This research aims to develop educational activities during the connection period, allowing interactions to occur and the key elements of each area of expertise to be utilized. The “connection period” is the time at which five-year-old kindergarten pupils begin to prepare to move up to elementary school at the age of six. The study contained three aspects: (1) visits between kindergarten and elementary school classes were arranged, (2) elementary school teachers joined in the childcare at kindergarten, and (3) the kindergarten and elementary school teachers consulted with one another. The following three points were revealed as being important in terms of creating an environment that cultivates children’s abilities in feeling, thinking, and self-expression: (1) the relationship among the teachers, (2) the sharing of teaching materials, and (3) styles of teaching and learning. The second and the third points are connected to one another, and it is expected that the first point will lead to further improvements in the quality of the “connection period.”