The experience of the COVID-19 pandemic brought about fundamental changes in the relationship between people and their cities. The pandemic also unveiled design elements in public spaces that were previously not visible. This study draws on these elements to investigate some of the implications that the design in public spaces will have in relation to the well-being of the community. The study analyses three regions shown in both historical and contemporary contexts, resulting in some of the design principles at stake. Epidemics bring specific factors into view regarding disease transmission. In the case of respiratory diseases such as COVID-19, physical space is a critical element in the way of transmission; in this context, urban design takes on a medical dimension. Taking this into account, the analysis of these case studies addresses several important points, including behaviour within the public space, density management, and current design strategies for the future of these cities. The research identifies the need for new urban outdoor lifestyles. The principles derived from the analysis of the case studies suggest that a network of parks, small squares, and greenspaces could provide a more active and balanced lifestyle for many people than most of the current urban designs allow. Using speculative design strategies, the research develops three cartographic propositions regarding a new network of interconnected greenspaces in three example cities. These maps are intended to provoke imagination and encourage the reconsideration of the city that maintains a universal well-being.