Diaspora tourism has emerged as a growing field of academic and policy interest, examining how members of transnational communities reconnect with their ancestral homelands through travel. This study investigates the tourism behavior and decision-making patterns of Greek expatriates, focusing on their perceptions of the Peloponnese—a region of strong historical and emotional significance for the Greek diaspora. The research adopts a holistic analytical framework, combining demand-side perspectives—such as needs, motivations, and behavioral profiles—with supply-side considerations, including the capacity of destinations to develop targeted tourism offerings. Special emphasis is placed on the role of digital tools and contemporary tourism experiences in attracting diaspora visitors while also addressing deeper emotional and cultural dimensions of identity and belonging. Findings show that diaspora tourism is not a homogeneous market segment. Greek expatriates exhibit diverse motivations and travel behaviors shaped by personal and family networks, digital information sources, and patterns of repeat visitation. As such, tailored strategies are essential for effectively engaging these groups. The study contributes to diaspora tourism literature by offering theoretical insights and practical recommendations. It calls for culturally sensitive, data-driven approaches by destination management organizations and policymakers to foster sustainable ties between diaspora communities and their ancestral destinations.