This article examines an adolescent's music literacy education across Caribbean and U.S. schools using qualitative research methods and theories of multimodality, transnationalism, and global cultural flows. Findings include that the youth's music literacy practices continuously shifted in response to the cultural practices and values of the physical geographies in which he alternatively lived; however, transnational movements combined with extended physical sojourning contributed to the youth's development of progressively generative perspectives about the potential of U.S. contexts for building his music literacies and a correspondent constraining view on Caribbean geographies for his music literacy development. Amid an abundance of research on the significance of online worlds to transnational youths' identity and literacy development, this article contributes insights into how formal literacy education physically experienced within and across nations shapes the nature of literacy learning.