Agriculture in the Mediterranean region faces increasing challenges from climate change, including drought, soil erosion, and water scarcity. This study examines the sustainability of intensive olive farming practices, focusing on their effects on soil health, water management, and olive oil quality. Field experiments were conducted in the Messenia region of Greece, well-known for its high-quality olive oil production, to evaluate the impacts of different agricultural techniques on soil erosion and olive oil standards. Two experiments were designed: one addressing irrigation practices (rainfed, localized, and phenology-based irrigation) and the other investigating soil management strategies (herbicide use, mowing natural vegetation, and planting cover crops) on hilly terrain. In the first year, all olive oil samples met the European Commission's standards for extra virgin olive oil. Rainfed plots produced oil with lower acidity but higher peroxide values compared to irrigated plots, indicating differences in freshness and oxidation. Soil erosion data revealed significantly higher soil loss in herbicide-treated plots compared to those with cover crops or natural vegetation. These findings underscore the importance of sustainable farming practices in mitigating soil erosion and enhancing olive oil quality. Adopting such strategies is crucial for maintaining agricultural productivity and ecosystem health in the Mediterranean, especially under the pressures of climate change.