The volume of the food produced across the world should be related to agricultural sustainability and is crucial for natural capital protection. Hence, sustainability assessment on farms and the identification of improvements is relevant. A mixed farm of vineyard and olive trees was chosen for sustainability assessment, based on the Best Management Practices (BMPs) that have been implemented. The aim of this research was to assess sustainability on a mixed vineyard and olive-grove farm and validate the INSPIA model for this kind of typology of a farm, which is very typical in the South of Spain. The sustainability assessment was monitored across 5-agricultural seasons based on the INSPIA methodology. INSPIA is based on the application of a set of BMPs, calculated on 31 basic indicators, providing a final composite index of sustainability. The greater the implementation of sustainable farming practices, the higher the value of the composite index. Enhanced soil, water, and air quality, improvement for biodiversity and for ecosystem services help towards sustainable agricultural productivity. Indicators’ results are shown during that period, depicting their relationship with the BMPs. The highest composite index was reached in the 4th year. This paper confirms the relevance of BMPs, such as groundcover establishment and minimum soil disturbance to upgrade sustainability on the permanent croplands in Southern Spain. The indicator-based sustainability assessment is considered a helpful tool in decision-making, which guides farmers towards BMPs performance.