Island regions and isolated communities represent an understudied area of not only clean energy development but also of innovation. Caribbean states have for some time shown interest in developing a regional sustainable energy policy and in implementing measures which could help to protect its member states from volatile oil markets while promoting reliance on local resources. Here we examine four case studies of renewable energy advancements being made by public utility companies and independent energy companies in the Caribbean. We attempt to locate renewable energy advances in a broader historical framework of energy sector development, indicating a few policy lessons. We find that different degrees of regulatory and legislative sophistication have evolved in different islands. Islands should have specialized policy focus, contrasting the ad-hoc nature of current regional energy policy discussion. We also conduct a cost benefit analysis which shows that these early, innovative alternative energy projects show themselves to be both profitable and significant sources of emissions reduction and job creation. This lends support to the potential benefits of regional energy policy.