Students with disabilities have significantly lower graduation rates in four-year postsecondary institutions than students without disabilities. Although there are many barriers associated with persistence and graduation, for students with vision loss, additional accessibility challenges exist. This paper describes a pilot study that examined the impact of a training program designed to enhance functional skills (e.g., white cane use, public transportation use, money management) that may aid in the transition to postsecondary settings. Differences in pre-/posttest results indicate statistically significant gains in functional skills reported by students and their parents, as measured by an experimental scale developed from the curriculum. Using the Snyder et al. (1991) Trait Hope Scale, "there was no statistical difference in measured pre-/posttest overall hope scores. Statistically significant relationships were found between hope scores and differences in pre/posttest student functioning," however. Given preliminary findings, this program shows promise for enhancing college readiness among high school students with vision loss.