the most prominent portion of the kastro, reserved for the Latin lords and their agricultural produce. Extensive survey (by CY.RE.P.) in the valley below Kephalos has shown that a number of contemporary satellite settlements existed and functioned around the kastro, suggesting an agriculturally intensified use of the rural landscape. Additionally, the study and interpretation of the surface ceramic finds offer a window to late medieval living standards and food preferences in the Aegean