Anthocyanins and volatile aromas may contribute to the identity of a wine varietal. Various parameters such as terroir (including vineyard altitude), viticultural management, vinification techniques and ageing conditions can influence the physiochemical pathways of the compounds. This work evaluated the anthocyanins and volatile compounds of two monovarietal wines from indigenous varieties, Yiannoudi and Maratheftiko, grown in the island of Cyprus from the vintages 2014, 2015 and 2016. The experimental analysis comprised the determination of anthocyanin’s profile (high-performance liquid chromatography-diode array detection chromatography-electrospray ionization tandem mass spectrometry, HPLC-DAD-ESI/MS) and fermentation derived volatiles (gas chromatography-flame ionization detector, GC-FID) and a blind wine testing sensory evaluation. Both the analytical results and the blind wine tasting showed that wines, at their early stage, were easily differentiated by variety, especially in terms of anthocyanins composition, while, in aged wines, the differences among samples were influenced in time by the winemaking procedures and it was not possible to differentiate varieties in such conditions.