The main objective of this study was to assess the effectiveness of several countermeasures at bicycle crossroads on drivers’ behavior during the driver–cyclist interaction (a cyclist that crosses the road) by the use of a driving simulator. Three treatments of the cyclist crossroads were investigated: baseline condition (no treatment), raised island, and the colored paved markings. Forty-two participants drove a suburban scenario with several bicycle crossroads having difference configurations and presence/absence of cyclist. Overall, 252 speed profiles were plotted from 150 m before each crossroad of which 23 showed non-yield events: 12 for the baseline condition, 6 for the colored paved markings, and 5 for the raised island. The method of the survival analysis was applied to model the driver speed reduction time (the elapsed time to pass from the initial speed to the minimum speed during the yielding maneuver) with the use of the Weibull distribution. The model identified the average deceleration, the drivers’ age, and the countermeasure condition as significant explanatory variables. The survival curves highlighted that for the colored paved markings the driver adopted longer values of the speed reduction times and then a less aggressive driver’s braking behavior. Moreover, the outcomes of the questionnaire confirmed that the colored paved markings were considered to be the most effective in terms of driving aid.