The negotiation of expectations in tourism is a complex and dynamic process – one that is central to the imagination of cultural difference. Expectations not only affect the lives and experiences of tourists, but also their hosts, and play an important part in the success or failure of the overall tourism experience. It is for this reason, the authors argue, that special attention should be given to how expectations constitute and sustain tourism. The case studies presented here explore what fuels the desires to visit particular places, to what degree expectations inform the experience of the place, and the frequent disjunctions between tourist expectations and experiences. Careful attention is paid to how the imagination of the visitor inspires the imagination of the host, and vice-versa; how tourists and host communities actively imagine, re-imagine, and shape each other’s lives. This realization, has profound consequences, not solely for academic analysis, but for all those who participate in and work within the tourism industry.