This special issue contributes to island studies highlighting a variety of contexts, topics, and theoretical and conceptual depth, with a focus on sustainable development. Island studies is an interdisciplinary research field that covers varied perspectives and contexts, highlighting natural, geographical, social, economic, and many other perspectives and theoretical strands. One special feature of island studies is that there are as many contexts as there are islands, therefore, the study of islands requires both a theoretical and conceptual depth, as well empirical richness. The articles published in this special issue depart from the realization that meeting the varied expectations on island communities, more research is needed. Contributions are based on experiences from Croatia, Finland, and Sweden, highlighting how archipelagos are envisioned in social media and the consequences of from primary production, e.g., fisheries and agriculture being replaced by tourism by highlighting tourism entrepreneurship, drawing lessons from seasonal tourism and multi-seasonal tourism. However, most articles highlight various challenges and opportunities for sustainability by analyzing the changing role of second homeowners, demographic challenges, and obstacles to permanent residence on islands, democracy gaps, and solutions to meet sustainability challenges in studied countries.