This study proposes a method for determining the optimal period for crop yield prediction using Sentinel-2 Vegetation Index (VI) measurements. The method operates at the single-field scale to minimize the influence of external factors, such as soil type, topography, microclimate variations, and agricultural practices, which can significantly affect yield predictions. By analyzing historical VI data, the method identifies the best time window for yield prediction for specific crops and fields. It allows adjustments for different space–time intervals, crop types, cloud probability thresholds, and variable time composites. As a practical example, this method is applied to a wheat field in the Po River Valley, Italy, using NDVI data to illustrate how the approach can be implemented. Although applied in this specific context, the method is exportable and can be adapted to various agricultural settings. A key feature of the approach is its ability to classify variable-length periods, leveraging historical Sentinel-2 VI compositions to identify the optimal window for yield prediction. If applied in regions with frequent cloud cover, the method can also identify the most effective cloud probability threshold for improving prediction accuracy. This approach provides a tool for enhancing yield forecasting over fragmented agricultural landscapes.