The purpose of this study was to explore the college choice and transfer decision-making processes of six high-achieving first-generation Latina/o transfer students who began their postsecondary studies at a community college and later transferred to a four-year Hispanic Serving Institution. Utilizing interpretative phenomenological analysis, four themes emerged from data analysis to explain the factors that influenced participants' decisions to enroll in community college: (a) Inadequate Guidance from School Personnel, (b) Financial Concerns, (c) Familial Factors, and (d) Community College as an Appropriate Match. Additionally, two themes related to the decision to transfer to a four-year institution emerged: (a) Access to Greater Opportunities, and (b) Support and Motivation. The findings of this study will aid researchers and educators alike in understanding and supporting the college choice decisions of high-achieving first-generation Latina/o students.