In modern societies the activity of driving has become almost an essential routine. Vehicles are considered by many as indispensable tools for accomplishing their daily tasks and they are the main form of transportation for millions of people. The average driver spends, voluntarily, considerable amounts of time on the road, using their vehicle to transport himself even for small distances and knowing that its use presents him with some form of comfort and convenience; yet, drivers frequently regard their road experience as tiring and fastidious, but their persistence in using their vehicle at every opportunity serves as proof of a pleasurable experience. So far car manufacturers, traffic authorities and designers of technology have been mainly concerned with aspects of the road that ensure drivers safety, increase power engine, provide more comfort, and maintain better streets, etc; however, the actual feelings of the driver as he travels through the streets has not yet been taken into a great account by the developers of the road environment. For this reason this thesis tries to create awareness on the existence and constant presence of people’s emotions as they drive, which have the mutual power to influence their action on the road and their driving patterns. In order to capture a drivers’ emotional experience this study uses three main methods. One of them is Cultural Probes, consisting of common objects specifically Postcards, Pictures, and Web-logs, to measure unknown factors about the users. The second is the use of Ethnographic studies on the driving activities through the use of observations, the popular talk-aloud-protocol and the shadow method. Finally, the Experience Sampling Method is used, which tries to captures the experience of an individual as it unfolds in its natural context. With the combined used of these three methods some of the main factors of the road’s environment that are commonly able to influence the driver’s emotions in negative or positive ways were discovered, which include the intensity and type of light, the different types and sources of sound, the perceivable landscapes and surrounding architectures and the different kinds of continuously occurring interactions. These are just some of the many factors that can influence emotions on the road, and hopefully this study will open the curiosity for a deeper study of these and other aspects of the emotional driving experience.