Portugal, a leading olive oil producer, boasts six Protected Denomination of Origin (PDO) regions, with distinct olive orchard (OR) densities (traditional rainfed to super-intensive irrigated). This study aimed to assess future drought and aridity conditions and the impacts on ORs located in the PDOs. Therefore, drought and aridity indicators were considered for the historical (ERA5: 1981–2000) and future periods (2041–2060; 2081–2100), and anthropogenic forcing scenarios (RCP4.5 and RCP8.5), using a 7-member ensemble of global climate models. From Spearman’s correlation analysis, Annual Mean Aridity (AIA) was selected as the most representative indicator of the climate conditions, to which the ORs were exposed. Readily Available Soil Water (RAW; mm) was considered to represent the available soil water reservoir for olive trees. Moreover, the Olive Drought and Aridity Risk Index (ODAR) was developed to determine each OR's future risks. This index considered that the AIA and RAW were weighted by OR density fractions. In the future, southern Portugal will be more arid (0.69) than northern and central (0.60). ORs soil shows lower RAW in southern PDOs (< 60 mm) than in central and northern regions (> 90 mm). These results suggest that the south of ORs will be more exposed to water stress than the northern regions. According to ODAR, the ORs exposed to low and high risk will be mainly located in the central parts of the PDOs. In northern ORs, moderate to high risk will predominate. In the south, however, the risk will be very high, which means that the olive tree growth, fruit development, and olive oil quality could be negatively affected. Implementation of tailored adaptation measures will be required to improve the climate resiliency of the sector.