Abstract: In some embodiments, a computer-based, pickup and delivery system is configured to perform a pickup/delivery route optimization and dispatch optimized route information to client applications. The optimization may include optimizing the routes for servicing multiple delivery and/or pickup stops. The optimization may also include optimizing the route navigation along the routes from one location to another. The optimized navigation may include generating a destination mapping throughout, for example, an apartment complex or a business park, and determining conveniently located parking to be used to park delivery vehicles, conveniently located staircases, conveniently located elevators, access codes to the secured gates and lockboxes, and the like.