Greek wines excel in quality and exports, but the viticultural sector faces significant challenges from complex supply chains, shifting European policies, and the growing need for sustainability amidst climate change and economic pressures. External environmental costs could affect significantly the decision-making process of farmers, reflecting a broader evaluation of sustainability in viticulture. This study evaluates the economic and environmental impacts of organic, integrated, and conventional viticulture management systems in Drama, Greece using a life cycle (LC) approach and data envelopment analysis (DEA) to determine efficiency, quantify environmental impacts in monetary terms, and incorporate these costs into the analysis. Organic management systems have lower energy consumption and emissions compared to integrated and conventional systems, with organic systems ranging from 4546 to 6573 kWh/ha in energy use and 1358 to 1795 kg CO2 eq./ha in emissions, while integrated and conventional systems range from 9157 to 12,109 kWh/ha and 2961 to 3661 kg CO2 eq./ha. The DEA analysis reveals that most organic systems perform efficiently when accounting for environmental costs, whereas conventional systems face significant efficiency declines, with only a few maintaining optimal performance. Policy-supported transitions based on the provider gets principle are crucial for balancing economic and environmental goals in viticulture, as the integration of shadow prices significantly impacts efficiency.