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Land is divided into fiefs. Fiefs are headed by lords and knights. Only those who are part of fiefs are able to farm limited renewal resources on those fiefs, and they are called villeins. Burgesses are subjects of the Duchy of Wessex, but they are free men. They are not part of a fief, they are part of a boroughs, a town. This is why they are called burgesses and not enfeoffed villeins. But buildings in towns are limited, and the burgesses sacrifices his ability to legally farm from his lord's fief.
Let's say that the Duchy controls 2 territories on the map, that would be 2 fiefs and each fief would have 1 city; so technically speaking there would be 2 cities in the kingdoms. Are the villeins of 1st fief, prohibited from entering, adventuring and farming the 2nd fief? I think free movement between the fief's would apply to the members of the guild.