The advent of Web 2.0 has revolutionized many areas of marketing, among them product design, distribution, and communications. Understanding what the consumer/tourist wants has thus become increasingly important. To that end, a new concept has been proposed, that of expects—expects being short for expectations or expectancies—, to better render the complexity of purchase behaviour. Web 2.0 has also given rise to the phenomenon of social networks. In the wake of these interactive tools, many Destination Management Organisations (DMOs) have designed photo and experience sharing sites. Using three sites as case studies, this article demonstrates the usefulness of the expects concept for analyzing sites, including the identification of their appeal and the evaluation of their theoretical potential in attracting and retaining users.