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The main aim of this study is the in-depth analysis of perceptions, of kindergarten teachers, regarding the issue of smooth transition from kindergarten to elementary school. In detail, this research investigates the kindergarten teacher’s opinions, regarding the transition, and the factors that influence this process, documents the usual practices implemented for succeeding in this transition and, finally, investigates the in-depth analysis regarding views and practices in conjunction with demographics. The research uses quantitative methodology and implements questionnaire as a tool. 140 kindergarten teachers, stationed in public kindergartens across Greece, participated in the research. After processing the data obtained, the main hypothesis is validated and can be concluded that kindergarten teachers acknowledge the importance of smooth transition, from kindergarten to elementary school, in the development of pupils both cognitive and academically through their entire school years. According to the findings, teachers stay informed regarding this issue. The majority strongly believes that it is one of the factors contributing in the successful cooperation between teachers and pupils and also provides faster integration, of the child, to a new school environment. Findings also suggest that the teachers are fully aware of the importance of both their role and their colleagues in cooperation with the parents and home environment in general. Last, in order to ensure this transition, teachers implement several practices emphasizing those regarding open discussions, with the children, about their feelings and ambitions.