A study of the medieval and post-medieval settlements in the area of Paliochora - the region in the north of the Greek island of Kythera. Mediterranean islands, including Kythera, look both inwards and outwards. The remains of the settlement Paliochora are evidence of the failure of co-existence between the insular and the wider world between the thirteenth and sixteenth centuries on Kythera, when the settlement was in use. And the reasons for that failure can be inferred by placing the evidence in its historical context. Paliochora is, in a sense, a pirate settlement-not because it was inhabited by pirates or benefited from piracy, but because it was created, sustained and destroyed by piracy in the Aegean, especially by the climate of fear engendered by piracy.