Visual images, from travel brochures and television commercials to internet advertisements, represent a powerful element of tourist destination marketing. This article seeks to understand how destination marketing represents people and places through visual images while examining the role of tourism discourse in the construction of cultural meanings and identity. Using Jamaica as a case study, the researchers explore the issue of contemporary touristic images. A combination of content and discourse analysis was used to examine images included in printed marketing materials and on the DMO’s website drawing upon postcolonial theory as a critical and contextual perspective that provides an interpretation of the meanings that are conveyed by these representations. The main findings indicate that decades after the end of colonialism in Jamaica, marketers perpetuate the presentation of paradisal destination images using visual representations. It is argued that colonial tropes and practices of “Othering” remain fundamental to the meaning and rationale of seeing Jamaica and the travel experience. However, this study also identified strategies that could be further explored in an effort to counteract colonial discourse, as the use of culture and local folkways opens up avenues for the (re)evaluation and (re)representation of Jamaica and the holiday experience