With the global warming effect and the rapid growth of global urbanization, the concept of urban heat islands (UHIs) has become one of the most important environmental issues in the world. Early studies on UHIs mostly focused on highly developed, large cities and found that urban heat island intensity (UHII) can be as high as 4~7 °C. In recent years, it has also been found that the UHI of medium-sized cities can also reach 4–6 °C. Previous studies have also found that planting, street orientation, and aspect ratio individually have a great impact on the thermal environment of streets, but there are not many studies that comprehensively discuss the synergistic effects of these factors. Therefore, this study takes a tropical, medium-sized city, Chiayi City, as a case study to use the ENVI-met numerical simulation tool to comprehensively compare and analyze the influence of the trees and geometric characteristics of streets on the microclimate and comfort in the streets. As a result, in a tropical, with sea winds (west winds), medium-sized city, by comparison of 12 street schemes with different roadside tree situations (planting or not), orientations (E–W, N–S), and aspect ratios (0.3, 0.7, 1.0), the improvement benefits and possible mechanisms of air temperature, wind speed, MRT, PET, SET, absolute humidity, etc. at the pedestrian street level (H = 1.4 m) were obtained and show that the cooling effect of trees was deeply affected by the street orientation and geometry. An analysis of changes at different heights was also obtained. Finally, design strategy suggestions, such as the street orientation, should be prioritized to be parallel to the prevailing wind; modifying tree shapes or building forms on streets perpendicular to the prevailing wind for creating cool and comfortable streets in future tropical, medium-sized cities were proposed.
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