Our research reframes architectural education at the intersection of cultural heritage and contemporary design challenges. Rather than approaching heritage as a backdrop or constraint, it proposes a pedagogical model that engages in, for, and through heritage by respecting its historical depth, advocating its future relevance, and using it as a medium for critical design thinking. Through theoretical investigation, historical case studies, and the development of an international design workshop in Athens, the authors demonstrate how historic or sensitive environments, such as the landscape of Plato’s Academy, offer fertile ground for promoting context-responsive, interdisciplinary, and ethically driven design approaches. The educational strategies discussed not only prepare students to engage with and reinterpret the historic environment but also empower them to create inclusive, sustainable urban spaces embedded in cultural continuity.