Introducing questions of representation in a globalized world, this chapter suggests ways that travel journalism can escape stereotypes and misrepresentation. Travel journalism often produces stereotyped realities, but the plurality of opinions available on sites like TripAdvisor allows for more open discussions about these issues. This chapter takes the example of TripAdvisor to compare forum threads to travel articles dealing with similar topics. These cursory comparisons demonstrate how travel journalism does not have the final word on topics related to a destination, and how conversations can continue through social media. These realizations are important for travel journalists’ understanding of their role as mediators of people, places, and culture. In a way, social media can help challenge stereotypes and clichés, theoretically holding travel journalists accountable for their representations – a sort of Fifth Estate. The chapter suggests the need for further reflection on how travel journalists can use these social media sites as reporting tools to help more accurately or more completely discuss a destination. Moreover, professional travel media and sites like TripAdvisor should be conceiving of innovative ways to collaborate with each other more intelligently.