<p>Based on the assumption that play is crucial to children’s development and education, especially in the early years of the schooling process, the purpose of this article is present and discuss the role of the Anjii Play in Kindergarten in the Chinese context of schooling. We conducted research that sought to describe and analyze how the Anji Play educational model can contribute to the family-school transition and to the crossing of boundaries (symbolic, physical, pedagogical, etc.). Data was collected in a kindergarten in the city of Shanghai, China. Specifically, the research sought to describe both spontaneous and guided school activities; to analyze the planned activities on students’ education; and to examine how educators plan these activities considering the process of boundary crossing, as well as how they evaluate these activities. By using the Anji Play educational method, which promotes children’s enjoyment, engagement and reflection in learning through semi-structured play with natural materials, the kindergarten seeks to implement a way of teaching that emphasizes autonomy and respect for the child. In this sense, the article focuses on the relationship between spontaneous and guided activities using the Anji Play method and their repercussions on the process of boundary crossing for the young students.</p>