Outdoor sport-based activities can promote sustainable education and active learning in primary schools, supporting motor and cognitive development, participation, and well-being. However, evidence is limited on the role of low-specialization, adaptable outdoor activities in learning, relationships, and perceived well-being. This study examined a year-long outdoor intervention based on bocce in a natural school setting in Southern Italy. Participants were 20 children aged 9–10, including two with intellectual disabilities. Data were collected through structured and semi-structured observations (1–3 checklist, teacher notes) and repeated student questionnaires. Changes across baseline, midpoint, and follow-up were analyzed in learning processes, inclusion, socio-relational benefits, and well-being/motivation. Results showed progressive improvements in all dimensions, with early gains in learning and motivation, stable high inclusion, and gradual socio-relational growth. Bocce appears feasible, sustainable, and inclusive. Further studies with larger samples and comparative designs are needed.