This paper tells the experiences and perspectives of six exemplary elementary school principals and their teachers participating in a regional project in the Caribbean. These principals all work in difficult environments and oversee schools which had histories of academic failure. The accounts drew on a number of sources: oral presentations made by the principals in a regional forum; written reports by the principals; interviews with the principals; and questionnaire data collected from teachers from the various schools. These principals were found to possess some key qualities which make them stand out as exemplary. These include a caring attitude, discipline, supportedness, respect, facilitating collaboration, celebrating success and the ability to motivate. These qualities, cultivated and practised along with love of schools and community, helped these principals to turn their institutions around to create oases of learning, and harmonious relationships for the students, the teachers, parents and the wider community.