This paper focuses on exploring the emotional experience of driving and aims to identify some of the aspects that may influence this experience. The paper presents an exploratory study focusing on the driver’s experience during interaction with the vehicle interface while driving. The study is based on a data triangulation approach including interviews, observation, and think-aloud protocol. Preliminary analysis of the study provided encouraging indicative findings, identifying aspects of design that enhance and/or detract from the driving experience. Previous analysis suggests that context and situation have a dominant impact on the driving experience. Further analysis has shown that challenges with the interface under particular conditions, within high traffic contexts, can bring about positive emotional experiences for drivers. The paper concludes with implications of the findings to future design of driving interfaces and outlines further study directions.