This study examines the role of gastronomy as a lever for cultural entrepreneurship in the remote islands of the South Aegean—Rhodes, Kos, Kalymnos, Astypalaia, and Karpathos. The aim is to highlight gastronomy as a strategic tool for strengthening local economies, enhancing tourism development, and fostering sustainable entrepreneurial initiatives. Using a quantitative research approach, the study records tourists’ preferences for gastronomic travel, existing entrepreneurial activity, and the prospects for developing new business opportunities that capitalize on local gastronomic heritage. The findings indicate a growing interest in gastronomic tourism, particularly on islands such as Kalymnos and Kos, while also underscoring the need for targeted promotion policies, stronger collaborations between local producers and tourism enterprises, and enhanced digital promotion strategies. Overall, the study demonstrates that gastronomy can function as a catalyst for the sustainable development of remote island destinations, reinforcing local identity and improving the competitiveness of tourism-related businesses.