I've been to all the islands and just never recalled much of a sailing profile in the area... and couldn't figure out why, especially considering the history of the Polynesians. Seems to me if one lived on one island, the kick might be to visit other islands. I was just on the Big Island, and I know of at least 3 harbors there, and Maui is about 28 miles away... and there are nice sheltered bays or harbors at either Hana or Lahaina.

I could see high winds and heavy seas being an issue, but again, almost daily I would see Polynesian double hulled canoes with their "inverted" sails taking off from the local canoe club.

I got to wondering if a modern heavy design would fare well... you know a heavy cruising cutter type design... GRIN.