Urban designers and planners have shown increasing interest in walkability, which not only enriches everyday life for pedestrians but also offers more opportunities for social interaction. Improving the pedestrian experience in the city improves the quality of urban life. Although we often believe that efficiency is the value that we need to pursue the most in Smart Cities, when it comes to human experience, more factors need to be considered. Most research finds that time is the most critical factor when pedestrians choose their routes. However, there is a trade-off between efficiency and experience; people may choose to walk longer to maximize their joyous experience if they only need to walk a few more minutes. It is not feasible for individuals to make a perfect decision due to the insufficient information from their own experience or navigation apps. Therefore, can we enrich the pedestrian experience by offering alternatives calculated with qualitative information? Through this research, the pedestrian’s current route choice is quantified according to how far it detours from the shortest route as a trade-off for efficiency. And the preferable route, determined by pedestrian preferences, is also suggested. This methodology allows pedestrians to choose an optimized route based on individual criteria. By offering alternatives within the existing infrastructure of the city, this research attempts to reshape the journey into a more joyous one. As a result, the journey becomes more than a way to arrive somewhere, and a destination itself.