This chapter presents empirical research focusing on the educational merits of outdoor risky play, centred on a play project, implemented at the Testi-Rasponi Kindergarten in the Municipality of Bologna. The project’s results aligned with existing research indicating that outdoor play experiences facilitate the release of vital energies in both children and adults, fostering enhanced self-respect, empathy towards others, and environmental consciousness. The chapter unfolds in two primary sections: first, by detailing project management and second, by presenting the project’s outcomes. Through this structure, the chapter will consider a dual perspective: while project planning adopts an adult-centric view, educational outcomes are examined from the children’s standpoint. Thus, the chapter transitions from logistical considerations such as resources, arrangements, spaces, and objectives toward reflections on the children’s perceptions, recognising them as principal stakeholders. The project execution primarily involved the head teachers, teachers of the hosting municipal Kindergarten, and experts who oversaw its implementation. We adopted a rigorous evidence-based research approach. Data collection employed an empirical Case Study design, which was deemed suitable for elucidating the educational context under scrutiny. Data analysis revealed outcomes related to well-being, socialisation, and agency, affirming that outdoor play activities effectively nurture educational needs. Ultimately, there's a call to promote risky outdoor activities, especially for individuals, including children and adults, who spend prolonged periods indoors, particularly those impacted by circumstances such as the COVID-19 pandemic or similar crises, emphasising the importance of mitigating the effects of confinement on early developmental stages.