Vineyards and the wine industry play a crucial role in the economy, identity, culture, and biodiversity of geographical areas. However, their resilience is increasingly threatened by climate change and other shocks affecting the entire wine supply chain, from harvesting to consumption. This project aims to develop and implement a Decision Support System (DSS) to manage risks and enhance the wine supply chain’s resilience. It focuses on mitigating operational risks in grape growing, sourcing materials, producing wine, and shipping goods. Innovative digital techniques, including IoT, Cloud Computing, and Big Data Analytics, will be utilized to gather and manage data through a unique database. Cloud platforms like Google Earth Engine will facilitate faster data processing and customized algorithm development. Simulation models will predict the impact of adverse events and help implement countermeasures. The DSS model will identify risks and select optimal intervention strategies, tested on wineries in Puglia and Campania, to ensure a sustainable and resilient wine ecosystem.