This essay reconstructs a complex ‘wind positioning system’ which the Ra’iātean tahu’a Tupaia shared with James Cook and select officers of his crew in 1769. It sets an array of scattered traces in the colonial archive in conversation with the more recent teachings of Te Aliki Koloso Kaveia of Taumako. The essay systematically compiles and connects evidence that Tupaia’s rua mata’i and Kaveia’s te nohoanga te matangi offered related cognitive models for navigation. Attention will be given to the ways in which signature wind positions are tied to astronomical events involving sun, moon, and star positions; how wind and astronomy provide ritualized calendrics and seasonality for voyaging; how knowledge of complex swell patterns further calibrates a multi-variable tool kit; how detailed accounts of specific island-to-island voyaging paths are built into the system; and finally how such particularities also involve primordial cosmogonic axes of (island) migration in Tahitian traditions.