© 2019, © 2019 World Leisure Organization. The discovery of nightlife represents a major turning point in the daily lives of adolescents. It means access to a wide range of new leisure activities and places, and there is a strong symbolic value connected with the transition towards adulthood. In order to deepen the knowledge about adolescents’ nightlife, this research focused on the first nightlife experiences of young people (aged 14–16 years old) who live in the city of Barcelona (Spain). Fieldwork revealed a strong connection between urban leisure practices and leisure in the villages where many young people spend their holidays. The results focus on the role of the village as a space of confidence (both for youth and families) to explore nightlife as a testing ground for new leisure practices. The village provides social control, feelings of security and popular nightlife events (local festivals) that allow young people to start going out at night with peers. This is strongly connected to the thick social fabric of the village, where young people have important resources in terms of socio-spatial competence and social capital. At the same time, these features represent a stronger social control on the behaviour of young people and can serve as a potential restriction of their personal development. These two sides coexist in the village as a crucial testing ground for negotiating with families a more autonomous management of leisure and free time.