Atypical in Alternative Break practice, an intentionally created connected course was examined to understand students' perceptions of their semester long experience before, during, and after their service trip. This qualitative study analyzed reflective blog posts from twenty students participating in two different Alternative Breaks. The first trip examined human environmental impact and the second explored issues of those experiencing hunger and homelessness. Two theoretical frameworks were utilized to understand how students made sense of their journey and understood diversity learning related to their trip. The course provided pre- and post-trip education related to the cause focus and to issues related to privilege, oppression, dominant narratives, and potential pitfalls related to immersive service. Findings indicate, through the reflections of students, powerful sensemaking occurred when service and learning combined in a synergistic relationship. Students connected class learning with informal interactional learning, or hands-on experiences in an immersive service environment, and stressed the importance of both in building their understanding. This research suggests that Alternative Break practitioners must 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. The results of this study may aid Alternative Break programs in creating a connected course to enhance and strengthen student learning, reflection, and sensemaking.