Currently, long-distance trading, gateway communities, and the longboat are understood to have emerged in the Aegean during Early Bronze (EB) IB/IIA. This longboat-trading model envisages an essentially static configuration of trading communities situated at nodal points in maritime networks of interaction, an arrangement that was brought to an end, by the beginning of EB III, with the introduction of the masted sailing ship. This article questions this EB IB/IIA emergence date and argues instead that trading, gateway communities, and the longboat have a deeper and more dynamic history stretching back at least as far as the end of the Neolithic (Final Neolithic [FN] IV). The results of recent excavations at the FN IV–Early Minoan (EM) IA coastal site of Kephala Petras in east Crete paint a picture of an early trading community that, thanks to its close Cycladic connections, enjoyed preferential access to valued raw materials, to the technologies for their transformation, and to finished objects. This monopoly over the resource of distance was in turn exploited locally and regionally in east Crete, as a social strategy, to construct advantageous relationships with other communities. FN IV–EM IA Kephala Petras thus appears to represent the earliest known of a series of Early Bronze Age gateway communities (e.g., Hagia Photia, Mochlos, Poros-Katsambas) operating along the north coast of Crete.