Spray drift is one of the most important causes of pollution from plant protection products and it puts the health of the environment, animals, and humans at risk. There is; thus, an urgent need to develop measures for its reduction. Among the factors that affect spray drift are the weather conditions during application of spraying. The objective of this study was to develop and evaluate a spray drift evaluation tool based on an existing model by TOPPS-Prowadis to improve the process of plant protection products’ application and to mitigate spray drift for specific meteorological conditions in Greece that are determined, based on weather forecast, by reassessing the limits for wind speed and direction, temperature, and air relative humidity set in the tool. The new limits were tested by conducting experimental work in the vineyard of the Agricultural University of Athens with a trailed air-assisted sprayer for bush and tree crops, using the ISO 22866:2005 methodology. The results showed that the limits set are consistent with the values of the spray drift measured and follows the tool’s estimates of low, medium, and high risk of spray drift.