A multitude of new technologies (ranging from guidance systems to speed-limit exceeding systems and to fatigue detection systems) are emerging, many of which are either explicitly targeted to older drivers or expected to benefit them the most. However, these same older drivers are more likely to find adapting to the use of such technologies challenging. Therefore, understanding older drivers’ perception of such devices will allow experts to take the necessary steps to ensure their smoother acceptance and complete success of their deployment. Using Greek drivers’ attitude data collected within the scope of an extensive recent survey in 23 European countries (the SARTRE-3 data set), a statistical analysis of the perception of usefulness and acceptance of new technologies by older drivers is presented. The results of the developed ordered logit models provide insight into the human-factors’ aspect of the introduction of advanced technologies with respect to these more sensitive segments of the driver population. For example, older respondents are, in general, more supportive of the considered in-vehicle technologies, while female respondents also show a higher willingness to adopt them.