A method for optimizing a tour having a first segment with an origination point and a destination point and a second segment with an origination point and a destination point. The method comprises: receiving first load data about a first load and second load data about a second load; evaluating a fit of the first load data on the first segment and a fit of the second load data on the first segment; evaluating a fit of the first load data on the second segment and a fit of the second load data on the second segment; ranking the relative fits of the first load data and the second load data against the first segment on a first segment list; ranking the relative fits of the first load data and the second load data against the second segment on a second segment list; assigning the load having the highest ranking fit from the first segment list to the first segment and removing that load from the second segment list; and assigning the load having the highest ranking fit from the second segment list to the segment.