A field experiment is reported to ascertain the drift of two pesticides (chlorpyrifos and metalaxyl) in a vineyard in Italian climatic conditions and the effect of mitigation measures, such as buffer zones and tree rows, on pesticide drift contamination in a small aquatic system located inside the field. Results indicated that, in typical Italian agricultural conditions, spray drift in vineyards occurs at a distance of more than 24 m and adequate buffer zones are required to protect surface water bodies from direct contamination. The presence of tree rows in front of the water body inside the agricultural field, against the main wind direction, resulted in a very high reduction of the spray drift and of the ecotoxicological risk for aquatic ecosystem. In addition, a comparison between the data obtained in the experiment and the Drift Calculator procedure showed that the model failed when the procedure is used for short distances. However, concordance was found in terms of maximum drift distances.