In order to interpret education – especially as it is implemented in practice – alongside with a large number of current education-related issues and problems, it is necessary to investigate the meanings of the words used in this field. Such unavoidable work of research and analysis highlights the dissonance between words and meanings that has been hypothesized – often constructed – over time and has influenced the recurring discourses on schooling, on the idea of education, of pedagogical culture and culture in general, of teaching practices and methodologies. Recurrent terms seem to have lost the deep meanings originally given to them by the auctores; much of their semantic value has faded in favour of a partiality of meaning that affects the reading and interpretation of current educational phenomena. Starting from these premises, this paper focuses on the semantic essence of such keywords as school and education as well as on the significance of the several hermeneutics of these terms in the history of Western education.