This study is based on the theoretical foundations of experiential education and on the analysis of the socio-political context of infant daycare in Portugal. The object of study is an evaluation tool for daycare (CRECHEndo), aimed at kindergarten teachers, which aims to improve the quality of educational practices. This procedural tool is the starting point for observation, reflection and curriculum planning. We present preliminary results from several case studies developed in 2013/2014, based on the monitoring of the CRECHEndo implementation by educators of two Portuguese infant daycare centers. The results show general trends in assessing the wellbeing and involvement of children and dominant themes in the analysis of the contextual factors that affect these variables. Recognizing the still shallow depth of the results, these first data suggest the potential of CRECHEndo as a support tool for reflection and planning of early childhood educators working in daycare.