Nytefall's post reminded me of something. The distances and sizes of things in game is not necessarily what we are using for RP. If Tamriel was taken to be literally 1 for 1 with the game worlds, then the entire continent would be smaller than the island of Manhattan (Except Daggerfall, because that game is an outlier). For a trip from the Imprerial City to Leyawiin, I'm guessing it would take several weeks by carriage. Don't worry about the time in this case though, we'll just assume the events in your posts took place a bit earlier.