In the vortex of the environmental and ecological crises, it is clear that the cosmopolitan way of living is facing uncertainty with no easing in sight. Looking beyond the horizon at what the aftermath will yield, it is quite clear that the meaning of urbanity has to be transformed; the urban life has to support social and ecological well-being, and the city has to intertwine more closely with nature. Therefore, wild urban woodlands (WUWs), often morphologically exclusive, culturally contradictory, and biologically heterogeneous, are recognized together with the other informal wilderness of the city as catalyzers of a newly constructed identity and the first line of defense when the question of the socio-ecological resilience of the city is raised. The present study focuses on how the biocultural diversity of WUWs can be stimulated by architecture and on which principles and restorative components an architectural design should stand on. Taking War Island on the river Danube, in the very heart of Belgrade, Serbia, as the particular case study, a specific assignment was given to students of the Faculty of Architecture in Belgrade to affirm, recuperate, and stipulate the relationship between the nature and the culture of the site. On the threshold of interdisciplinarity, a net of coordinated values is set up based on a theoretical, analytic, and typo-morphological approach, gathering the eco-cultural aspects, components, and characteristics of the place. On the bases of the students’ research-based design propositions, the results show different design paths promoting accessibility and security, restoring social responsibility and awareness, and regaining the socio-ecological well-being of the place. The conclusions drawn from the study open the perspective of the alliance between nature and culture through an architectural infrastructure that heals the landscape and induces its therapeutic properties, enhancing the biocultural diversity of the place and proclaiming a kind of hedonistic sustainability for the future life of cities.