Background: Meaningful experiences are integral to well-being, yet our understanding of how educational experiences can be designed to promote meaningfulness is limited. Purpose: Our study examined whether immersion semester high schools facilitated more meaningful experiences and investigated relationships between experience factors within immersion semester high schools and meaningfulness. Method: For 3 weeks at an immersion semester high school and home, youth reported on the most meaningful activities they engaged in during morning and afternoon/evening periods, their perceived meaningfulness of that activity, the level of emotion involved, the emotional valence, and their psychological engagement and behavioral participation. We collected 18,804 observations from 638 participants and analyzed the data with a series of mixed effects models. Findings: Activities were significantly more meaningful at immersion semester high schools compared to home. Additionally, activities were more meaningful when individuals had higher behavioral participation and psychological engagement, when the experience involved more emotion, and when the emotion involved was more positive. However, interaction models indicate that the effects of psychological engagement and behavioral participation varied depending on emotional valence. Implications: To expand the reach of meaningful educational experiences, we should explore whether structural elements of immersion semester high schools can be applied to other contexts.