This paper provides a critical exposition and analysis of the work of an acclaimed Italian educator, Lorenzo Milani and ideas that emerged from his experiences in two Tuscan localities. His work is well known in Italy, and many parts of Southern Europe. Despite the translations of his works into English and Spanish, in the early 70s, and their use in sociology of education classes in the UK, he seems to have had a very limited impact on the Anglo-North American dominated critical education field. The paper revisits his ideas, in this 90thanniversary year, indicating their contemporary relevance and the signposts they provide for a critically and sociologically engaged pedagogy.It can be argued that there are figures from various parts of the world who can be looked up to as paragons in the field of critical education and especially critical pedagogy. Critical pedagogy is based on the belief that "education is fundamental to democracy and that no democratic society can survive without a formative culture shaped by pedagogical practices capable of creating the conditions for producing citizens who are critical, self-reflective, knowledgeable, and willing to make moral judgments and act in a socially responsible way" (Giroux, 2011, 3).Lorenzo Milani, an educator, writer and priest from Tuscany, is arguably Italy's most heralded critical pedagogue. His writings and teachings would be worth revisiting in search of signposts for a sociologically informed and critically engaged pedagogy.