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Boao is part of Track II diplomacy conducted between China and ASEAN for fostering constructivism and functionalism. Its overtly-stated objectives is to promote cooperation between states for economic development and regionalism. It is semi-institutionalized with a permanent abode in China’s Hainan Island Boao Aquapolis and its events follow a regular conference schedule. It is open and inclusive, conceptualizing itself as an international organization with global purview. This writing surveys the historical evolution of Boao as an institution and then evaluates its achievement and effectiveness over the years. An objective of this study is to ascertain if the forum is a talk shop with no effective outcomes since most of the political retirees who participate in the forum tend to carry social influences but not political influences. It highlights some achievements as counter narratives to the criticism received. There appears to be a growing link between the Chinese One Belt One Road (OBOR) initiative and the Boao Forum through the promotion of the Asian Infrastructure Investment Bank (AIIB), something first broached by the then Chief Supervisor of China Investment Corporation Jin Liqun in 2014. We may therefore likely see a growing link between the Chinese OBOR and/or AIIB engagement of ASEAN via the Nanning and Boao Platforms and overseas direct investments (economic impact) directed to ASEAN or Southeast Asian states. After examining both drawbacks and milestones, the writing will evaluate how Boao faces continuing challenges in playing a more effective role as a trade facilitator between ASEAN and China.