Understanding activity preferences and their antecedents is essential for creating personalized tourism offers and effective destination marketing, vital components of a sustainable tourism destination. Previous studies have provided insights into tourist behavior and activity choices, but without research on activity preferences and their relationship with perceptions of destinations. The literature still lacks an integrative model exploring the antecedents of activity preferences, including tourist characteristics, destination personality, and destination image, and explaining the nature of the relationships between them. This research proposes and tests a structural model of individual characteristics, destination image, destination personality, and activity preferences. A survey was conducted on a sample of 502 visitors to The Trail of Roman Emperors in Serbia. The results confirmed the influence of personality (extraversion, agreeableness, conscientiousness, and openness) and destination personality (sincerity and ruggedness) on activity preferences. Additionally, the model revealed the significant influence of individual characteristics on perceptions of destination personality and image. Managerial implications were given in light of the importance of this research for destination branding that will support long-term destination sustainability.