The purpose of this article is to present the results of a multi-site case study designed to investigate students' experiences as participants in four week-long immersion programs (New York City, Peru, the Czech Republic, Chicago). Results highlight the significance of the context of the trips and specific characteristics of the trip (e.g., getting out of the bubble, boundary crossing, and personalizing), which served as the springboard for learning and meaning making. In particular, meaning making focused on developing new understandings of social issues, privilege, and stereotypes, reframing experiences upon participants' return, and shifting sense of purpose and career planning.