The exploration of crop seasonality across a region offers a way to help understand the phenological spatial patterns of complex landscapes, like agricultural ones. Knowing the role of environmental factors in influencing crop phenology patterns and processes is a key aspect for understanding the impact of climate and land use changes on agricultural landscape dynamics. We identified pixels with similar phenological behavior (i.e., pheno-clusters) and compared them to the land cover map of the study area to assess the role of the land management component in controlling the phenological patterns identified. Results demonstrated that soil texture is the most important factor for permanent crops, while large amount of rainfall and high values of available water content are the main drivers in spring cultivations (i.e., irrigated crops). Scarce water availability (in terms of soil texture, low annual precipitation and high minimum temperature) represented the main driving factor for non-irrigated crops, whose phenology is characterized by summer drought and fall-winter productivity. Compared to vegetation maps that use only land cover from a single season or period, using seasonality of the NDVI time series to classify the agricultural landscape provides different and more ecologically relevant information about croplands.