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Since the earliest of times, islands have captured the artistic imagination—and, often, for the artist who finds his or her muse in being ‘islanded’, the smaller the island the better. Archipelagos offer an ideal setting for artists who take their inspiration from place: on small islands off islands they can experience an intensity of island living they might not otherwise have on a main island: boundedness and connection, isolation and community. This paper examines expressions of islandness by artists who live on islands off islands that are poles apart—‘archipelagos’ of the Canadian North Atlantic and the Great Southern Ocean. It draws upon interviews with those artists and writers to consider the nature of humans’ attachment and attraction to islands, exploring through the lens of phenomenology what Stratford et al. call the “entanglement between and among islands”.

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Phenomenology lends itself to the study of islandness, and because works by poets and painters are often rooted in place they are also highly amenable to phenomenological studies. In such studies, threads of similarity and connection in people’s experiences of living on islands are revealed in ways that are of interest to geographers as well as those in allied and complementary disciplines. This article describes research in Tasmania and Newfoundland by a poet and academic profoundly interested in place. Based in interpretive and qualitative research methodologies, the methods used in the study included participant‐observation and semi‐structured interviews with writers, artists, and musicians whose artistic practices were expressive of islandness and abductive analysis. In addition, poetic interpretations became part of an iterative process that enabled my engagement in phenomena shared with and by participants. Poetry became a way to creatively reimagine academic research and offered opportunities to deepen contextual understanding and insight into people’s understandings of islandness in ways not always possible through academic avenues.

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