On the one hand, you'd definitely want a look at the landing. On the other hand, I'm not sure I'd want to be anywhere near the possible impact spot in case of failure.
They used a drone launched from a ship to the film The First falcon 9 landing almost a decade ago so I don't see why that would be out of the realm of possibility.
They're called drone-ships, but they're more drone-barges. You absolutely couldn't take them all the way out into the Indian Ocean in anthing but amazing weather, and they were delivered to their current home on top of another ship.
That's not to say you couldn't have some kind of unmanned observer nearby, but it'll have to be something else. Any yacht with a camera and a good drone would do the trick, you don't need to spend (and risk) millions on custom ships for that.