In this article, we present our development of a virtual reality simulation of sailing on the Hōkūle‘a, a Polynesian double-hulled sailing canoe built in Hawai‘i in 1974, which completed its worldwide journey in 2017. The construction and sailing of this vessel is of significant importance to the Hawaiian cultural renaissance of the 1970s and 1980s; of particular relevance is Hawaiian wayfinding, the cultural practice of navigating across the open ocean to a destination without the use of maps or modern navigation instruments. By developing the simulation, we aimed to assist in the cultural preservation of the star navigation portion of Hawaiian wayfinding techniques, and to help to educate future generations of non-instrument navigators. The first implementation of Kilo Hōkū as a cultural heritage project in virtual reality was to test its viability as a tool for Modern Hawaiian wayfinders to use in classroom instruction, and its realism as an accurate reproduction of the Hōkūle‘a’s sailing experience. The reaction to the simulation from current practicing Modern Hawaiian wayfinders was positive, and indicates that further study is warranted in testing the efficacy of the simulation for teaching Hawaiian wayfinding to future navigators, as well as preserving and spreading knowledge of Hōkūle‘a and of Modern Hawaiian wayfinding beyond Hawai‘i.