The tradewinds put that west side in an offshore wind situation, sometimes a sudden fierce breakthru of a wind shadow situation. There are various micro zones where sailable winds curl around high terrain, like maybe around Kaanapali where I have seen Hobiecats on the beach. I think you need local knowledge, or take a ride on bigger sailboats there with motors.
Beware of the outflow from the saddle between 2 mountainous regions. It can be dead calm from wind shadow until an explosive breakthru later in the day. I have almost been swept out to sea into an even worse wind funnel between the islands, simply from snorkling near Hapuna beach. In seconds on a clear day it went from calm to about 50kts which caused the top 8 inches or so of water to flow like a river offshore which my fins could barely counter. My snorkle top whistled like a siren.
In the vast Kihei bay I saw just one Hobiecat that got its sail shredded in similar conditions, and helped them push ashore. It is an area that appears in the news for kayakers losing their spouses in offshore wind events. It's always the wife that is lost, and I wonder if it was the wind or preplanned. The bodies and wifes kayak are never found.
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