This chapter introduces advanced examples of workshops (WS) that have been conducted multiple times to design districts for climate change adaptation as part of area-based management activities in Japan. These activities are aimed at understanding the potential impacts of climate change on the district and generating ideas for adaptation measures, primarily emphasizing physical and environmental solutions. The themes of the WS primarily focus on heat-related measures, and the program is characterized by its use of scientific knowledge, including thermal environment measurements and simulation technologies, to understand the current situation and future challenges within the district. These WS were held a total of four times, with the first having a theme of “Inspire,” the second of “Envision,” the third of “Evaluate,” and the fourth of “Experience and Plan.” This chapter presents content on the series of WS such that urban planners can replicate it, and these examples can be widely referenced and adapted to global urban development, accounting for local characteristics.