This chapter details the system of early childhood and primary school education in Cyprus, focusing on transition from kindergarten to first grade. With the use of the research studies within the context of Cyprus, along with other documents including guides, policies, and curricula, we outline the processes involved in transition. Such data show that the emphasis on transition in the Greek Cypriot educational system, especially the primary school level, is not as deep as expected and reveals only sporadic attempts to examine the issue. Overall, there is lack of teacher professional training and limited assessment of actions or policies implemented in both early childhood and school institutions. We suggest systematic and combined training of kindergarten and primary school teachers stressing the necessity of research on transition to guide policies, professional development, research, and practice.