The enhancement of grape aroma and the investigation of the relationships between grape and wine composition are important given the growing interest in wines with distinctive varietal character. Each training system involves specific grapegrowing conditions, which affect the concentration of volatile metabolites of grape. The aim of this work was to evaluate the influence of three training systems, including little tree, bilateral Guyot, and four rays, on the volatile composition of Primitivo grape and on the volatile composition and sensory properties of the corresponding wine in Apulia region of Italy. Free and bound volatile fractions were evaluated by gas chromatography coupled to mass spectrometry. Sensory analysis was performed by a panel of trained judges. Results showed that the little tree and bilateral Guyot training systems improved the accumulation of aroma precursors and volatile compounds in grape and wine and the sensory characteristics of the wine.