The 2021 edition of the Italian Highway Code includes for the very first time the vulnerable road user (VRU) category. This innovation reflects the growing awareness of the Italian legislator for the safety of pedestrians, two-wheelers, and persons with disabilities. The coexistence of all road user categories is the specificity of urban mobility. In this context, a significant amount of vehicle-pedestrian collisions occurs at unsignalized crosswalks located between consecutive intersections, i.e. in the so-called “mid-block” section. This study investigates the effects of two different crosswalk designs, (i) the linear sidewalk and (ii) the curb extension, on driver pedestrian (DP) interaction. Two types of driver familiarity were explored: (i) the route and (ii) the situational one.