Preserving and highlighting cultural heritage is directly related to sustainable development. The adaptive reuse of cultural heritage buildings and traditional settlements can be a core issue in the implementation of a circular economy strategy, especially in remote areas. In this framework, the current study focuses on Kythera, an isolated Greek island. For the analysis of the study area, research in local archives and communication with the municipality and local stakeholders was conducted, while questionnaires addressed to Kythera’s residents and visitors were developed and processed. Thus, both the special features of the island and the needs of the local community were identified, leading to the proposal of three adaptive reuse schemes at a different scale and within a different management model. The first scheme is focused on the institution of “Eghorios Periousia” and proposes the adaptive reuse of the island’s English Schools as focal points for the promotion of Kythera’s identity. The second scheme focuses on the smaller declared traditional settlements and proposes the adaptive reuse of their housing stock as an affordable permanent residence solution. The third scheme focuses on the abandoned neighborhood of Mavrogiorgiannika in the traditional settlement of Karavas and proposes its adaptive reuse as agritourism accommodation facilities.

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