The sense of uncertainty and fragility due to the effects and magnitude of global challenges we are facing (from the circumstances of the pandemic to the impacts of climate change) requires—much more than in the past—the capacity to generate a visionary and forefront design approach in the young generation, with an aim to stimulate their reaction attitude rather than providing consolidated tools from past conditions that no longer exist or will rapidly evolve. Within this general framework, we have investigated the effectiveness and impacts of experienced-based methods of learning and innovative educational tools in architecture that are aimed at shaping expertise that addresses the aspects of environment and climate change in the context of socio-cultural dynamics, real potentialities and constraints, and their transdisciplinary trajectories. We analyzed five international pioneering teaching experiences that provided the opportunity to understand the outcomes of collaborative and experiential learning processes by which the educational activities leverage dialogue between diverse communities (including academia, citizens, policymakers, and practitioners). The study outcomes show that shifting the pedagogical paradigm towards experience-based models can improve the awareness of future practitioners for the climate implications of architectural design, implement their analysis and project skills, and trigger processes of knowledge transfer and co-production at the community level. Experience-based models also allow them to better address the societal and cultural issues involved in decision making.