This thesis considers the iconography and site of the last-surviving (fragmentary) standing cross in south-west Ireland: the Kilnaruane High Cross. Overlooking Bantry Bay atop a hill in west Cork, this monument is situated within a rectilinear earth enclosure among a number of stone fragments, including four corner posts of a tomb-shrine, two bullaun stones, and a perforated pivot-stone. In addition, the following study reassesses the iconography on the north-east and south-west faces of the high cross as well as the high cross itself in light of other monumental high crosses, with a particular emphasis on its stylistic qualities, construction, and dating. The results suggest that both the iconography and location of the Kilnaruane high cross and site allude to a potential pilgrimage round located in the Bantry Bay area – situated, as it were, on the periphery of peninsular Kerry and the thriving culture of seafaring voyage in the south-west.