Digital technologies are increasingly recognised as an important aspect of early childhood education. A common pedagogical problem in early childhood education is how to most effectively integrate the provision of digital technologies in early childhood settings with play-based learning. This problem arises because of the historical emphasis early childhood education places on the use of traditional forms of play, such as role play, construction play and/or socio-dramatic play as a vehicle for supporting children’s learning. The use of technologies in early childhood education therefore tends to occur in the absence of any detailed knowledge or theorised concept of digital play. In response to this problem we have developed a new approach to observing and planning for children’s digital play called ‘web-mapping’. Web-mapping understands traditional and technological play as dialectically related and when used by educators to implement play-activities for children, suggests potential for identifying the likely characteristics of digital play. In this paper, we report on research from a current Australian Research Council Discovery Project involving educators in the use of web-mapping with children. Our focus is on describing our methodological approach in working with educators as they use web-mapping to as a basis for characterising young children’s digital play in early childhood education settings.