Atypical in Alternative Break (AB) practice, an intentionally connected course was examined to understand students' perceptions of their semester-long experience. Using qualitative narrative analysis, authors analyze data from 20 AB participants to evaluate student perceptions and experiential outcomes before, during, and after their service trips (one involving the social issue of human environment impact and the other, hunger and homelessness). Pre- and post-trip instruction on the causes and issues related to privilege, oppression, dominant narratives, and potential pitfalls related to immersive service is presented. Reflective blogs are measured against two theoretical frameworks: diversity learning and sensemaking. Results indicate powerful sensemaking when service and learning combine in a synergistic relationship, with students articulating the importance of class learning coupled with informal interactional learning and hands-on experience for gaining knowledge of an issue and understanding for those involved. Authors suggest that AB practitioners/faculty be diligent in preparing students to serve; thoughtful in selecting strong on-trip service experiences and community partners; mindful of the importance of reflection; and dedicated to furthering post-trip learning through sensegiving.