Route planning methods for use by a package delivery service provider are disclosed that satisfy a stochastic daily demand while taking advantage of drivers' route familiarity over time. A model for estimating the value of driver familiarity is disclosed along with both an empirical and a mathematical model for estimating the value of route consistency, along with a Core Area Route Design which involves the concepts of combinatorial optimization, meta-heuristic algorithms, tabu search heuristics, network formulation modeling, and multi-stage graph modeling. In one embodiment, a service territory is divided into unassigned cells associated with a grid segment involving prior driver delivery stops, and a driver from a pool of unassigned drivers is assigned to a route based on examining each driver's grid segment visiting frequency limit with respect to a minimum limit so as to optimize driver selection based on of each driver's familiarity with the route.