This chapter is organized as a lexicon, examining three key terms for analyzing the geography of small islands: transcalarity, governance and insularity. Each term is considered a polysemic, multi-layered operator. Transcalarity is presented as a vital methodological tool for navigating different scales of analysis, ranging from the micro to the macro and from the local to the global. Following this perspective, moving across scales is considered a vital intellectual practice for grasping the complex spatial relationships of archipelagic territories. Governance is described as the multi-level network of public and private actors and decision-making processes that shape the everyday geographies of archipelagos, which are all too often shaped by jeopardized administrative geographies. Italian insularity is deconstructed by proposing an analytical framework based on four interconnected parameters: 1. distance (measured in travel time); 2. demography; 3. administrative status; and 4. archipelagic geography. Radar charts are used to visualize this model for a set of cases (Giglio, Lipari, Ustica and Lampedusa), demonstrating how this integrated approach can provide a more nuanced, place-based understanding than traditional, often reductive, centre–periphery models.