The aim of this study was to assess the influence of 9 winemaking technologies (traditional, delestage, saignée, delayed punching-down, addition of grape seed tannins, addition of ellagic-skin-seed tannins, heating of must-wine, cryo-maceration, and prolonged maceration) on the phenolic content and antioxidant activity of Primitivo musts and wines. Three methods for the determination of the antioxidant activity were compared: DPPH, beta-carotene bleaching assay, and ABTS. Oenological parameters and composition of the phenolic fraction of 1-y-aged wines was also determined. The addition of tannins allowed the increase of the phenolic content of musts and wines in a greater amount than the other technologies. The results concerning the antioxidant activity depended on the method applied. Concerning musts, the DPPH assay did not highlight great differences among technologies, whereas the addition of tannins allowed the obtainment of the highest antioxidant activity according to beta-carotene and ABTS assays. The wine aging determined an increase of the antioxidant activity, independently on the method applied. Wine obtained through traditional technology, saignée, and addition of tannins showed the highest antioxidant activities according to DPPH and beta-carotene. The highest correlation coefficients (0.961 and 0.932) were calculated between phenolic content and ABTS values of musts whereas the lowest values (0.413 and 0.517) were calculated between phenolic content and ABTS values of wines. Wines produced through traditional technology were the richest in anthocyanins. The addition of tannins allowed to obtain high content in monomeric anthocyanins, flavonoids, flavans reactive to vanillin, and coumaroylated malvidin and a low content in acetylated malvidin. Practical Applications: It is well known that a moderate consumption (equivalent to 2 glasses per day) of red wine is actually recommended since it appears associated with a decreased incidence of cardiovascular diseases. The mechanisms involved in this protective effect are not completely understood although they appear related to the presence of phenolic compounds. To increase the intake of these compounds without increase of the wine consumption, it is necessary to improve their extraction during maceration. This study could represent a helpful tool for wineries aimed to know the way to increase the antioxidant content of their wines, thus changing them in functional beverages and prolonging their shelf life.