This is a qualitative study whose objective is to analyze, from a semantic, semiotic, and cultural pragmatic perspective, the self-representative aspects of the Chiquitano identity in the dissemination of its natural and cultural heritage in digital culture. The participants of the study were five hundred teachers, artisans, and cultural facilitators who participated in dialogic interviews and whose answers were corroborated through specialized documentary review. The general result is an analysis of the Chiquitano identity self-representation mediated by digital culture, from the theory of media and cultural studies. The specific results are (a) semantic–semiotic analysis of didactic–cultural praxis, ecopedagogy, and identity self-representation of teachers and cultural facilitators, (b) exploration of diverse interpretations of a singular identity placed in a plural and global context mediated by information and communication technologies (ICT), represented by a model of reconceptualization of interculturality in a virtual context. It is concluded that communicational technological intermediation makes viable spaces for teachers and cultural promoters to disseminate, transfer their heritage, and reflect on their didactic–cultural praxis, from the identification processes experienced generation after generation, thus favoring the transfer of knowledge and wisdom in a close dialogue between the multimodal and tradition. It is concluded that through the reflexive use of communication technologies in the Chiquitano educational and cultural contexts, the identity and dissemination of the patrimonial richness of the Chiquitano ecoregion of Bolivia is enhanced, generating a close dialogue between the singular identities and the plurality of digital culture.