Calls for a reconnection to nature and the biosphere have been growing louder over the last decades. Cultural landscapes are rapidly changing, posing a threat to ecosystems and biodiversity, but also to human–nature connections. Human–nature connectedness may be a potential lever to shift the unsustainable trajectory that we are currently proceeding, but is also negatively influenced by it. To concretize the call for a reconnection to nature, we used the leverage points perspective on five empirical case studies with focus on human–nature connectedness. Based on the synthesis of our yearlong work, in this perspective paper, we propose four leverage points to foster a sustainability transformation: (1) maintain and enhance the structural diversity of landscapes, (2) maintain and enhance economically and ecologically sustainable small-scale agriculture, (3) strengthen sense of place and (4) strengthen sense of agency in actors. Intervening in these leverage points could be effective to foster human–nature connectedness and ultimately contribute towards a sustainable trajectory. We further argue that the interconnection between leverage points is equally important as their systemic depth.