There is substantial variation in levels of extractable phenolic compounds of red grapes (Vitis vinifera L.). Therefore, it could be desirable to known the aforesaid parameter at least for each vine. Nowadays, interest has shifted toward the development of portable vis/NIR systems, innovation in optical system design and miniaturization for its friendly use directly in the field. Spectra of intact grapes and grapes skins were recorded at harvest time in two different vintages (2016 and 2017 respectively) using a portable micro NIR spectrophotometer (908-1676 nm). A number of chemometric approaches have been used for spectral interrogation and evaluation of the aforesaid device. Spectral data have been correlated with red grape skin extractable polyphenols (total phenolic, anthocyanins and flavanols) by modified partial least squares regression (MPLS) using a number of spectral pretreatments. Moreover, different statistics strategies have been performed to develop a qualitative analysis of the data (linear discriminant analysis, discriminant partial least square analyses and Pearson's similarity index). After an exhaustive analysis of the obtained results in two different seasons, it can be concluded that the use of the portable micro NIR device for the "in vineyard" screening of extractable polyphenols in red grape skins is hampered by a number of factors. Environmental and physiological conditions should be considered to evaluate and remove factors that hamper a good sorting the berries according to their extractable polyphenol contents.