For many, “Hawaii” is a metonym for “paradise”: tropical sun and surf, stunning natural beauty and harmonious multicultural relations. But such touristic representations of Hawaiʻi mask a history of military invasion, occupation and dispossession of Kānaka ʻŌiwi (Native Hawaiians), ecological degradation and the savage effects of settler colonialism. This chapter considers the promise and limitations of the Hawaiʻi DeTours Project as a form of critical pedagogy for decolonial political education and transnational solidarity. After describing the Hawaiʻi DeTours Project, the chapter evaluates some of its successes and challenges, and considers whether a more decolonial tourism model can be a vehicle for advancing social and environmental justice. The chapter concludes that while a more “woke” tourism cannot promote social justice in Hawaiʻi under current conditions, huakaʻi (journeying with a purpose) to foster relationships and mutual responsibilities of care and social justice can be an effective method for political education and organising.