Cocoa farming in São Tomé and Príncipe (STP) faces several challenges due to its poor socioeconomic context, the adverse impact of climate changes, the complex and limited access to global value chains, and worldwide demand pressure for higher cocoa quality and productivity. This exploratory research investigates potential pathways to a more sustainable organic cocoa (OC) production in STP by mapping the perceptions of the stakeholders involved in its value chain. Qualitative interviews, field observation, and focus group discussions were applied to understand how sustainability dimensions, drivers, impacts, and challenges of OC are perceived and how these three dimensions can be improved and balanced. The gathered perceptions are rather diverse, reflecting the stakeholders’ position and knowledge of the specific contexts and processes. Producers do not perceive how governance is adopting new organizational structures or practices that allow for an effective sustainability improvement. Most stakeholders recognize that market-related factors drive the sustainability adoption and that financing-related constraints challenge their wide implementation. There are trade-offs and power asymmetries in the OC value chain, which manifest differently, due to the governance approaches, processes, overall regulations, and training of producers. An alignment of perceptions and activities as well as a stronger cooperation between cooperatives, private firms, and public institutions is strongly recommended.