The growing interest in pedestrian mobility in contemporary cities poses new challenges for urban planning, especially when creating livable and walkable cities. At the same time, the rising demand for personalized tourist experiences calls for innovative solutions in designing pedestrian itineraries. This study introduces a new optimization approach that personalizes tourist routes based on individual preferences and the characteristics of the urban context. It considers not only walking times and visit duration, but also the diverse thematic utilities offered by Points of Interest (PoIs), such as historical, architectural, naturalistic, artistic, spiritual, and cultural attractions. The approach integrates tourists’ spatial and temporal needs, providing support for optimizing routes and visit schedules while considering constraints such as time and personal priorities. Furthermore, it serves as a basis for decision-support tools aimed at generating itineraries and visit plans, enhancing efficiency and tourist satisfaction, while also helping to mitigate overtourism by redistributing flows and promoting less crowded areas. The paper, including a demonstrative case study application in an urban context, tries to contribute to the broader debate on creating walkable and sustainable cities, addressing the design of urban spaces that support pedestrian mobility and encourage its conscious and optimized use, in a context that evolves with the seasons and time. The approach thus allows for the adaptation of routes to the ever-changing needs of both tourists and the city itself, supporting the planning of sustainable urban tourism that is pedestrian-friendly.