Children often learn about the world through exploratory play. Research shows that adults can either facilitate or impede children’s learning through exploratory play, depending on the manner in which they get involved: For example, directly instructing children what to do when facing a novel artifact may discourage them from further exploration and discovery learning (Bonawitz E, Shafto P, Gweon H, Goodman ND, Spelke E, Schulz L, Cognition 120(3):322–330, 2011. https://doi.org/10.1016/j.cognition.2010.10.001), while reframing the instruction into “pedagogical questions” may facilitate exploration (Yu Y, Landrum AR, Bonawitz E, Shafto P, Dev Sci 21(6):e12696, 2018a). How to balance between child-directed play and adult-directed instruction for optimal learning? In this chapter, I discuss the framework of guided play, which combines child autonomy with adult guidance in a playful setting (Weisberg DS, Hirsh-Pasek K, Golinkoff RM, Kittredge AK, Klahr D, Curr Dir Psychol Sci 25(3):177–182, 2016). Empirical studies suggest that guided play is effective in helping children develop numeracy, spatial, language, and literacy skills, as well as the capacity for self-directed learning. In the Singapore context, guided play shares common principles with purposeful play and iTeach recommended by the Nurturing Early Learners (NEL) framework (Ministry of Education, Nurturing early learners: a curriculum framework for kindergartens in Singapore. Ministry of Education, Singapore, 2012). It has the potential to help educators, caregivers, and policy makers create a child-friendly and purposefully designed environment that promotes exploratory learning.KeywordsGuided playExploratory playEarly childhood educationDirect instructionFree playPedagogical questions