Resumo: The study of destination image through assessment of customers' expectations with an industry perspective is perceived as a challenge, taking into account that travel decisions depends on information that may differ from the true characteristics of the holiday destination and the reality spread by the media and advertising. The present article is the resultof a comprehensive research conducted in Old Havana with the objective of comparing customers' expectations as a reaction to the supply side built image through advertising and the real post visitation image at this Cuba holiday destination. The results obtained provide the basis for strategic decisions to be made for the conformation of the tourist trip.