In the framework of the Call for Ideas “Climate Strategy” of the Fondazione Cariplo Ambiente 2020, the partnership comprising Comune di Brescia, Parco delle Colline, Fondazione Centro euro-Mediterraneo sui Cambiamenti Climatici (CMCC), and Ambiente Parco secured resources and support for developing the climate transition strategy of the city of Brescia through the project “Un Filo Naturale”. The project’s ambition is to implement around thirty activities to generate and enhance adaptation, mitigation, and resilience strategies for the city, as well as pursue the well-being of citizens. These activities include the implementation of multi-benefit adaptation measures in public spaces. Among the dissemination activities, some of these measures selected to reduce the risk of heatwaves, particularly tree-planting and reflective materials pavement, have been investigated to evaluate their microclimate-scale effect in terms of variations of critical parameters for thermal comfort. This study presents the main outcomes of this evaluation. In particular, a scenario-based analysis has been performed modelling the layouts before and after the potential implementation of adaptation measures in the pilot area of Via Metastasio (Brescia), using the ENVI-met computational fluid dynamics (CFD) model to quantify the potential gains of the adaptation measures and to support the communication of these benefits to the population. The comparison of these situations (ex-ante and ex-post) shows a general positive effect of the implemented measures on thermal comfort parameters.