Rice farming in Italy accounts for about 50% of the EU’s rice area and production. Precision agriculture has entered the scene to enhance sustainability, cut pollution, and ensure food security. Various studies have used remote sensing tools like satellites and drones for multispectral imaging. While Sentinel-2 is highly regarded for precision agriculture, it falls short for specific applications, like at the “Riserva San Massimo” (Gropello Cairoli, Lombardia, Northern Italy) rice farm, where irregularly shaped crops need higher resolution and frequent revisits to deal with cloud cover. A prior study that compared Sentinel-2 and the higher-resolution PlanetScope constellation for vegetative indices found a seasonal miscalibration in the Normalized Difference Vegetation Index (NDVI) and in the Normalized Difference Red Edge Index (NDRE). Dr. Agr. G.N. Rognoni, a seasoned agronomist working with this farm, stresses the importance of studying the radiometric intercalibration between the PlanetScope and Sentinel-2 vegetative indices to leverage the knowledge gained from Sentinel-2 for him to apply variable rate application (VRA). A high-resolution SkySat image, taken almost simultaneously with a pair of Sentinel-2 and PlanetScope images, offered a chance to examine if the irregular distribution of vegetation and barren land within rice fields might be a factor in the observed miscalibration. Using an unsupervised pixel-based image classification technique on SkySat imagery, it is feasible to split rice into two subclasses and intercalibrate them separately. The results indicated that combining histograms and agronomists’ expertise could confirm SkySat classification. Moreover, the uneven spatial distribution of rice does not affect the seasonal miscalibration object of past studies, which can be adjusted using the methods described here, even with images taken four days apart: the first method emphasizes accuracy using linear regression, histogram shifting, and histogram matching; whereas the second method is faster and utilizes only histogram matching.