This paper analyzes Jewish peace organizations’ ability to advance Palestinians’ human rights through travel to the Occupied Palestinian Territories (OPT). My analysis is based on a case study of the organizational structure and pedagogical approach of Encounter, the leading tour organization bringing American Jews to the West Bank. From 2012 to 2016, I conducted 38 interviews with both tour participants and organizers, as well as 100+ hours of participant observation. Using these data, I analyze the ways that Encounter’s model contributes to and collides with the Palestinian struggle for human rights. In particular, I focus on how the organization’s strategy of appealing to mainstream Jewish leaders can perpetuate an adherence to exclusionary frameworks that enable certain human rights violations. I argue that, on the one hand, Encounter’s depoliticized emphasis on listening and thoughtful reflection facilitates transformative experiences for a wide range of Jewish leaders. Rabbis, summer camp directors, and Jewish federation heads experience increased levels of empathy and compassion towards Palestinians through Encounter’s trips. On the other hand, by working within dominant Jewish institutions, Encounter must represent Palestinians and the political content of their tours in ways that are palatable to a mainstream Jewish-American audience. This in turn enables the continuation of unequal power dynamics, stunting solidarity activism. By deconstructing this duality, I explore the limits and capabilities of travel-based peace organizations to promote social justice. On a broad level, my findings speak to the need to democratize travel and mobility. Current models of social justice tourism rely on “Westerners” undergoing a process of enlightenment that motivates privileged individuals to devote resources to the liberation of the oppressed people they meet with on their travels. Such a model for social change reinforces current economic hierarchies that enable wealthy North Americans and Europeans to expend their disposable incomes on such experiences, while forcing marginalized populations in the Global South (in this case, the Middle East) to perform political injustice and suffering for economic gain. Furthermore, individuals must perform these injustices in ways that generate income, which in turn, can distort and decontextualize their lived experiences. The result of these dynamics is that tourists’ outlets for activism are generally limited to forms of engagement that allow existing power imbalances to remain in place.