Over the last few decades, there has been a growing interest in the use of cover crops (CCs) in annual rotations. CCs are a valuable tool to increase the sustainability of the agroecosystem since they offer an advantageous substitution for winter fallow. In particular, winter CCs provide many agronomic benefits and ecosystem services in arable cropping systems, for a summer crop such as tomato grown in succession. Weed suppression is one of the main benefits that could be achieved when a cover crop is included in the cropping system. The development of uncrewed aerial vehicles (UAVs) could have great potential for site-specific early and late weed monitoring, as they can combine near-real-time and low-cost approaches with high spatial, spectral and temporal resolution data. UAV’s imagery was exploited for weeds counting. The weeds within and near each strip were detected on-screen interpretation. Preliminary results revealed contrasting results about the weed detection procedures and their spatial distribution in the three investigated plots. Further analysis is necessary to refine the proposed method.