Investigation into positive youth development has led researchers to focus on the context of leisure as one that provides youth with opportunities to develop the skills and competencies desired for successful adulthood. This study surveyed 53 (14 males, 39 females, mean age 14.6) Western Australian high school students using an adapted version of the Youth Experience Survey (YES) 2.0. Participants were asked to report their perceived developmental experiences in both structured and unstructured activities across 2 domains: identity work and initiative development. Structured activities were found to offer adolescents more opportunities for the development of initiative than unstructured activities. In addition more adult involvement was found to be associated with higher levels of both identity work and initiative development experiences. No differences were found in developmental experiences between different structured activities. However comparisons among different unstructured activities suggest that some forms of unstructured leisure may be particularly beneficial to youth development Unstructured activities such as hobbies and unstructured sports offered adolescents more initiative and identity experiences than alternate unstructured activities such as media use and communication activities. Results are discussed in reference to theories of initiative development and the implications to the wider community.