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Climate change and the deriving impacts on the built environment certainly represent one of the most challenging issue for several key players involved in shaping the cities of tomorrow. This is not simply a matter of adapting buildings to new requirements, but rather to rethink the way the urban fabric reacts to new and sometimes unpredictable phenomena. The process is related to increasingly evident extreme conditions in the summer time, that strongly improve the energy demand for cooling with negative impacts on the energy balance as well as on thermal comfort conditions of the end users and of urban population with severe implication on health and wellbeing. Outdoor comfort depends on a number of inter-related factors: the characteristics of the built environment, the relationship between materials and energy use, global climate change and local micro-climate: Temperature, Solar Radiation, Wind distribution, Wind Speed, Absolute and Relative Humidity. The objective of this specific study is to test the microclimate modeling of a city portion in a demo-case – a plot of building blocks with inner courtyards – as a tool for supporting the regeneration phase addressing technological choices and design solutions to improve outdoor comfort conditions. The outcomes of the performed envi-MET simulations, comparing the situation before and after intervention, are consequently discussed. In the specific case, the developed project involving the courtyard has led the Thermal Comfort perception, evaluated in terms of PMV, to shift from “very hot” (+3.50, +4.00 red zone) and “very very hot” (above + 4.50 violet zone) to “Warm” (+1.50, +2.00) at urban plot scale.