This study provides a critical and interdisciplinary review of the archaeological record of the Aeolian Islands (Italy), from their earliest settlement in the mid-sixth millennium BC (Middle Neolithic) to the establishment of trans-Mediterranean networks at the end of the second millennium BC (Final Bronze Age). We combine archaeological, archaeometric, bioarchaeological and environmental data to explore the interplay between different prehistoric practices and their spatial settings, revisiting old evidence and presenting new data. The resulting picture reveals different levels of interaction and the critical role of these small island communities in establishing and/or facilitating networks at the local and (inter)regional scale. Ceramic networks allow us to trace connections between the islands and their neighbours, underscoring the centrality of the island of Lipari, which is further supported by the spatial analysis of the settlement data, in particular concerning the growing web of intervisibility between contemporary settlements on the Aeolian Islands, Sicily and Calabria. We also highlight significant environmental factors, such as arid phases and volcanic events, and assess their impact in light of the islanders’ responses, underscoring their long-term adaptability to the challenges of insularity. The study is supported by a new and up-to-date database of 50 prehistoric sites, incorporating unpublished results of ongoing archaeological investigations by the authors.