Traditional alcoholic beverages have always been part of the Mediterranean culture and, lately, they have been re-evaluated to valorize both the territory and local customs. In this study, the Amarena wine, a fortified wine included in the national list of the traditional agri-food products, was characterized during bottle aging for oenological parameters, chromaticity, volatiles, and inorganic elements. Then, experimental data were visually interpreted by a principal component analysis (PCA). PCA revealed that most of oenological parameters (i.e., alcoholic grade, total dry extract, sugars, organic acids, and phenolic compounds) had a scarce discriminating power. Additionally, ethyl esters were only present in younger products, while remaining at quite constant levels. Conversely, certain metals (i.e., Mg, Na, Mn, Zn, and Cu), chromatic properties, and pH differentiated older Amarena bottles from the younger counterpart. Particularly, acetaldehyde and furanic compounds proved to be valid aging markers. A sensorial analysis highlighted that fruity and floral odors and flavors characterized younger beverages, while dried fruity, nutty, and spicy notes were displayed by older products, along with the valuable attribute of “oxidized” typically observed in aged Sherry wines. Overall, this study may encourage the production and commercialization of the Amarena wine, thus preserving the cultural heritage of the Mediterranean area.