Many community colleges do not have a formal process in place to offer or support a structured gap year option for students who recently graduated from high school, thereby denying those students an educational option that has been recognized as beneficial to many learners. The purpose of this qualitative study was to explore factors that influence students' perceptions and attitudes about the gap year choice so that community college administrators can better understand how to structure and present the gap year as a viable educational option. Utilizing case studies, the researcher conducted two semi-structured interviews via Zoom with each of the study's four participants during the Fall of 2023. Each participant was a current college undergraduate student who had participated in a gap year sponsored by the college between graduating high school and beginning their freshman year of college. The families of the participants were actively involved in the decision to take a gap year, suggesting that gap year education should extend beyond students to their parents. Self-development was the primary objective for each of these students in opting for a gap year, suggesting the need for school administrators to understand the underlying driving motivators of students taking a gap year when structuring or supporting a gap year program. All participants and their families had prior positive experiences with the sponsoring school, suggesting that school affiliation plays a role in the perceived credibility of a gap year. School outreach was somewhat limited during the gap year, suggesting possible opportunities for improvement. More studies are needed to expand the body of research on this topic and to factor in how various socioeconomic and demographic conditions may impact gap year program offerings at the community college level.