Background: Roundabouts are considered one of the safest infrastructure typologies when referring to motorized traffic. Due to their ability to reduce conflict points between vehicles, they have been largely spread, substituting signalized or unsignalized intersections. While the increase in safety for drivers has been largely tackled and demonstrated by researchers, and some efforts have been spent on the side of cyclists, pedestrian safety has not been extensively analyzed yet. Aim: The present paper aims at analyzing pedestrian safety at roundabouts set in two different locations, Italy and Slovenia. This research will highlight differences and similarities in the behavior of walkers at the same type of infrastructure, taking into account the effects risen by diverse road habits typical of the two countries. Methodology: Starting from video footages recorded at the two locations, behavioral analysis, pointing out pedestrian speed, acceleration and crossing time, and a proactive safety analysis, calculating surrogate safety measures for vulnerable road users, have been run. Descriptive statistics and additional statistical tests are developed to compare the two data samples. Conclusions: From the behavioral point of view, results show for both locations faster pedestrian paces than expected, with the Slovenian case having the highest speed values and lowest crossing times. As regarding the safety point of view, Time-to- Collision, Time Advantage and relative speed between oncoming vehicles and the crossing pedestrians permitted to objectively evaluate conflict severity. The calculated percentages of values overcoming the individuated thresholds for determining dangerous events underlines the need to find solutions from both the infrastructural side and pedestrian awareness about their safe behavior.