A routing and scheduling computer system that is adapted to define a plurality of geofenced areas and to monitor vehicle activity within each of those areas (e.g., via telematics sensors mounted on vehicles traveling within the areas). The system may be adapted to use information regarding the monitored vehicle activity to estimate: (1) a first amount of time associated with the delivery of a plurality of parcels to one or more respective locations within a first one of the geofenced areas; and (2) a second amount of time associated with the delivery of a plurality of parcels to one or more respective locations within a second one of the geofenced areas. The system may then route a particular vehicle to make one or more pickups or deliveries within the first or second geographic areas based at least in part on the first and second estimates of time.