Traditional narratives of Eastern Mediterranean prehistory regard the Mediterranean Sea as a barrier to human movement and interaction until very recently in human history. This talk summarizes available data from the deep human past to the start of the Neolithic to address notions of isolation and marginality in the Mediterranean. Material evidence from the region’s islands is brought together to discuss prehistoric maritime capabilities and socio-cultural developments. With a particular focus on Cyprus, the island’s position in the wider Eastern Mediterranean socialscape is considered. The discussion highlights early human ability for long-distance maritime interactions and firmly establishes the Mediterranean Sea as a connecting medium between distant communities, thus, rejecting outdated views of presumed sea barriers and insular marginality.