The heat island effect is an important issue for large cities, especially those located in hot and moist climates. The phenomenon is more severe in urban canyons because surrounding high-rise buildings allow little ventilation and dissipation of heat caused by traffic. The primary goal of the present study is to investigate the thermal environment of a major street in Osaka by intensive measurement during the summer of 2006. Osaka is the second largest city in Japan and suffers from the most severe heat island effect. In addition, several fundamental renovations and a composite renovation for the improvement of thermal environment in the urban canyon are proposed, and the efficacies of these measures are verified by computational fluid dynamics (CFD) simulation. It was found that by modifying the heights of buildings along the street and the ground surface materials and increasing the quantity of vegetation, the thermal environment can be improved by a 2.0℃ reduction in standard new effective temperature (SET*) at maximum.