In the current information-saturated world of knowledge societies, universities are at risk of training technical experts who hold myopic views of the future, and leaders who are ill-equipped to address the systemic nature of current global ecological, economic, and political crises. In this context, and taking into account the obstacles posed, and the opportunities provided, by contemporary societies, the current paper discusses the design and implementation of courses which not only rely upon, but also increase the transformative power of Environmental Education (EE) and Education for Sustainability (EfS) within Higher Education. We rely on our experience in two college courses, in Greece and the USA, to provide reflections on the integrative, interdisciplinary and collaborative dimensions of EE/EfS and on their ability to challenge neoliberal discourse that permeates contemporary knowledge societies. The qualitative methodology utilized in the paper rests on a self-study research approach and on end-of-term course evaluations filled by the students. We propose that successful design and implementation of EE/EfS courses depends upon the instructors&rsquo / (and their institutions&rsquo / ) ability to democratize and rethink the classroom (beyond its physical limits and into the community), to help students self-examine their place in the system, and to create assignments that test the learning process rather than learning outcomes.