This paper explores the problematic cross-cultural encounters in Monica Ali’s work Alentejo Blue (2006) set in Mamarrosa, a fictional place in the Portuguese region of the Alentejo. This collection is a composite of nine stories alternately focalised by different characters, posed in an interstitial position between the polyphonic novel and short story cycle. The narrative’s reluctance to fit in genre taxonomies mirrors the heterogeneous nature of the characters’ perspectives, ranging from British expatriates and tourists in Portugal to the locals’ views of these visitors. Such a conflation at a complex cultural crossroads favours no inspiring encounters, but rather fuels feelings of frustration, a profound sense of displacement and a tantalising incapability of solving conflicts. The paper also examines the second story in the collection, which entails the experience of British writer Harry Stanton in the Alentejo as paradigmatic of a subjective projection of the preconceptions and prejudices which most often intervene in a tourist’s construction of place, and which eventually pertain to culturally erected barriers between the self and the Other.