This essay explores the idea of insular peacefulness that is indicated based on the measurable premise of island communities in which killing is absent or statistically low. Insular peacefulness is explored in three sections. The first section presents the notion of a deep-rooted archetype of islands as places of freedom, wealth and peace which can be traced to mythological and historical constructions scattered through time and space. Ancient descriptions are followed by the late medieval and modern quest for lost insular paradises which are also depicted in fictional literary utopian accounts and contemporary libertarian seasteading projections and experiments. The concept of “Peace Island,” following Ko, is also introduced to contextualize the case study sections.Beyond utopian archetypes and realizations, the next section lays out three real insular communities that have been described as “peaceful” or “nonviolent”and that follow our criteria of being essentially killing-free islands. The three featured societies are Tristan da Cunha (British South Atlantic), Ifaluk (Micronesia) and Tahiti (Polynesia). Even if the strategies and structures of these remote and small communities are not necessarily applicable to larger insular populations, they certainly support the idea of the possibilities for realizing nonkilling societies through revised socio-cultural heuristic models.The final section offers another four examples of larger islands that have defined themselves—through collective social imagination and/or intentional constructions—as “islands of peace,” seeking to develop, position, and export their identity in the framework of insular cultures of peace, upon distinct bases within their historical, political, economic and cultural roots. The Åland Islands in Finland (one of the first demilitarized and neutralized territories in the world); the Islands of Hawaii (with a fragile “equilibrium” of heavy militarization and a deep-seated traditional culture of peace and aloha); Jeju Island in Korea (with one of the most active programs for Peace Island development, even if located in a country still technically at war for the past sixty years) and the Canary Island of Lanzarote in Spain (a new international initiative for the diffusion of human rights and a culture of peace). All four examples illustrate through their commonalities the modern attempts for the realization of peaceful and peace-making cultures, programs and experiments from the standpoint of insular societies.