This study examines how Nova Gorica and Gorizia, historically divided by a post-WWII border, are tackling the preservation of their built heritage and historic urban landscapes independently and in preparation for the EU Culture Capital 2025. Despite economic challenges and the gradual decline of historic centres, with a stress in the historic Gorizia, both cities aim to protect their unique built identities. Obstacles linked to the administrative asymmetries, lacks of knowledge on preservation, and anxiety to recover dynamism are generating conditions for a potential loss of the heritage values of part of the historic landscape. The research addresses the importance of focussing on proper protection and preservation of the historic landscapes and monuments of the cities by assessing local policies, restoration tendencies, and cultural programmes, stressing the connection between heritage preservation, tourism development, and cultural sustainability. Observations and findings suggest that coordinated strategies and higher standards in preservation are essential for safeguarding cultural heritage and avoiding permanent losses. Such new strategies need to include raising public awareness and enhancing general training and education in heritage, as well as considering culture in its widest concept, the one that connects tangible and intangible without compromises and utilitarian subjectivity.