With a view to promoting and cooperating with and between cities that identify and embrace creativity among the factors likely to lead to urban development with sustainability criteria, the UNESCO Creative Cities Network (UCCN) was founded in 2004. Three UNESCO Creative Cities are in the central interior of Portugal. Due to their location, these cities have specific characteristics and have become areas that have seen a systematic decrease in the resident community, progressive ageing of the population, and more difficulty in maintaining and retaining younger people. We propose a comprehensive approach, drawing up a SWOT analysis for each case, a summary of the most relevant economic activity, and how they have incorporated the status of Creative Cities into everyday life and cultural programming. Suggestions for development and/or improvement will be made, bearing in mind how each city’s specificities can achieve competitive and sustainable advantages in and through it. The data will be collected over five years, between 2019 and 2023, and obtained from official and secondary sources. We aim to contribute to a more detailed knowledge of the reality associated with Creative Cities, particularly those inland with challenges and limitations that they want to face and overcome. Contributions to science, management, and operators, public and private are envisaged.