This PhD research critically explores the concept of the Walkable City and the capacity for urban design and planning strategies to embrace the experiential dimensions of urban walking. In contrast to conventional approaches that view walking primarily as short-distance transportation, this thesis employs narrative and Design Driven research methodologies for examining urban settings in relation to their local walking experiences and atmospheric possibilities. Taking Prague as its primary case study, the thesis begins with a historical reading of the city fabric as walkscapes. In tandem, it traces the evolution of pedestrian infrastructures, their conceptualization and impact on urban walking practices. Central to the thesis is its positioning at the intersection of how the city, urban design, and planning are conceived, imagined, and experienced. Drawing inspiration from the historical value of trails in storytelling and landscape appreciation, this research takes an exploratory approach to tracing urban walking trails and harnesses the potency of imagination to envision walkable urban spaces. This research aims to yield insights into integrating (long-distance) urban walking within metropolitan contexts, applying narrative tools in urban design and planning strategies, and enabling architects and urban planners to address the challenges of contemporary fast-paced and digitally dominated urban lifestyles.