Visible-Short Wave Near Infrared (VIS + SW − NIR) spectroscopy is a real alternative to break down the next barrier in precision viticulture allowing a reliable monitoring of grape composition within the vineyard to facilitate the decision-making process dealing with grape quality sorting and harvest scheduling, for example. On-the-go spectral measurements of grape clusters were acquired in the field using a VIS + SW − NIR spectrometer, operating in the 570–990 nm spectral range, from a motorized platform moving at 5 km/h. Spectral measurements were acquired along four dates during grape ripening in 2017 on the east side of the canopy, which had been partially defoliated at cluster closure. Over the whole measuring season, a total of 144 experimental blocks were monitored, sampled and their fruit analyzed for total soluble solids (TSS), anthocyanin and total polyphenols concentrations using standard, wet chemistry reference methods. Partial Least Squares (PLS) regression was used as the algorithm for training the grape composition parameters’ prediction models. The best cross-validation and external validation (prediction) models yielded determination coefficients of cross-validation (R2cv) and prediction (R2P) of 0.92 and 0.95 for TSS, R2cv = 0.75, and R2p = 0.79 for anthocyanins, and R2cv = 0.42 and R2p = 0.43 for total polyphenols. The vineyard variability maps generated for the different dates using this technology illustrate the capability to monitor the spatiotemporal dynamics and distribution of total soluble solids, anthocyanins and total polyphenols along grape ripening in a commercial vineyard.