Various embodiments of a system and method for generating a delivery plan for multi-tier delivery schemes are described. Embodiments may include generating a delivery plan for a region including multiple delivery locations. The delivery plan may specify at least one agent delivery route within the region. The delivery route may include at least one shipment acquisition location coinciding with an expected travel route of a vehicle conveying shipments. The agent delivery route may be traversed by an agent that is to deliver a specific group of shipments acquired from the vehicle at the shipment acquisition location. Embodiments may include selecting the specific group of shipments for delivery on the delivery route. The selecting is based on a time constraint for delivering the group of shipments to respective delivery locations along the delivery route, and historical delivery time information for previous deliveries to the delivery locations along the delivery route.