A comparative study was carried out on the volatile constituents of two brands of cigars: Antico Toscano and Toscanello. Fifty-six volatile compounds were identified using High Resolution Gas Chromatography (HRGC) and HRGC-Mass Spectrometry. The volatile fraction is mainly characterized by nitrogen compounds (24 molecules) and organic acids (15 molecules). Seventeen volatile compounds were detected only in Toscanello extracts, four of these compounds show a characteristic known aroma (butter, nuts, caramel, almond), while N-methylAcetamide was found only in Antico Toscano extracts. Three multivariate statistical techniques were used to evaluate the experimental data: Analysis of Variance (Tukey test), Cluster Analysis (CA), Principal Component Analysis (PCA). The Cluster Analysis (CA) shows the presence of two main clusters, one for each brand. The PCA confirms that the samples may be classified into two main groups on the basis of volatile compounds concentration, consistent with the grouping obtained during the CA. The Toscanello samples are characterized by alkaloids, aldehydes (caramel, almond, wood flavor), some organic acid (flower, honey, cheese), 6-methyl-5-epten-2-one and acetoin (butter). The Antico Toscano samples are characterized by pyridines, pyrazine (coconut, nut, coffee flavor) and geranylacetone (rose, magnolia flavor). Further studies, using different approaches, are in progress to determine the main odorants from the two brands of cigars.