Dennis Roy Craig (1929–2004) was one of the most outstanding Caribbean linguists of the twentieth century. The Society of Caribbean Linguistics honoured him in 2000 for what was described as “an academic career at once awesome and inspiring”, for his devotion to Creole linguistics and his tremendous contribution to language education in the Caribbean. He was also an outstanding figure in educational leadership in the region and a poet. In this collection, eight of Craig’s most representative articles have been chosen to demonstrate his understanding of the language situation in the English-official Caribbean and the breadth of his vision in relation to the spheres of language teaching and language learning in the English-based Creole speaking societies. Although most of these articles were written between the 1970s and the 1990s, the problems and issues that they treat are what we continue to face in the twenty-first century. Language Education in the Caribbean will prove useful to language teachers, creolists, and practitioners and researchers in the field of Caribbean language education.