This chapter aims to understand how transitions affect children’s experiences during their early childhood years. The authors discuss the three transitions that Chilean children experience during early childhood: from home to nursery (0–3 years old), from preschool to the transition levels of early years education (4–5 years old) and from transition levels to primary education (at age 6). Acknowledging the relevance of transitions in children’s lives and the impact on their development and learning skills, the authors explore the characteristics of Chilean early childhood education (ECE) programmes, policies, and regulations to understand the ways these affect children’s experiences. Furthermore, the efforts Chilean governments have made to ease these transitions are discussed as well as the challenges that are still present in the education system to ease transitions for children.