Table grapes are harvested based on well-known maturity indices that must be monitored after fruit veraison. The aim of this study was to assess these indices across multiple locations and environmental conditions, encompassing different table grape cultivars such as Black Pearl, Crimson Seedless, Superior Seedless, and Red Globe. For this reason, grape sampling was conducted across six distinct locations characterized by varying altitudes above sea level (m asl) and environmental conditions over the ripening season. The main maturity indices, including pH, sugar content, titratable acidity, berry firmness, and other parameters were monitored over the growing season. Moreover, the quantification of total polyphenols, total anthocyanins, and antioxidant activity was determined using spectrophotometric assays at harvesting. The study has examined the effect of the vineyard’s location on grape quality and its interaction with the cultivar and environment. Crimson Seedless maintained a relatively high level of acidity with altitude near harvesting. Black Pearl exhibited a notable decline in both sugar content and berry firmness as elevation increased, whereas Red Globe demonstrated contrasting outcomes. The optimal maturity of Superior Seedless was observed at an elevation of 1000 m asl. Black Pearl and Crimson Seedless exhibited better adaptability to intermediate elevations (650 and 950 m asl), while Red Globe and Superior Seedless showed better adaptability to higher elevations (1000–1150 m asl). Among the studied cultivars, Black Pearl exhibited significantly higher levels of total polyphenols and anthocyanins, while close values were noticed between red and green cultivars.