Driving is a high-demanding task, related to human capacity, required performance and events occurring in the external environment. In this context, the driver's health status monitoring is expected to support safety system and reduce the number of traffic accidents. Among the drivers' conditions, drowsiness and distraction are thought as crucial risk factors that may result in severe injuries. The paper defines a transdisciplinary roadmap to monitor the driver's health status and to map the perceived user experience, based on three layers: the human conditions to detect, the vital parameters to be monitored, and the adopted technologies. The paper proposes a technological set-up focusing on the driver's drowsiness detection, in the context of smart city framework and innovation 4.0. Indeed, such technologies could be embedded in the future “smart car” and communicate with external services to control the driver's performance and improve the safety inside and outside the car. A preliminary technological set-up has been realized embedded into a Maserati car.