A successful transition from home or preschool to kindergarten is a key component of school readiness. Yet, quite often this major step in a child's life is neither planned nor well coordinated. Thoughtful planning for this transition, however, can have a positive impact on children, families, teachers, schools, and communities that last well beyond the first weeks of school. There are five critical elements to be considered to ensure successful transitions for young children and their families. Elementary teachers and staff, and early education and care teachers, together with families, can make starting school a positive experience for all by focusing attention on each one of these elements: (1) Create and promote connections and relationships in the community; (2) Maintain ongoing communication; (3) Prepare children for transition; (4) Involve families in the transition; and (5) Provide program continuity through developmentally appropriate curriculum. In this article, the authors describe efforts in Hawai'i to support children's successful transition from home or preschool to kindergarten.