The first road is more of a spiritual one, though it does involve lots of travelling. I can see why some people might find Mike Scott a bit annoying - the details of his journey aren't as interesting to us as they clearly are to him - but this develops into epic song so stick with it.
The second Mike Scott track to make my little list will also irritate some listeners being a bit too Celtic. I like the humour of it myself, and the swirling instrumentation. A 'bang on the ear' is apparently the Irish equivalent of a peck on the cheek - wouldn't you just know?
Rod McKuen wrote one of the archetypal songs of this kind (all the women in all the places). His own version doesn't seem to be available anywhere. The song was covered by Sinatra (amongst others) but that's not on YouTube either. Fortunately Johnny Cash's is.
Dave Loggins' song is a variation on this theme. He travels, but his woman stays put and repeatedly punctures his romantic dreams. She just wants him to come back home. (I always assumed that this was by Kenny Loggins of Loggins and Messina theme but Dave is apprently his cousin).
The Waterboys -A Long Way to the Light (doesn't seem to be on YouTube but if you've got Spotify (and you should have) click for the link) (Amazon)
The Waterboys - And a Bang on the Ear (Amazon)
Johnny Cash - Love's Been Good To Me (Amazon)
Dave Loggins - Please Come to Boston (Amazon)