An experimental investigation was performed on virgin olive oils from Coratina and Ogliarola salentina cultivars extracted from green, partially blackened and totally blackened olives in order to evaluate changes in the organoleptic properties and in the shelf-life of the oil. The aim of the investigation was to identify the optimal stage of olive maturation for each cultivar to produce higher quality oils. Routine analyses in accordance with EC regulation no. 2568/91, the determination of phenols by HPLC and induction times were carried out. On the whole, the simple phenolic compounds increased as darker olives were used whereas the hydrolysable phenolic compounds decreased. In both the cultivars, total phenols and induction times were significantly higher in the oils obtained from green olives than in oils from totally blackened olives. Hence, it seems advisable to delay olive harvesting for cultivars usually yielding bitter to pungent oils (e.g. Coratina), but to anticipate harvesting for olives producing sweet tasting oils (e.g. O. Salentina). This would produce less bitter Coratina oils, with organoleptic features which may better fulfil consumers' expectations, and O. Salentina oils more resistant to oxidation.