Background: Smart mobility can contribute to the design of “Smart cities” to answer users’ requests in terms of transport network efficiency, environmental and social sustainability. Focusing on urban smart mobility issues, the most important aspects are the presence of a connected transportation system, the availability of its information in the arrangement of digital data and the possibility to rapidly communicate it in an effective way to the citizens, urban transportation stakeholders andlocal authorities. Therefore, the challenges for the new era of mobility behavior would range from the effort of big data management and the need to shape the innovation of traveler demand to the changes in requirements for road design. Nevertheless, road safety issues and network working operations must consider all the automated vehicles (AV) as part of an intelligent transportation system. There are types of active safety systems that can influence people’s lifestyles. Aims: This chapter highlights the working mechanism, advantages and disadvantages of ICT technology applied to transportation in the field of safety improvement, environmental sustainability, road redesign and traveler behavioral change. These topics become significant for the study of the key elements associated to the issues with automated vehicles, when “Smart cities” will have new urban settings or mixed traffic. Discussion: This paper leads to redefining the mobility paradigm. Moreover, thanks to the innovation by traffic flow facilities and road equipment, it has been possible to conduct some case studies describing driver behavior towards land-use environment, unfamiliar routes and sharing mobility. Conclusion: The current technology applied to the transportation system already represents the outlook of a new kind of mobility. Many features deal with technical details and others face ethic or legal restrictions. A review of the entire transportation network program should be considered by 2020, worldwide, to make the necessary effort to reach a realistic smart mobility.