Located at the southern end of the Americas, in the remote and protected archipelagoes of the Cape Horn Biosphere Reserve in Chile, the Omora Ethnobotanical Park is an outdoor “natural laboratory” dedicated to biocultural research, education, and conservation. Every year since 2000, university students have been offered field environmental philosophy (FEP) courses and activities that rely heavily on drawing as an observation and discovery tool. Metaphorically, the course’s “biocultural lenses” not only amplify the appreciation of living beings (including mosses and other small organisms from the perspective of multiple forms of knowledge) but also offer “philosophical lenses” to broaden the understanding of biological and cultural diversity, and to orient ethical forms of co-inhabitation within it. This biocultural understanding has awakened a keen awareness of the fragility of human life (in its cultural diversity) and the entirety of living beings (in its vast biological diversity), with specific life-habits and shared habitats. My short essay begins with a brief personal anecdote linked to a series of watercolor, photographic, and sculptural works to develop a first possible interpretation of the chapter’s title, “‘Fragility of Encounters’ in Subantarctic Biocultural Diversity.” These artworks are open to multiple readings that evoke the notions of encounters and fragility. Based on the analysis of the artwork, I propose that art should assume an ethical role in generating works that pose questions about our relationship with cultural and biological diversity, especially at the current planetary crisis. It is urgent to look toward a state of peace between nations and people to address the problems of poverty, equity, respect, and human migration, as well as the need to care for the fragile balance of the natural ecosystems of which we are a part. In short, art can help us cultivate integral ways of life based on socially and environmentally just forms of biocultural co-inhabitation.