This paper explores the development of Shared Stories, Shared Value, a framework for cross-border cultural trails in Southeast Asia, with a focus on ASEAN collaboration. The study underscores the strategic importance of a joint multi-nation cultural tourism project for ASEAN integration, sustainable development, and shared economic growth. Adopting a qualitative approach, we synthesize literature on cultural routes, regional tourism cooperation, and case studies of ASEAN initiatives to propose a taxonomy of narrative themes mapped onto a Proposition-Capability matrix assigning complementary roles to member states. We design an accountable governance model, a regional cultural trail council with clear mandate, funding mechanisms, and decision rules, to steer these initiatives. We then present a phased pilot plan for an ASEAN cross-border cultural trail (using the Peranakan heritage as an illustrative case), along with a lightweight monitoring and evaluation toolkit. The findings highlight how shared cultural narratives can foster unity and deliver mutual value, leveraging each country’s strengths. The paper concludes with implications for ASEAN destination marketing, the role of the sharing economy in tourism, and recommendations for scaling up cultural trails across the region.