The intersection between education and regional development has long been a key discourse in educational research. This study used Hainan, the second largest island in China, as a case to explore the role of education in regional repositioning, taking both the economic and cultural domains into account through the lens of history and space. Policymakers from three selected administrative areas of Hainan were interviewed. The findings suggest that regional economic structure and cultural traditions in both the past and the present together shape the provision of education in Hainan, local people's participation in education, and their education aspirations for their offspring. The people on the island view education choice through a lens of accumulated and contemporary, intergenerational economic, and cultural experiences. This study also confirms the mutual interaction of education and regional economy and culture. Education serves the region via manpower fostering and cultural mobilization. Many policies and initiatives developed to improve regional education are strategic and realistic, but local inhabitants' voices deserve to be heard and respected for better acceptance and effectiveness of policies. For education to fully play its mediating role in regional repositioning, it is necessary to locate any policies and initiatives within an analysis and full understanding of the region's complexities and specificities.