This study aims to propose a method for quantitatively evaluating the influence which the obstruction of sea breezes by clusters of high-rise buildings has on the urban heat island effect using a weather simulation model and Geographic Information Systems (GIS). Specifically, a method of evaluating the influence of the obstruction of sea breeze by high-rise buildings on the urban heat island effect was proposed. In the method, two scenarios that imagine urban forms which differ with regard to whether or not they contain high-rise buildings are created and weather simulation is conducted, and the results of the simulations are comparatively analyzed focusing on temperature and wind speed. Evaluation was conducted in two stages, and Shiodome of Minato City in the Tokyo Metropolis was selected as the region for evaluation. In two stages of evaluation, a rise in temperature of approximately 0.3 K and a reduction in wind speed of approximately 1 m/s were observed in a region approximately five to ten kilometers square downwind of high-rise buildings in the period 6 PM to 9 PM, and a higher temperature caused by the obstruction of sea breeze by high-rise buildings was identified. The fact that such a higher temperature was confirmed in the time period from 6 PM onwards, in which the temperature decreases, reveals that obstruction of sea breeze by high-rise buildings dulls the decrease in temperature which occurs from evening onwards, and influences nighttime urban heat island formation.