Urban air mobility operations, such as flying Uncrewed Aerial Vehicles (UAVs) and small passenger aircraft in and around cities, will be inherently susceptible to the turbulent wind conditions in urban environments. Therefore, understanding UAM aircraft performance under microscale wind disturbances is critical. Gaining such insight is non-trivial due to the lack of sufficient UAM aircraft operational data and the complexities involved in flight testing UAM aircraft. A viable solution to overcome this hindrance is through simulation-based flight testing, data collection, and performance assessment. To support this effort, the present paper establishes a custom Stochastic microscale Wind Model (SWM) capable of efficiently generating high-resolution, spatio-temporally varying urban wind fields. The SWM is validated against wind tunnel test data, and subsequently, the findings are employed to guide targeted refinements of urban wake simulation. Furthermore, to incorporate realistic atmospheric conditions and demonstrate the ability to generate location-specific wind fields, the SWM is coupled with the mesoscale Weather Research and Forecasting (WRF) model. This integrated approach is demonstrated through a case study focused on a potential vertiport site in Milan, Italy, illustrating its utility for assessing operational area-specific UAM aircraft performance and vertiport emplacement.