Retreating from coastal areas in response to changing environmental conditions has long been a part of Pacific Island communities’ traditional adaptive strategies, culture and practices. One can point to a number of cases of significant out-migration, as well as environmentally-induced partial and staggered community relocations, which surpass the normal migratory processes. Furthermore, many traditional risk management and response strategies have been lost in the post-colonial era, due in part to the pre-eminence of “modern” strategies. This loss also applies to strategies of risk-sharing with traditional trading and kinship partners, who are now found across artificial international borders. It leaves exposed communities and specific vulnerable groups with fewer capacities to respond to extreme weather events and the (potentially gradual but permanent) loss of habitable land (as in the case of low-lying atolls and volcanic eruptions). The result may be the loss of shared social and cultural identities, spaces and meanings; the creation of a bifurcated, altered or hybrid identities. Those who migrate are often in tension with those who return to or remain anchored in the physical source of a shared heritage. These concerns are of particular importance for community members attached customarily owned land. The adverse effects of climate change are likely to increasingly incite islanders to migrate to cope with threats to their livelihoods. This paper explores the extent to which customary land issues are key to the sustainability of population movements in the Pacific region. This is done through a multi-layered analysis of scholarly debates around planned relocation and land rights, exploring divergent cases of environmentally-induced community relocations in Fiji and Papua New Guinea. The paramount contrasting role of the colonial authorities and post-colonial State are highlighted, in relation to the “success” of reallocations and their failed attempts to alienate land from customary owners. Two primary, and conflicting, outcomes of relocation strategies are revealed: one based on the primacy of community cohesion, social development, and the preservation of heritage. The other plays to a neoliberal narrative of economic growth and development, based on individual rights and logistical aspects of the relocation process. We argue for a middle-of-the-road strategy to enable communities to choose an intermediate position. A deep exploration of both ancestral and recent community relocations and customary land tenure is necessary to ensure relocations are sustainable and maintains the link between Islanders and their land, which has been the crux of their identity for millennia.