In the context of hyper-connected cars and a growing heterogeneous digital ecosystem, we wish to make the most of the data available from the various sensors, devices and services that compose the ecosystem, in order to propose a proof of concept in-vehicle system that enhances the driving experience. We focus on improving the driving experience along three main directions, namely: (1) driving and trip planning, (2) health and well-being and (3) social and online activities. We approached the in-vehicle space as a smart interface to the intelligent driving environment. The digital data-producers in the ecosystem of the connected car are sources of raw data of various categories, such as data from the outside world, gathered from sensors or online services, data from the car itself and data from the driver gathered with various mobile and wearable devices, by means of observing his state and by means of his social media and online activity. Data is later processed into three information categories—driving, wellness, and social—and used to provide multi-modal interaction, namely visual, audio and gesture. The system is implemented to act in response to the trafficked information on different levels of autonomy, either in a reactive manner, by simple monitoring, or in a proactive manner. The system is designed to provide an in-vehicle system that assists the driver with planning the travel (Drive panel), by providing a comfortable environment for the driver while monitoring him (Wellness panel), and by adaptively managing interactions with their phone and the digital environment (Social panel). Heuristic evaluation of the system is performed, with respect to guidelines formulated for automated vehicles, and a SWOT analysis of the system is also presented in the paper.