In this paper we give an overview of relevant findings of a three years long case study that was carried out in the Madeira Island, Portugal. It addresses a thirty years old project in music and drama education in primary schools, which involves all children within the school curriculum, but also in extra-curriculum activities. The study used mainly qualitative methodologies for the case study approach, and statistical analysis concerning the questionnaires that were sent out to classroom teachers, supporting teachers, and parents. Findings indicate the magnitude of the project, its educational relevance, and a strong sense of ownership and leadership as revealed both by results from the questionnaires and emerging themes in the interviews. Taking into account the contributions of activity theory, critical points were identified that may bring about a qualitative transformation capable of fostering good practices in music and drama education in primary schools in Madeira.