The early 21st century is an age in which freedoms seem to expand continuously and without limits; in addition to the traditional market freedoms, there is freedom of choice related to gender, to sex, to family, to health, to life and to end of life—to name just a few domains that have embraced the ethos of individual freedom. Nonetheless, in this context of growing freedom for everybody, there is a particular freedom whose “domain” has been limited, especially in Italy: the freedom of choice related to school and education. The constraints placed upon freedom of educational choice defaults, perhaps unintentionally, to a standard orthodoxy enforced by the state and its supposedly omniscient bureaucracy. What is meant by “school choice”? It means the freedom to choose the school, the teachers, the educators, the experiences, and the educational pathways that one supposes best for one’s children, without incurring legal and economic penalties. It also means accepting that the government may regulate the system of state and non-state schools (i.e., it sets out the rules and main goals in terms of the learning and educational values with which teaching institutions should comply). Yet, to balance this, the government, except in cases of exceptional and regulated substitution according to the subsidiarity principle, may not ordinarily manage the organization and functioning of state schools and—more evidently—of non-state schools through a centralized governmental administration. These activities should be left to the individual responsibility of schools, families, companies, private investors, and the institutions of civil society. Last but not least, “school choice” means that the government bears the key responsibility of checking that schools comply with the established rules and values, and that students receive a satisfactory education, and of then making the results of those checks transparent and available for the public. This way, the government can give families very useful information that equips them to make their school choice responsibly.