The Mediterranean basin has been identified as a prominent hotspot of climate change, with expected negative impacts on crop productivity, among others. Given the primary role that agriculture has to sustain cultural values, economic opportunities, and food security, it is crucial to identify specific risks in agriculture due to climate change, which can address more effective adaptation strategies and policies to cope with climate change. This study aims to evaluate the high-resolution impacts of climate change on the length of the growing cycle and yield of durum wheat, common wheat, and maize in Italy by using the CERES-Wheat and CERES-Maize crop models implemented in the Decision Support System for Agrotechnology Transfer (DSSAT) software. A digital platform (GIS-DSSAT) was developed to couple crop simulation models with dynamically downscaled climate projections at high resolution for Italy, which can better represent the Italian landscape complexity and the spatial distribution of different pedological and crop management features, providing more detailed information on the expected impacts on crops respect to previous studies at a coarser resolution. The projections have been extended for two climate change scenarios and accounting for uncertainty, either considering or not the potential direct effects of increasing atmospheric CO2 concentrations ([CO2]). Results show that climate change may affect Italian cereal production in the medium to long term periods. Maize is the main affected crop, with yield reductions homogeneously distributed from North to South Italy. Wheat yield is expected to decrease mainly in southern Italy, while northern Italy may benefit from higher precipitation regimes. Higher levels of atmospheric CO2 concentrations may partially offset the negative impact posed by climate change and increase the benefits in the northern regions, especially for common and durum wheat.