The production of “winter wines” in south-eastern Brazil, enabled by the double pruning technique, requires precise assessment of grape technological maturity to ensure high-quality outputs. However, conventional monitoring approaches are destructive, labor-intensive, and limited in their ability to capture vineyard spatial variability. This study aimed to develop and validate a non-destructive predictive framework for Soluble Solids (°Brix) and Titratable Acidity (TA) by integrating spatial remote sensing data with temporal agrometeorological information. Multispectral imagery was acquired via an unmanned aerial vehicle in a vineyard cultivated with Sauvignon Blanc and Syrah, from which vegetation indices were derived and combined with Growing Degree-Days to train machine learning models, including Random Forest, Multilayer Perceptron, and XGBoost. The incorporation of agrometeorological data significantly improved predictive performance compared to models based solely on vegetation indices. Among the tested algorithms, XGBoost achieved the highest accuracy, with coefficients of determination of 0.89 for °Brix and 0.77 for TA, achieved by XGBoost on an independent hold-out test set. Model interpretability analysis indicated that Growing Degree-Days and cultivar were the primary drivers of maturation dynamics, while vegetation indices refined predictions by accounting for spatial variability in plant vigor. Overall, the proposed approach represents a promising proof-of-concept framework for non-destructive maturity monitoring in precision viticulture, supporting improved monitoring of grape maturation. However, multi-season validation across diverse vineyard conditions is required to confirm its generalizability and support its application as a routine decision-support tool.