In 2019, the World Meteorological Organization published its “Guidance on Integrated Urban Hydrometeorological, Climate and Environment Services (Volume I: Concept and Methodology)” to assist WMO Members in developing and implementing the urban services that address the needs of city stakeholders in their countries. The guidance has relevant implications for not only protecting infrastructures from the impacts of climate change in the urban environment, but its proper declination strongly supports health-related policies to protect the population from direct and indirect impacts. Utilizing some principles of the guidance, the urbanized area of Bologna (Italy) was analyzed in order to furnish the municipality with tools coherent with the best practices actually emerging from the international bibliography to protect the citizens’ health of this city. Specifically, the analysis concentrated on the public spaces and the potential vulnerabilities of the fragile population to high-temperature regimes in the city. Utilizing the guidance as a methodological framework, the authors developed a methodology to define the microclimate vulnerabilities of the city and specific cards to assist the policymakers in city regeneration. Because the medieval structure of the city does not allow the application of a wide set of nature-based solutions, our main attention was placed on the possibility of furnishing the city with a great number of pocket parks obtainable from spaces actually dedicated to parking lots, thus introducing new green infrastructures in a highly deprived area in order to assure safety spaces for the fragile population.