The aroma profile of five premium red wines has been studied by sensory descriptive analysis, quantitative gas chromatography-olfactometry (GC-O), and chemical quantitative analysis. The most relevant findings have been confirmed by sensory analysis. Forty-five odorants, including the most intense, were identified. At least 37 odorants can be found at concentrations above their odor threshold. A satisfactory agreement between GC-O and quantitative data was obtained in most cases. Isobutyl-2-methoxypyrazine, (E)-whiskey lactone, and guaiacol were responsible for the veggie, woody, and toasted characters of the wines, respectively. The sweet-caramel notes are related to the presence of at least five compounds with flowery and sweet notes. The phenolic character can be similarly related to the presence of 12 volatile phenols. The berry fruit note of these wines is related to the additive effect of nine fruity esters. Ethanol exerts a strong suppression effect on fruitiness, whereas norisoprenoids and dimethyl sulfide enhance fruity notes.