This study quantitatively evaluates the effectiveness of three main options for the adaptation of crop farming to climate change (i.e., shift of planting dates, increase/addition of irrigation, and resilient hybrids/cultivars) in Greece, a country in southern Europe. The potential effect of each option on the yields of several crops in all Greek regions is estimated for 2021–2040 and 2041–2060 and compared with those under the historical local climate of 1986–2005, by using agronomic and statistical regression models, and data from different climatic simulations and climate change scenarios. Our results reveal that all the adaptation options examined have the potential to significantly reduce crop yield losses occurring under no adaptation, particularly during 2021–2040 when for many regions and crops more than half of the losses can be compensated for. Notably, in some cases during this period, the measures examined resulted in crop yields that are higher than those under the historical climate. However, the effectiveness of the measures diminished significantly in 2041–2060 under very adverse climate change conditions, highlighting the dynamic nature of adaptation. Assessing the effectiveness of combined adaptation options and evaluating additional criteria (e.g., feasibility) represent essential areas for future research.