This study travels to four archipelagoes—the Wadden Islands in the Netherlands, the Cyclades in Greece, Shetland in Scotland, and the Aeolian islands in Italy—to examine links between collective pasts and imagined futures as expressed in energy and sustainability projects. It is the result of a four-year PhD research, funded by the European project HERILAND that explored the relationships between heritage and spatial planning in Europe. In this thesis, I discuss the roles of heritage in sustainability action across geographical difference. Heritage is a relevant lens through which to critically and creatively examine histories of cohabitation, confrontation, power, and rights in the relationships between humans and environments. This becomes particularly relevant at this time of environmental and social crises, when the reliance of sustainable development strategies on technocratic, top-down, and large-scale solutions fails to counterbalance continuing global agendas of extraction and growth, and address issues of environmental and social justice in ‘peripheral’ places like the islands studied. Instead, I stress the need to ‘think small’, and ‘look back’ arguing that seeds for meaningful change exist in such places and the relationships between people and environments afforded by their unique historical and geographical realities. To approach this, I construct a kaleidoscopic conceptual framework informed by critical heritage studies, planning theory, cultural geography, environmental humanities, and other scientific areas. Their intersection makes it possible to examine landscapes both as nodes in global networks and as distinct lifeworlds of human communities and non-human actors. More concretely, I engage with the local frictions produced both by climate change and climate mitigation—the fragile consensus around a solar park in the Wadden Sea, conflicts around wind turbine towers in the Aegean, experiments with the tides in Shetland, and volcanic episodes in the