To be resilient to all the challenges of climate change, the urban system must decline its strategies into two types of interventions that are connected to each other: facing and resisting extreme atmospheric events thanks to specific technical interventions and activating the community to be able to adapt and react to the changes. Developing a resilient city as constituted by these aspects is the fundamental step to obtaining plans that can be truly effective in the event of a crisis. Since the end of the 20th century, different policies have been implemented to make cities and territories increasingly resilient. In particular, local administrations have been active in experimenting with good practices. This article illustrates an example of the approach of the city of Brescia (Italy) to address climate change. The administration approved a Climate Transition Strategy in June 2021 with the aim of addressing climate change through adaptation, mitigation, participation, and involvement actions. Mitigation and adaptation actions have several objectives, including reducing climate-changing emissions. The experimentation of a system of incentives for sustainable mobility, already foreseen in the existing planning with the Sustainable Urban Mobility Plan (SUMP), is part of this framework. This article aims to illustrate the ideas behind the experimentation of a reward system for the city of Brescia, investigating how to change the behavior of users, the different existing reward systems, and some examples of actual case studies. In order to change habits and create new patterns of behavior toward sustainable travel, it is considered essential to develop a reward system allowing people to have the ability, the opportunity, and the motivation to change their habits. However, this system should be supported by planning aimed at improving the efficiency, safety, and sustainability of urban mobility.