This article analyses how tourist guidebooks can be manipulated by editors and translators in order to meet their target readers' expectations and appeal to culture-bound prejudices and stereotypes. As cultural mindsets and interpretative filters differ between two countries, the comparison between Italian and English-language guidebooks about Sicily provides a twofold perspective both inside and outside. Through an analysis of the different strategies adopted in the English and Italian editions of the Lonely Planet Sicily, this study aims to stress the mediating role played by translators and to show how the idea people often have of Sicily is based on a construction and is only partially based on the real conditions of the island.