In this multiple case study, purposeful sampling was used to identify three participants in music education who regularly engage in travel with their secondary ensembles. The research was guided by the following questions: What is the worth and value of travel opportunities from the perspectives of the music teacher with regards to the program, the school community, and to the music education profession? What ways do the teachers feel that school ensemble travel can be improved? Data was collected by holding an individual interview with each participant, a focus group interview, and through writing prompts that each participant completed. Each traveling institution is considered a case through which to explore similarities and differences in the complexities that exist in school travel. Though peer reviewed literature is limited in this field, it is hoped that this study will expand the literature for music educators. Thus, this study is framed around research on study abroad travel and educational travel in general. Within music, a look at many of the shorter, non-academic articles from magazines for band, choral and orchestra directors draws connections between them and the data from study participants. Questioning the relevance of the tradition of ensemble travel is important given that travel occurs regularly but seems researched infrequently. Data analysis using NVivo included 29 nodes, 4 themes and word frequency statistics. A close look at the data reveals that the benefits do indeed outweigh the disadvantages of ensemble music travel because of enhanced awareness during rehearsals and many non-musical factors that prove to be a holistic factor in our music students’ education.