The port of Southampton, seated at the confluence of the rivers Itchen and Test in the south of England, ranked as one of the leading ports of England in the fifteenth century. When they are used together they reveal the story of both long distance and inland trade in this fifteenth-century port city, uncovering the organization and discerning the differences that existed in the overland trade in wine from Southampton to the two cathedral cities of Winchester and Salisbury in the fifteenth century. The inland trade of late medieval England has been studied and has taken a back seat to long-distance trade. The grand manors in the surrounding countryside added further to the demand for wine. The inhabitants of Winchester and the tenants of the Bishop, being free from the custom of Southampton, provided another rich market for wine. The wine distribution trade from Southampton to Winchester was concentrated almost entirely in the hands of the great merchants of Winchester.