Hyperstalking (A Car, No Less)
I am so relieved to find that there is another car enthusiast who is obsessed with "stalking" his car. I hadn't thought of that, before, but I guess that's what this is. Here's a video from the How to Hyperstalk a New Car From Factory to Your Door
This appears about as close to a roll on roll off vessel as I will ever get.
My best current guess is that Gentle Leader is headed southeast to the passage between Cuba and Haiti, en route to Kingston, Jamaica, and then the Panama Canal.