The effects of the spatial and temporal variability of environmental factors on viticulture are particularly important in mountainous wine regions due to their complex geomorphology. A typical example is Valtellina, an Italian valley in the middle of the Alpine chain known for its wine production. The aim of this work was to assess the effects of the current climatic conditions on Alpine viticultural production by evaluating the relationship between sugar accumulation, acid degradation, and environmental factors. To achieve this objective, a 21-year time series of ripening curves from 15 vineyards (cv Nebbiolo) along the Valtellina wine-growing belt was collected. The ripening curves were then analysed in conjunction with meteorological data to assess the influence of geographical and climatic characteristics, as well as other limiting environmental factors, on grape ripening. Valtellina is currently characterised by a stable warm phase, with yearly precipitation slightly higher than in the past. In this context, the timing of ripening and the level of total acidity are correlated with altitude, temperature, and summer thermal excess. Precipitation shows good correlations with all the maturity indices, so higher precipitation leads to late ripening and higher total acidity. Considering the oenological goal of local wineries, the results suggest that the Alpine area of Valtellina is currently facing favourable environmental conditions, with early development and increased levels of sugar while maintaining good levels of acidity.