Considering the idea that online media and user-generated content (Chatterjee 2001; Prati 2007) have radically changed the content and aspect of odeporic literature (Pifferi 2013) and that travel diaries and commentaries are a product of the education, tendencies and trends linked to specific time periods, the present paper proposes a diachronic linguistic analysis of two corpora consisting of past and present odeporic literature. Corpus A is a collection of 25 travel books and diaries written by British travellers, describing the city of Bergamo, in particular Città Alta, between the early 17th century and the beginning of the 20th century. Corpus B is instead a collection of 120 travel reviews published online on TripAdvisor.com in 2017 and 2018, once again by British tourists, evaluating the same city through the eyes of today’s travellers. A linguistic analysis of the two corpora was carried out, proposing a selection and categorization by frequency of the most popular places visited in previous centuries as compared to today, and the related evaluative elements in the two corpora. The digital and paper material collected was analysed with the intention of revealing how a traveller’s perception and evaluation of a specific location and of the voyage itself has changed over the centuries and, ultimately, how the prosumer role of today’s traveller (Milano 2011; Vàsquez 2012, 2014) has evolved thanks to computer-mediated genres and social media (Zeng & Gerritsen 2014).