Quality of life and well-being are hardly ever an issue when life itself is at stake. The advantages of high-quality walkable streets and public spaces are underestimated when larger problems need to be addressed first and seemingly more serious solutions need to be applied. Hence, a quantitative approach to evacuation route planning and design prevails over a qualitative one or at least a hybrid one. The scope of the ongoing study partially presented in this paper is to find methods for addressing the complicated present and the disastrous future at the same time. The one applied in the case study reported here—Susaki City in Kōchi Prefecture, Japan, which is preparing for the next Nankai earthquake and tsunami, expected sometime soon—was a cycle of active research and international workshops organized in cooperation with the local community and administration. The aim was to understand the challenges that concern the design of dual spaces that are suitable for both everyday life and emergency situations and are connected by walkable spaces. As a result, the paper offers insight into the limits of punctual treatments as well as the relativity of objective and subjective dimensions of urban walkability in the context of risk. Despite the complexity of the issue, a walkable built environment was revealed to be a countermeasure rather than a fad.