Citizen participation, in the active management and enhancement of cultural heritage, has shown in recent decades that cultural heritage is a dynamic generator of the development of good management policies for abandoned or depopulating territories. An interdisciplinary contribution is proposed, between urban planning and architectural restoration, which aims to investigate the critical issues̀ highlighted by the traditional approach to “inland areas,” as defined by the National Strategy for Inner Areas (SNAI). The case study of the “Inner Areas of the Madonie in Sicily,” can represent an excellent place of investigation in which to understand what are the possible interweavings between different disciplinary approaches and understanding of the potential of the new dynamics of collective participation of local communities in planning policies and conservation of tangible and intangible values. We ask ourselves two questions: what is the qualitative and perceptual dimension of the “inner areas” of the Madonie Mountains, with respect to the heritage that still describes their cultural landscapes? Is there an awareness of this cultural heritage that can become a quality criterion for the development of a design and enhancement of the cultural landscapes of the Madonie? An overview will be made of local development strategies, not codified in official policies, which are a driver of development that is still not integrated into the design and possible financing for land management. The framework of active policies in the Madonie territorial sphere that are based on the enhancement of cultural heritage will also be explored, analyzing their strengths and criticalities. Particular attention will be paid to the potential cultural itineraries not yet codified, which intercept the system of values recognized in the widespread heritages that connect the landscapes and histories of the territory. The great potential of monumental cultural itineraries, such as those of the legacy of the Norman building tradition, still very present in this territory, has been partially perceived by communities and partially used as a development factor. Only some parts of these territories have put in place today enhancement policies that focus on cultural heritage systems spread throughout the territory, capable of narrating a landscape that has been transformed over the centuries, but in which elements such as generative road axes, perspective connections and architectural structures characterized by recognizable building elements as the legacy of a common culture are still strongly present and recognizable. Starting with restoration projects in which collective enjoyment and openness to new policies of sustainable tourism have become new avenues of growth and awareness, new systems of reading these existing heritages and possible strategies of valorization and management that go beyond the local scale will be proposed.