Although summer represents an opportune time for adolescents to garner employment and community experiences that may further long-term transition goals, little is known about the expectations and needs of adolescents with disabilities during this break in the academic school year. In this article, the authors explore adolescents' perceptions about summer employment and community involvement, adult guidance, and factors that facilitate or hinder access to these experiences. They conducted focus group interviews of 16 adolescents with cognitive, emotional/behavioral, and learning disabilities from two distinct communities. Although participants held high expectations for maintaining summer jobs, they pursued work and community experiences independently and with varied success. Despite articulating low expectations for adult guidance, participants expressed a desire and/or need for mentorship or other more indirect support. By drawing on the perspectives of the adolescents themselves, the authors address (a) the value of summer as a vehicle for transition education and (b) the implications for helping teenagers secure fulfilling summer experiences. (Contains 1 table.)