To encourage greener cities while reducing the impacts of the transportation system—such as impacts on climate change, traffic congestion, and road safety—governments have been investing in sustainable modes of transportation, such as cycling. A safe and comfortable cycling environment is critical to encourage bicycle trips because cyclists are usually subject to greater safety risks. Engineering approaches to road safety management have traditionally addressed road safety by reacting to existing collision records. For bicycle collisions, which are rare events, a proactive approach is more appropriate. This study described the use of bicycle-related macrolevel (i.e., neighborhood or zonal-level) collision prediction models as empirical tools in road safety diagnosis and planning. These models incorporated an actual bicycle exposure indicator (the number of bicycle kilometers traveled). The macrolevel bicycle–vehicle collisions models were applied at the zonal level to a case study of Vancouver, British Columbia, Canada. Collision-prone zones in Vancouver were identified, and the highest-ranked zones were diagnosed to identify bicycle safety issues and to recommend potential safety countermeasures. The findings from this study suggest that the safety issues may be a result of high density and commercial land use type, coupled with a high traffic volume, particularly on arterial routes, and high bicycle volumes on routes with mixed vehicle and bicycle traffic. The case study demonstrated the use of the models to enhance bicycle safety proactively.