Focusing on sustainability, the new Common Agricultural Policy (2023–2027) sets ambitious goals for water management, as reducing irrigation water use is a vital issue. Cooperation among farmers, relevant authorities, and researchers plays a significant role in achieving these objectives. Therefore, this study applies a multicriteria mathematical programming model to optimize land use, considering water use, profit, labor, and cost. The model was applied to three farmer groups located in Greece and proved to be valuable in the implementation of irrigation water use. Using the same methodology, two additional cases of farmer groups that utilize drylands are presented in complementary ways to investigate how the new CAP affects non-irrigated land uses. Regarding the irrigated case, reducing water usage involves decreasing the land dedicated to crops characterized by high water demand, such as rice, corn, vetch, and clover. This adjustment stems from the necessity to replace irrigated land with non-irrigated land because climate change demands low water consumption for crops and underscores the importance of the new policy framework to promote sustainable agriculture. As for the non-irrigated case, achieving optimal farm planning entails reducing the cultivated areas of vetch, grassland, and sunflower. This result is driven by the need to increase crops receiving primary subsidies, highlighting the necessity for non-irrigated farms to enhance their profitability through the benefits provided by the Common Agricultural Policy. Lastly, it is important to note that this study significantly contributes to guiding decision-makers in achieving alternative agricultural land uses and farm plans while also aiding in the comprehension of the new cross-compliance rules.