One means to be familiar or be acquainted with, the other is to know like knowing something or having knowledge about something. You know about a road but being familiar with it may imply a more concrete, more profound level of knowledge.
Rey : looks for WayFinder
Do YOU know where the wayfinder is? Do YOU Know where it is? helppppp
Fox be like : Do u know de way Do u know de way Do you know, do know, do you know- (Rey gets ticked off and pulls out her lightsaber) HOLY SH**!!