The Pinisi Festival, a UNESCO Intangible Cultural Heritage, serves as a vital tourism asset for Bulukumba Regency. However, the festival confronts a paradox: as a mass event, it possesses the potential to become the “antithesis of sustainability” due to its environmental impacts. A significant gap exists between the global discourse on green events and their factual implementation at the local level, which is constrained by specific socio-cultural conditions. This research aims to: (1) analyze the planning gaps in the green event concept for the Pinisi Festival; (2) diagnose the structural, managerial, and cultural barriers to its implementation; and (3) formulate a contextual solution model. Employing a qualitative case-study approach, primary data were collected via in-depth interviews with stakeholders and field observations, supplemented by secondary data. Thematic analysis was utilized to interpret the data across four key dimensions: transport management, waste management, eco-procurement, and green marketing. The findings indicate that green event implementation remains at a symbolic and partial initiation stage. This failure to apply green principles was concluded to be not merely technical; rather, it is rooted in three systemic barriers: structural (infrastructure limitations and high costs), managerial (the absence of technical regulations and binding standard operating procedures), and cultural (low compliance with pro-environmental behaviors). As its primary contribution, this research formulates a contextual transition framework. This model rests on three pillars: (1) revitalizing Local Government policy governance; (2) program innovation based on a synergy of culture and technology; and (3) capacity building for the local community and MSMEs.