More than a century of U.S. occupation of Hawaiʻi has given rise to multifarious forms of resistance and a range of beliefs about the future of Hawaiian sovereignty. On the north shore of Kauaʻi, the tourism industry sustains a long legacy of colonial settlement. The rising numbers of tourists, vacation homes, and landowners from the U.S. continent represent a contemporary iteration of Indigenous dispossession. For 40 years, the Waipā Foundation has fended off real estate developers to maintain the ahupuaʻa of Waipā as an outdoor classroom where youth from the region take part in cultivating ʻāina momona (abundant and fertile land). This thesis follows Waipā’s work to engage students in ʻāina stewardship, subsistence traditions, and nourishing communities across Kauaʻi. Whereas the dominative presence of the tourism industry limits the imaginability of a sovereign future, Waipā presents ways of imagining and experiencing sovereignty through its lessons on caring for land and people. Waipā’s sustained and evolving practices of relational caretaking illustrate Hawaiian sovereignty as a continual process of experimentation.