@daringclarky
Doing the fleet might be a tall order, but if you use the cheesy strategy with islands maybe. A single galleon is pretty easy, get some initial shots in, ram into them, stick to them like glue and just bail water into it. Pretty boring, but not a big deal. Technically if you get your speed right and naval positioning, you should even be able to win a shoot out by avoiding broadside enough.
Kraken might actually be the more challenging monster to encounter on a galleon solo. Between the distance of bailing and dealing consistent damage, the grasp even if it is not on top of the hatch might be to much.
It has been a long time ago since I did galleon solo and usually was just already starting with the Athena voyages while waiting for the rest to come on and banging out a couple of the maps. Don't get me wrong, I don't think it is a smart choice.. but it is doable.