Research work deals with the adaptation of children to start kindergarten. The aim of this paper is to describe and understand the different experiences of educators related to the course of the adaptation process and to identify different ways of implementing the adaptation process depending on the context in which the kindergarten is located and to identify opportunities and obstacles for the institution to facilitate the transition period. The departure of a child to kindergarten is considered a great event for the whole family. Adaptation is thus defined as a stressful and challenging period not only for children, but also for parents and educators. The research used a semi-structured interview method in which nine interviewees from three different kindergartens participated, differing in terms of the type of founder and the context in which they are located. Differences in adaptation processes were presented with regard to the individual characteristics of the child, with regard to the family context from which the child comes and with regard to the context of the environment in which the kindergarten as an institution for early and preschool education is located. The biggest problem appeared in the unwillingness of parents to start a child in kindergarten, which is marked by distrust of the work of the kindergarten, the work of educators as well as insufficiently developed communication with the institution in general. Insufficient information of parents about the work of kindergartens and educators is actually the reason for parental anxiety that the child eventually feels. The cooperation of all participants is very important to facilitate the course of adjustment and for the well-being of the child in general. The important role of pedagogues in the organization of the adaptation process was mostly highlighted by the difference in kindergartens that have a pedagogue, compared to one that does not.