Makes sense visually
This is the first Jimmy Buffett video I've seen and visually, it nearly matches what I have in my mind everytime I hear the song. Mr. Twain, the horse, wouldn't have made sense to me if I hadn't been reading Jimmy's novel, "A Salty Piece of Land". The song is about moving on with your life and taking another route when your life isn't making sense. The part of the verse that says, "...Sail upon the ocean, just like Mr. Twain. Never look back, this is my plan..." means, to me, that once you've taken that different route you're determined to take, count on never looking back because what will now be in the past will stay in the past and it makes no sense to go back to that place in time. "Leave my cares behind, take my own sweet time. Ocean's on my mind..." Mr. Buffett is telling us to enjoy ourselves and leave all our cares behind on shore or at home. And that's pretty much what the song is about. In the video, Mr. Buffett's present gets a visit from what his life yet to come if he just takes another road. How appropriate.