Lugana DOC is an Italian PDO white wine from the south coast of Lake Garda, produced with ‘Trebbiano di Lugana’ grapes (synonym of ‘Trebbiano di Soave’ and ‘Verdicchio bianco’) and characterised by tropical fruit, citrus, and balsamic notes due to the presence of volatile thiols and methyl salicylate, respectively. To deepen the knowledge of the aromatic profile of these wines and to study how they evolve during aging, the chemical and sensory profile of 12 Lugana DOC wines from the same winery in different consecutive vintages (2008–2019, evaluated in 2023) were analysed. Sensory analysis data were subjected to hierarchical cluster analysis, identifying four main groups that appropriately distinguished the aged wines from the young wines. Younger wines had a greenish yellow colour and were characterised mainly by fruity, citrus, floral, and flinty notes related to thiol compound contribution. Older wines, divided into three different clusters, shifted colour towards orange and were characterised by descriptors related to oxidative aging (e.g., cooked fruit, marsala-like, figs, nuts) or retained pleasant varietal and evolutionary notes (e.g., citrus, white flowers, flint, vanilla) confirmed by their chemical markers detected by GC-MS and LC-MS.