This essay explores the pedagogical legacy of Italian architect Giancarlo De Carlo (1919–2005), focusing on his original approach to architectural education and his conviction that the historic city can serve as a living, evolving workshop for learning. Drawing from his extensive teaching experiences—from the CIAM Summer Schools of the 1950s to the International Laboratory of Architecture and Urban Design (ILAUD)—the text examines how De Carlo’s educational philosophy was grounded in civic responsibility, interdisciplinary dialogue, and critical engagement with real urban contexts. Urbino, the Renaissance city where he worked for over five decades, emerges as both a laboratory and a pedagogical case study, central to his vision of participatory and ethical design. By integrating professional practice with academic instruction, De Carlo challenged traditional ex cathedra models and championed a collaborative, process-oriented approach to architectural education.