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Optimization of agricultural practices is key for facing the challenges of modern agri-food systems, which are expected to satisfy a growing demand of food production in a landscape characterized by a reduction in cultivable lands and an increasing awareness of sustainability issues. In this work, an operational methodology for characterization of vegetation biomass and nitrogen content based on close-range hyperspectral remote sensing is introduced. It is based on an unsupervised active learning technique suitable for the calibration of a partial least square regression. The proposed technique relies on an innovative usage of Shannon’s entropy and allows for the set-up of an incremental monitoring framework from scratch aiming at minimizing field sampling activities. Experimental results concerning the estimation of grassland biomass and nitrogen content returned RMSE values of 2.05 t/ha and 4.68 kg/ha, respectively. They are comparable with the literature, mostly relying on supervised frameworks and confirmed the suitability of the proposed methodology with operational environments.