This paper presents the R’SENS project, the design for a system leveraging the Internet of Things to connect the dots between the user, her car and her environment through the integration of tools belonging to different domains, such as the connected car, the quantified self and web services. The aim of this study is to test a concept through a prototype to explore the possibility of enhancing the user experience of a connected car through the opportune and ubiquitous display of relevant information not only about the car status and the environment, but also the physical status of the driver. The integration of three different user interfaces (i.e., wearable, smartphone and infotainment system) to be used in different moments played a crucial role in the preliminary evaluation of the perceived usefulness and usability of this proof-of-concept.