The physical nature of the built urban environment gives rise to urban heat islands (UHI), making many cities frequently thermally uncomfortable in the summer, with potentially serious effects on human health. When climate change effects of higher summer temperatures and prolonged heatwaves are factored in, it is clear that adaptive measures are needed to ensure the liveability of cities. The shade provided by planting trees is one such adaptation measure. This study, in Bolzano, Italy, used a thermal camera to record the surface temperatures of three common urban surfaces – asphalt, porphyry, and grass – in the shade of 332 single tree crowns, of 85 different species, during the peak temperature period of summer days. By comparing with the temperature of adjacent unshaded ground, estimates of the degree of surface cooling were made. Measurements at three locations within the shadow revealed higher cooling in the centre and at the western edge. The cooling was related to a multitude of tree traits, of which Leaf Area Index estimate (LAIcept) and crown width were the most important. Median average cooling of 16.4, 12.9 and 8.5 °C was seen in the western edge of the tree shade for asphalt, porphyry and grass, respectively. Maximum temperatures were reduced by roughly 19 °C for all surface types. Coniferous trees were capable of providing high cooling, however, crown dimensions may limit the receiving surface area. Descriptive and predictive multiple linear regression models were able to predict cooling with some success from several of the predictor variables (LAIcept and gap fraction). Strategic planting of single trees in cities can have significant impacts on the absorption of solar radiation by ground surface materials thus reducing the heat storage that contributes to UHIs.