The present study embarks from a targeted literature review to operationalize classic models of cultural communication in the territory of official Greek tourism websites. The paper explores how cultural awareness is manifested in these spaces through their structure, content and design features vis-à-vis the needs and preferences of their users. Key trends are identified and their significance is examined. Through an exploratory qualitative research, the paper identifies the factors that affect user interfaces and argues that web possibilities are not adequately exploited to promote the Greek tourism product. Websites often do not sufficiently embed emerging technologies of the digital era to address increasingly sophisticated and technology-oriented publics. With this as the backdrop, a novel conceptualization of website evaluation is offered which can be tested empirically and evolved to support functions of cultural adjustment. A concrete structure exemplifies the model and helps illustrate the cultural awareness and sensitivity parameters involved in browsing websites that support the tourism industry. The paper concludes with diagnostic findings and improvement recommendations for destination and professional web spaces to be strategically adaptive to the increasing needs of their diverse audiences.