Despite Xinomavro (Vitis viniferaL.) being a well-known noble red grape variety of northern Greece, little is known about its ‘‘bouquet’’ typicity. Volatile compounds of Xinomavro wines produced using a common vinification protocol were analyzed by gas chromatography–mass spectrometry and sensory descriptive analysis was carried out with a trained panel. Wines were characterized by the presence of fatty acids, ethyl and acetate esters, and alcohols, with contributions from terpenes and a volatile phenol. The most active aroma compounds were determined to be 3-methylbutyl acetate, β-damascenone, ethyl esters of octanoic and hexanoic acids, and eugenol. Those compounds positively correlated with fruity and spicy odor descriptors, with the wines being mostly characterized by five typical aroma terms: strawberry, berry fruit, spices, tomato, and green bell pepper. Partial least squares regression (PLSR) analysis was used to visualize relationship between the orthonasal sensory attributes and the volatile aroma compounds with calculated OAVs > 1. Key aroma-active volatiles in the wines were identified using GC-MS/olfactometry, providing a list of 40 compounds, among which 13 presented a modified detection frequency > 70%. This study is the first of its kind and provided strong indications regarding the aroma compounds defining the sensory characteristics of Xinomavro wines.