I'm thinking of Randy Dandy-O which I know from Tom Lewis, but I did see in similar form here: Randy Dandy Oh. "Soon we'll be driving her off down the hill," said of a ship afloat.
I feel like I heard an explanation of this phrase somewhere along the line, but I can't place what it means. Sailing a certain stretch is like going downhill because the winds are favorable, or something? Literally downhill because of a bulge in the geoid? It's just one more maritime reference that's familiar to my ear without my properly understanding it, and I keep hoping to catch up with those in the long run.