In times of global systemic dysfunction, there is an increasing need to bridge higher education with community-based learning environments so as to generate locally relevant responses towards sustainability challenges. This can be achieved by creating and supporting so-called learning ecologies that blend informal community-based forms of learning with more formal learning found in higher education environments. The objective of this paper is to explore the levers and barriers for connecting the above forms of learning through the theory and practice of an educational approach that fully engages the heart (feelings), head (thinking), and hands (doing). First, we present the development of an educational approach called Koru, based on a methodology of transgressive action research. Second, we critically analyze how this approach was put into practice through a community-learning course on responsible tourism held in Colombia. Results show that ICT, relations to place, and intercultural communication acted as levers toward bridging forms of learning between participants, but addressing underlying power structures between participants need more attention for educational boundaries to be genuinely transgressed.