Bromelain is a mixture of cysteine endopeptidase usually extracted from pineapple juice and is used for the treatment of various human diseases and in industrial applications. Bromelain demand is quickly increasing, and its recovery from pineapple residues appears to be a sustainable waste management strategy. Pineapple core is among the most significant waste materials in the production of canned pineapple and is richer in bromelain than other pineapple residues. In this project, we compared the enzymatic properties and composition of bromelain extracts from either pineapple core or pulp to address the recovery of bioactive bromelain from pineapple core, thus contributing to the valorization of this waste material. Although significant differences were detected in the protein content of the two preparations, no differences could be detected for their proteolytic activity and for the effect of pH on their enzymatic activity. Mass spectrometry (MS) approaches identified the same peptidases in the fruit and in the core. This confirmed the possibility of using pineapple core to obtain relevant amounts of bioactive bromelain by applying a relatively simple procedure, thus paving the way to implementing a circular economy in this specific industrial sector.