Islandness is a contested concept, not just between disciplines but also cultures, entangled with what islands, island studies, and island identity are understood to be. The purpose of this article is to explore some of these different meanings, without necessarily unifying or reconciling them, with the aim of keeping multiple understandings of islandness in creative tension. We begin by considering islandness as smallness, recognizing that though many entry points into island studies relate to size in some way, what constitutes small is dependent on both context and worldview. Next, we consider islandness as culture, and the concept of island identity, which is expressed in varied forms. Finally, we consider framings of islands as others, and the extent to which contemporary narratives linked to islands are really inherent to islands or not. Ultimately, we conclude that although there is much to be gained from appreciating differing understandings of islandness, these multiple meanings make it critical to reflect on context wherever the term is used, and exercise care in assigning attributes and outcomes to islandness.