Currently, about 50% of the world’s population is living in urban areas, and that figure is predicted to continue to increase (United Nations, Department of Economic and Social Affairs Population Division, Population Estimates and Projections Section (2009) World urbanization prospects: the 2009 revision). On the other hand, many cities are facing problems caused by urbanization. The urban heat island phenomenon, one of the urban climate problems, is a typical environmental problem encountered in dense urban areas in summer. The use of the sea breeze to mitigate the urban heat island phenomenon has attracted attention in coastal cities. Some statistics show that about 40% of the world’s population lives within 100 km of the coast (World Resources Institute, Fisheries (2007) Population within 100 km of coast). Further investigation of the environment in the urban area near the coast is, therefore, important. In this chapter, Tokyo is targeted for investigation. Tokyo is the Japanese capital, and its surrounding region, the Tokyo metropolitan area, comprises a circular area with a radius of 50 km and a population of over 30 million. Within this area, the sea breeze from Tokyo Bay is an important factor mitigating the air temperature rise in summer. However, ongoing urbanization could be changing not only the mechanism of the energy balance on the urban surface but also the sea breeze system in the region. To clarify the effects of urbanization, a mesoscale meteorological model was adopted for analysis. Simulation results suggest that expansion of the Tokyo metropolitan area from the 1970s to the 1990s has induced a temperature rise near the ground and that the difference is largest in inland areas. Moreover, the time of sea breeze penetration is delayed in suburban areas. These results suggest that the ongoing urbanization process could raise the air temperature and change the sea breeze system in the Tokyo metropolitan area.