This sort of thing is possible. You will want to learn about using the Path shelf feature. http://onlinehelp.tableau.com/current/pro/desktop/en-us/help.htm#maps_howto_origin_destination.html
I would also suggest reviewing this thread - Mapping route's with Origin and Destination in one row . This sort of mapping of paths is one of my more favorite features of Tableau. Good luck and enjoy.
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