Concern over intergenerational ethnic continuity, with members of minority groups seeking to ensure that youth become invested in and committed to religious, cultural, or ethnic identities, is long-standing and inherent to group boundary formation. In recent years, this concern has been particularly pronounced in the North American Jewish community, with socialization and retention of Jewish young adults emerging as one of its central preoccupations. This emphasis on Jewish continuity emerged as a central concern following the legacy of experiences with anti-Semitism and discrimination. The most significant program to emerge from this agenda is Taglit-Birthright Israel, a program that has provided over 250,000 free ten-day trips to Israel for Jewish young adults from over fifty countries. Homeland tours of this sort are increasingly common across diasporic groups, and this paper attends to the emotional work that underlies collective identity formation in these tours. Through focus groups with Taglit-Birthright participants, we find that these tours engage and mobilize competing sets of emotions, and that tour members experience dimensions of closeness and distance at once. The result is that participants are engaged in a form of identity labor: they grapple with the questions of how they should affiliate as Jews, and how they can forge an identity that carves a role for themselves in the diaspora. Drawing on the sociological concept of ambivalence, we find that collective identity is successfully forged in these trips by interrupting the notion of effortless ethnic belonging, and providing participants with a deeper understanding of the commitment required for intra-ethnic group identification and attachments.