Go look for island unloading scenes on youtube for some interesting cargo landings. They unload cars from boats that don't look a whole lot better than the Hawaiian. It can be done. Not that it's a great (or even sane) idea.
I still think it will start to tear itself apart when it hits waves, but maybe I'm wrong and it will live to actually encounter big waves and storm conditions. Those side doors look like they have two storm modes:
Closed up tight, with no way to get up on the roof and do sailorly things with the rig, or open, with a stairwell up and a giant hole in the side of the boat.
I'm in this camp, well maybe sorta.
I further think his bigger problem will be acutally hitting Hawaii!
As he and merry band of misfits drift downwind in the trades, rig blown down weeks ago, batteries long since dead rendering the gps useless, He'll have to rely on his trusty celestial skills to figure out where the hell they are. Then if they get any kind of fix on where they are, trying to figure out where Hawaii is, and how to drift there.
That's gonna be the challenge!
Nah, just follow the planes.