In this paper, we present results from a collaborative research between academic institutions and industry partners in the UK, which aimed to understand the experience of rail passengers and to identify how the design of technology can improve this experience. Travelling by train can often provide passengers with negative experiences. New technologies give the opportunity to design new interactions that support the creation of positive experiences, but the design should be based on solid understanding of user and their needs. We conducted in-depth, face-to-face semi-structured interviews and used additional questionnaires given to passengers on board of trains to collect the data presented on this paper. A customer journey map was produced to illustrate the passengers’ experiences at diverse touchpoints with the rail system. The positive and negative aspects of each touchpoint are plotted over the course of a ‘typical’ journey, followed by the explanations for these ratings. Results indicate how the design of technological innovations can enhance the passenger experience, especially at the problematic touchpoints, e.g. when collecting tickets, navigating to the platform, boarding the train and finding a seat. We finalise this paper pointing towards requirements for future technological innovations to improve the passenger experience.