The study aims at comparing the ways in which different cultures perceive the experience of cycling holidays by analysing texts that promote this kind of tourism, i.e., website texts produced in three linguistic and cultural realities: Germany, Italy, and The Netherlands. The underlying assumption is that promotional tourism texts are influenced by the cultural peculiarities of their target groups: in order to produce functionally effective texts, authors must take into account their readers’ attitudes and expectations towards a specific destination or – as in this case – a specific activity. The comparison focuses on the different profiles of potential clients addressed by the texts and on the main topics used as “promotional levers”. Some translations in German and Dutch are then analysed to ascertain whether they reflect the same differences and cultural characteristics found between the original texts. Finally, the benefits of linking Translation Studies and Imagology are briefly discussed.