This thesis investigates the notion of understanding in the seminal texts of Exploratory Practice. Despite its attempts to shift from a traditional view of understanding, Exploratory Practice does not elaborate an alternative concept to ground theoretically this new pedagogical approach. This work attempts to contribute to fill this gap, based on the assumption that there is substantial affinity between Exploratory Practice and the philosophy of Ludwig Wittgenstein, who devoted special attention to the notion under investigation in this thesis. Thus, the objective of this research work is to explore affinities and discrepancies between the Exploratory Practice program and the Wittgensteinian perspective of language, with focus on the concept of understanding. More specifically, it attempts to develop a conceptual reflection on the notion of understanding on the basis of a Wittgensteinian conception of language. The analysis of seminal texts of Exploratory Practice accomplished in this work will demonstrate that the guiding principles of this program are compatible with a Wittgensteinian-oriented characterization of understanding as a concept that, among other factors: (a) is simultaneously invulnerable to essentialism and skepticism; (b) is apprehensible by family resemblance; (c) is taken as an abiding condition and not as a mental occurrence; (d) is determined by regulated and public actions shared by members of the exploratory community; and (e) is considered as an occasion ultimately favorable to denaturalization of well established cultural practices. Furthermore, the analysis points towards discrepancies between exploratory and Wittgensteinian discourses, with specific reference to the issue of autonomy of language in relation to thinking.