The expression “School of Toledo” typically refers to the translation work of scientific texts from Arabic into Latin, which developed in Spain between the 12th and 13th centuries. However, this label does not do justice to the great cultural significance of the phenomenon. Moreover, it has also given rise to a legend: it is indeed a popular belief that there used to be a real educational institution for translator training in Toledo, supposedly founded by Raymond, archbishop of Toledo and apparent patron of translators. Today, the hypothesis of a real school, although attractive, seems to be unreliable and not supported by the evidence. The aim of this paper is to provide – in the light of recent research – a detailed analysis of the phenomenon known as the “School of Toledo”, tracing its history between myth and reality.