In the contemporary urban planning, the outdoor comfort is more and more relevant. As a matter of fact, in some Nations the microclimate design, and so, among the others, a quantification of the outdoor comfort is already compulsory, while in many others it is recommended. Various methods to quantify the outdoor comfort can be adopted (e.g., among the others, the PMV-Predicted Mean Vote, or the PET-Physiological Equivalent Temperature), but in every formulation the quantification of the wind velocity, otherwise referred to as ventilation, close to the buildings under study is needed. In this paper, the ventilation inside and outside a group of courtyard buildings is studied via numerical simulations with ENVI-met. ENVI-met is a three-dimensional microclimate model able to simulate the ventilation in an urban environment and the interaction of air flows with surfaces of different materials, with plants and with other typical elements of the built environment in a given climate. Results highlight the relevance of the mutual influence of buildings and of their dimensions in modelling the ventilation inside and outside a courtyard.