There has been a growing awareness of the contribution of play to the young children’s learning and development. This study aims to investigate the implement of board games play on children’s aesthetic experience and interpersonal understanding in Montessori and Constructivist classrooms. With the underlying framework follows a developmentally appropriate practice, Aesthetic Curriculum Outlines of Taiwan Education Bureau and Selman’s conceptualization of interpersonal understanding of Negotiation Strategies (NS) and Shared Experience (SE) served as the standard to collect and analyze children’s art work and play. The result is based on preschool educators’ observing and mapping during 18-week period of what children (56 children aged 60-72 month) are offered within art work and board games play, including DRECKSAU, ZICKE ZACKE, and SLEEPING QUEENS. Analytical results of children’s art work and school interviews showed difference in responsive and productive aesthetic experience in both classrooms. Analysis of NS and SE results showed a predominant use of Level 1 in both classrooms; while the Constructivist children had higher percentage and with more variety of Level 2 NS and SE. With comparison of NS and SE in friend and acquaintance pairings, there was no statistical difference in the interpersonal understanding; while there was significant difference in children’s adoption of sub-categories in Level 1 NS. In the end, the results are discussed in terms of children’s exploration and inquiry implications for early schooling educators.