Advances in the adoption of technological innovations represent a great driver to improve the competitiveness of the Italian extra virgin olive oil (EVOO) industry. This work assesses the efficiency of an innovative extraction plant (with low oxidative impact, heating of paste before malaxation and a special decanter that avoids the final vertical centrifugation) in terms of oil yield and quality, and economic and environmental impacts. Economic and environmental impacts were evaluated by using both life cycle costing and life cycle assessment methodologies. A sensitivity analysis was also performed to highlight the uncertain factors that may strongly affect the results. Findings showed that olive milling with the innovative plant resulted in olive oil with a significant increase in quality, although the extraction yield was significantly higher when using conventional technology. In terms of environmental results, an average growth of 4.5% of the impacts in all categories was reached. The economic results revealed the highest extraction cost for the innovative scenario as well as the lower profitability, although a positive return in investment feasibility can be achieved due to an increase in the olive oil selling price. These findings could be useful to highlight the main hotspots in EVOO production and to suggest improvements for more sustainable management.