One option is to "wing it" - make a solid pine hull using a bandsaw or belt sander. Do this ahead of time, as it's not something you want him to attempt. You present the kid with the hull, and then ask hom what should we do next. You can add masts, sails, strong, life preservers, or whatever you want. Let him paint it and add whatever he likes on the deck. Maybe add an additional "layer" in the aft (IANAS) with ladders, the wheel for steering, portholes, lifeboats, etc. etc. etc. Suggest things to add if he's not sure.
Let the kid decorate it. Buy some miniatures and let him paint them, and glue them on.
And then - try floating the thing in a bathtub. It may not be stable - never tried. May have to add some weights to the bottom to keep it bottom heavy.
The point is, once you make the hull - the rest of the design is left up to the kid. It lets him use his imagination - and he can be as silly as he wants to be, or as serious. He wants a four-poster bed on top, and a hot tub with a TV. Sure.
It's unstructured, and open-ended. He might be done with it soon, or may keep going. Let him decide when it's done.
If he had fun, then perhaps take him to a hobby shop and look at the easy models. See if he wants to do something more "sophisticated."
You will have the memories of the first model, and every model he makes afterwords can only get better. I bet you will have memories of the "first model" for a long time - even if it's the only one he makes.