This study focuses on a specific group of sojourners that has thus far remained rather unexplored in the context of study-abroad research, namely, students with extensive prior experiences of living in, traveling to, and/or familial ties with target-language mediated communities. To this end, this study examines data obtained through episodic interviews with three American students, who grew up in close contact with German-speaking communities and studied abroad in Austria for four weeks. By means of thematic analysis, the pre-study abroad sojourn motives and reflections on sense of self, home, and belonging are contrasted with these students’ immediate and delayed post-study abroad accounts. The results shed light on both the challenges young adults grapple with due to their international biographies and the transformative effects students attribute to their short-term sojourns with regard to redefining who they are and what meaning different places of home and heritage have within their individual trajectories.