Dave Wright brings up a very good point....and that is, "what's to leeward"?
On the leeward side of the islands you can get some decent breeze and the swell is relatively small. That's fun sailing and if something breaks you have many hours before you get out of the wind/wave shadow of the island, so as long as you have a radio or something, you can get rescued.
On the windward side you get a LOT of breeze and bluidy enormous swells, which often break, and that's seriously challenging. However, if something breaks, you'll wind up onshore...somewhere. Hopefully there will be sand and not 100 foot tall lava cliffs, hopefully it won't be on some ginormous surf break but at least there's a chance of fetching up on sand.
However, when you go between the islands, if something goes wrong, it's 2,000 miles to the next land. That's a bluidy long way. Our man is going to be awfully hungry and thirsty...read "dead" before he finds the next hard stuff. ANY 16 footer has a significant chance of a *big* knockdown or worse out there. Bust the mast and you're screwed. Screwed could pretty easily mean dead.
Sail Scamp or a CS 17 around the leeward side of the islands all day long, you bet. Take Scamp or a CS 17 outside Kaneohe Bay and poop around in the ocean swells...well, I wouldn't do it, but it's not completelyh beyond the realm of sanity. Take Scamp or a CS 17 from Honolulu to Maui on anything but a flat calm day? No. Just No.
Need more information.