Transport planners face the growing need to understand the behavior of their users, who base their mobility decisions on several factors, including travel time, quality of service, and security. However, transportation is usually designed with an average user in mind, without considering the needs of important groups, such as women. In this context, we analyzed 300K tweets about transportation in Santiago, Chile. We classified users into modes of transportation, and then we estimated the associations between mode of transportation, gender, and the categories of a psycho-linguistic lexicon. Our results include that women express more anger and sadness than expected, and are worried about sexual harassment. Conversely, men focus more on the spatial aspects of transportation, leisure, and work. Thus, our work provides evidence on which aspects of transportation are relevant in the daily experience, enabling the measurement of the travel experience using social media.