This chapter describes two related prevention interventions aimed at middle school youth that focus on an important developmental context: out-of-school or leisure time. It discusses the importance of leisure to academic success and healthy adolescent development. The chapter also defines leisure education, and describes two school-based leisure education programs. Leisure is considered to be one of the more 'free' contexts in a person's life and contains a number of health-promoting characteristics. There are two major ways leisure can contribute to educational attainment: by influencing academic achievement at school and through informal learning that occurs outside the traditional classroom. It is important to pursue cultural issues regarding leisure and leisure education for different groups. The chapter discusses the issue of implementation fidelity related to leisure education programs. It highlights that any school-based program that is out of the ordinary should be given careful attention with regard to support of teachers.