The purpose of this constructivist case study was to investigate students’ experiences on an Alternative Spring Break (ASB) trip and the meaning students made of the experience. The research questions guiding the study were: (a) What did students learn about themselves and others through their participation; (b) How did students’ social identities interact with the contexts of the ASB immersion location and influence their experiences? In-depth data collection involved multiple sources of information, including post-trip semi-structured interviews, participant journals, and participant-observations. Data was analyzed through the constant comparison of data sources and analysis as themes emerged. Eleven participants and I traveled to Chicago during a week-long ASB experience focusing on affordable housing. Findings from this study include: (1) the intense immersion context of the trip and resulting disorientation and detachment; (2) the connections and complexities uncovered through interactions with community members, peers on the trip, and new perspectives; (3) a more complicated view of race in relation to the social issue and peer interactions; and (4) the challenges of reentry upon returning home.