The Shimanami Kaido Expressway was visioned as a national project in the early 1970s after two tragic maritime accidents in the Setouchi Inner Sea. Since the express way connecting several islands between Hiroshima and Ehime prefecture was placed in use in 1999, it has always been a valuable means of transportation for islanders and commuters to date. In addition, with the proactive efforts made by local governments, such as Imabari City, Onomichi City, let alone with the central and prefectural governments, it has come to be acknowledged to be a sanctuary for sport cyclists. Eventually, it attracts attentions from all over Japan as a successful benchmark for both businesspeople as well as policy makers who are interested in destination management practices as part of promotion policies of reginal economies. This eventual success, however, had not been envisioned as such for a long time since the commencement of its public usage. It would rather seem that the plan had taken on its shape after a long period of many twists and turns. Furthermore, while local governments have been closely cooperating with different types of stakeholders including the actual islanders to promote the development plans, their ways of thinking are still far from unanimous. The purpose of this article is to provide business and policy students with materials that draw lessons for viewing lengthy socioeconomic processes like this case which eventually converted a nation-level, large-scale infrastructure development plan into an area-specific destination management project.