WRONG!! =0= Ahh I was so angry for the autosaveTo complete this trophy you will first need to Craft 3 Land Convoys. For this you will need Lance the Woodworker recruited, Oak Bark and Oak Lumber. Once you have three convoys, you must then find at least one General Store in each territory. Now I strongly recommend waiting until you have cleared out the Forts in these areas, so the convoys will be safer. Once you have achieved all of that simply toss at least one item in each Convoy and send one to a store in each location for an easy trophy.
It actually u only need 1 Convoy
then send at least 1 item to 3 different cities in 1 Convoy
not each location in each convoy