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.

Cultural routes are a well-established development tool to highlight and promote a region’s cultural and environmental reserve, as well as having a positive impact on a region’s socio-economic development. Underdeveloped or rural areas, which have limited financial and technological resources available, often envision cultural routes as a useful development tool to cater to their needs. However, unless these cultural routes are designed and implemented based on the principles of a circular economy or while respecting the region’s cultural identity and heritage, their impact will not be significant. The region of Aitoloakarnania is the poorest prefecture of Greece. The prefecture served as a case study to demonstrate that the utilization of its cultural and architectural heritage can be based on the identification, documentation, and the reveal of paths of cultural tourism along the region’s main natural features, namely its rivers, lakes, lagoons, and coastline. Τhe density and the representative distribution of the monuments in the area, in combination with the unique natural environment of the prefecture, led to the configuration of a mild design of cultural routes, promoting the revealing of both the cultural and the natural landmarks of Aitoloakarnania. In this framework, certain cultural paths were defined. The first one, along the Acheloos River, includes sites of natural heritage, ancient and medieval monuments (castles, fortifications, monasteries, churches, burial sites, archaeological sites, etc.). The other cultural path regards sites along the Evinos River and Trichonida Lake, which includes similar monuments and traditional settlements. A similar cultural path regards cultural sites and points of interest along the coastal parts of the prefecture, and in particular, a path initiating from the historic city of Nafpaktos and following the route to the west, it reaches the Venetian castle of Plagia, opposite of Lefkada. These cultural paths fuse along their routes sites of natural heritage, sites of archaeological and cultural interest, and sites of historic importance to the region. This amalgamation of different types of cultural sites, integrated into a single cultural entity, provide the means for the local and regional development in a sustainable approach while ensuring and disseminating the region’s brand and history.

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A cultural landscape is a complex and integrating concept with both material–physical and immaterial substance. Nevertheless, even today, the strategies for the protection and promotion of cultural landscapes are concentrated only at their material cultural elements, separated from their immaterial existence, or even from the natural environment in which they are placed. This study investigates the correlation of the tangible historical and natural heritage of a cultural landscape with its intangible content, as a spatial planning tool for its sustainable development. The proposed methodology was applied in the region of the Mani Peninsula, located in the southern Peloponnese, in Greece. During the documentation stage, literature research and fieldwork provided descriptive information, which was classified through standardization processes. GIS management and analysis procedures were used among the different layers of data of the current preservation state and the existing development frameworks for the study area. New thematic cultural routes are proposed to connect tangible cultural heritage and environmental values of the region under study, with the landscape’s geomorphological characteristics and intangible content. Protected areas are also proposed for the protection of monuments and sites of historical or natural importance. The results of this study demonstrate that, through integrated strategic planning for the development of cultural activities and networks, which incorporates the principles of spatial and urban planning, not only is the protection of the natural and cultural wealth of the region achieved, but also a balanced economic development and social cohesion, which ultimately leads to sustainable development.