From the analysis on the industrial and urban development contexts of Kaohsiung City, it is clearly shown that the transformation and regeneration of traditional industries of Kaohsiung are unavoidable and imperative. Cultural creative industry is an important direction for industry regeneration. The cultural creative industry of Kaohsiung City can be focused on five main directions: oceanic, logistic, heavy chemical industrial, performative, and audio-visual. According to the results of in-depth analysis made by the study on the cultural creative industries and cultural creative urban resources of Kaohsiung County and Pingtung County, four characteristics of cultural resources can be summed up. Based on these characteristics, the main development of cultural creative industries in Kaohsiung County and Pingtung County can be positioned at the contents of three major cultural creative industries, including ethnic, agricultural and fishing, and oceanic. In summary, Kaohsiung City can serve as a core cultural creative city in Kaohsiung-Pingtung area. Both Kaohsiung County and Pingtung County can serve as a hinterland with very rich original cultural source materials and assets. It is expected that they can be effectively integrated as a cultural creative urban system in the form of metropolis, and can further expand the output value of cultural creative industry. Moreover, surveys and focused informal discussions with experts and scholars by Delphi method were made. The study synthesizes and summarizes four facets, including social and cultural environment, urban environment, technological innovation, diversification and human resources, as well as 26 indicators which are suitable for the development and construction of cultural creative cities in the Kaohsiung-Pingtung area. According to these 26 indicators and the current development of the Kaohsiung-Pingtung area, the study also calculates the indicator values of these three cities and makes rating of the indicators. It reflects the obvious relationship among the constructed core, frontier and hinterland of the cultural creative cities. Finally, the study proposes five specific strategic plans for promoting the Kaohsiung-Pingtung area to be developed as cultural creative cities.