BACKGROUND The research objectives focused on the extraction of grape tannins during extended maceration. Skins and seeds were extracted separately in a wine‐like medium. In parallel, the same grapes were fermented in industrial tanks. The content and structural characteristics of extractable proanthocyanidins (PAs) were determined spectrophotometrically and using UHPLC‐DAD‐MS/MS, respectively. Skin, seed extracts and fermented wines were characterized in chemical and sensorial terms after different extraction durations. RESULTS The extraction of high molecular‐weight PAs (HMWPs) from seeds increased for up to 20 days, whereas low molecular‐weight PAs (LMWPs) reached a plateau earlier. The extraction of HMWPs and LMWPs from skins reached a maximum at the first sampling. Sensory evaluation confirmed greater astringency and bitterness of seed extracts with increasing time. Neither seed nor skin extracts differed statistically in terms of the mean degree of polymerization (mDP) and percentage of galloylation (%G) on different extraction days (except for seeds at the first sampling). During industrial maceration, HMWPs and LMWPs increased up to 12.7% alcohol (9 days of maceration); thereafter, the increase was not significant, whereas the mDP, %G and percentage of prodelphinidins did not significantly change after 11.4% alcohol. There were positive correlations with the wine astringency and PA content. CONCLUSION Looking at both simulated and industrial maceration, it can be concluded that, with a longer maceration time, the increase in HMWP content was more evident than PA structural changes. The increasing content of tannins from seeds played an important role in the greater astringency and bitterness of Cabernet Sauvignon macerated at length. © 2019 The Authors. Journal of The Science of Food and Agriculture published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.< Réduire