The urban climate is a widely studied topic by the scientific community due to its impact on the global population. The general increase in temperatures in urban environments, caused by the Urban Heat Island effect, leads to heat accumulation problems in streets and public spaces, degrading people’s outdoor experiences. Therefore, it is essential to implement effective outdoor ventilation strategies to dissipate accumulated heat and improve thermal comfort in public spaces. When designing an outdoor acclimatization strategy, it is crucial to study the inflow of external air. If the air inside the target zone is constantly being renewed, no acclimatization approach will significantly improve thermal comfort. For that reason, in this paper different wind sheltering strategies for outdoor open spaces are proposed and studied with simplified CFD models in order to measure the reduction of air renewal within a desired zone where acclimatization techniques are used. Two different approaches are being tested: the first one is based on urban canyon-like designs where the target zone is located underneath the floor level of the surroundings buildings whereas the second approach is by means of using windbreaks structures to disrupt the flow creating an isolated recirculation zone immediately after the obstacle. After defining both approaches, a 2D CFD model is created and different conditions are tested to compare which approaches reduces the incoming air, studying the streamlines pattern and the air renewal rate. After the study, it has been stated that the suggested techniques effectively reduces the air income within the desired zones, manifesting the value of this research. Finally, the main objective is to suggest methods to improve the quality of outdoor acclimatization strategies in order to recover the use of open spaces in a world climatically changing.