This study explores how familiarity and attachment, along with cognitive and affective image explain destination loyalty across visitors with divergent degrees of frequency of visitation (low vs. high). Serbians (n = 401) who have previously visited Greece comprised the sample population for this study and were surveyed using a self‐administered questionnaire. Findings reveal that overall familiarity shapes cognitive and affective destination image, while each image component uniquely explains destination loyalty (R2 = 0.51). Differences also exist in the magnitude of the relationships tested among the two groups. Implications for theory and practice, along with limitations and research directions, are discussed.