In urban areas, high air temperatures and heat stress levels greatly affect human thermal comfort and public health, with climate change further increasing the mortality risks. This study presents a high resolution (100 m) modelling method, including detailed offline radiation calculations, that is able to efficiently calculate outdoor heat stress for entire urban agglomerations for a time period spanning several months. A dedicated measurement campaign was set up to evaluate model performance, yielding satisfactory results. As an example, the modelling tool was used to assess the effectiveness of green areas and water surfaces to cool air temperatures and wet bulb globe temperatures during a typical hot day in the city of Ghent (Belgium), since the use of vegetation and water bodies are shown to be promising in mitigating the adverse effects of urban heat islands and improving thermal comfort. The results show that air temperature reduction is most profound over water surfaces during the afternoon, while open rural areas are coolest during the night. Radiation shading from trees, and to a lesser extent, from buildings, is found to be most effective in reducing wet bulb globe temperatures and improving thermal comfort during the warmest moments of the day.