Long-distance seafaring or voyaging is often understood in a traditionalist perspective that assumes particular sail and watercraft technology for which there is no physical evidence, a capability for search-and-return voyages of discovery, a degeneration of voyaging technology over time, and an isomorphism between the ethnographic and pre-European records. This chapter reviews the ethnohistoric, ethnographic, and linguistic evidence pertaining to Oceanic boats and sailing rigs and concludes that prior to about A.D. 1500 Oceanic sailing rigs were mastless without triangular sails and had no weatherly capability. This conclusion has ramifications for the explanation of the episodic nature of Oceanic colonization and post-colonization interaction.