Outdoor play and learning (OPL) is emphasised differently across countries, and cultural aspects influence these practices. There are ongoing debates around outdoor learning in early years, and the communication of the value, effectiveness, and applicability of OPL across schools has encountered obstacles due to various factors. The diversity of implementations within different cultures is obvious, and there are even some variations within the same country in terms of practices and understanding of the philosophy of OPL. The current case study contributes to the gap in mapping OPL practices using a comparative approach in two types of case schools in three countries: England, Greece, and Türkiye. This study offers insights from both teachers’ and head teachers’ perspectives in addition to considering observation notes. Several themes emerged from the analysis, including ‘components of schools’ daily life outdoors, forest trips and excursions, from break time to their time, and the question of training’. In conclusion, school culture and the selected educational philosophy appear to have a more significant impact on OPL practices than environmental features alone. However, the findings indicate that schools lack a strategic and systematic approach to the deployment of OPL into the school philosophy. In terms of focusing more on the outdoors, personal values play a significant role, as does the support of stakeholders. The practical similarities and differences highlighted in this study can support the development of OPL practices and inform stakeholders in the early years to reconsider their contexts and potentially introduce transformative changes.