PurposeThe study aims to provide a detailed definition of Destination Cultural Reputation while also exploring its impact on tourist satisfaction through an investigation of the dynamics between these two elements. Additionally, the potential moderating role of on-site engagement in sustainable activities has been investigated, examining whether satisfaction prompts tourists to exhibit behaviors such as the intention to return and recommend the cultural destination.Design/methodology/approachTo achieve these objectives, a survey and a structural equation model, based on a sample of 647 visitors to an important UNESCO World Heritage site (i.e. Urbino), have been adopted.FindingsFindings confirm tourists’ recognition of the destination’s cultural reputation, supporting its relationship with visitor satisfaction. Additionally, tourist satisfaction is positively associated with destination loyalty. However, on-site sustainable activities negatively moderate the relationship between destination reputation and tourist satisfaction. This suggests that a favorable cultural reputation should align with quality sustainable activities in the destination to prevent tourist dissatisfaction.Practical implicationsThe paper offers valuable practical insights for destination managers and policymakers aiming to enhance appeal and sustainability.Originality/valueThe study contributes to enhancing the understanding of the complex relationship between reputation, satisfaction, and loyalty in cultural destinations. In addiction it measures the reputation of tourist destination through the specific cultural dimension.