The Kaili channel, between Molokai and Oahu
is no big deal. It's the Alenuihaha channel, between the Big Island and Maui, that you have to watch out for.
The easiest sailing route
is to go South out of Honolulu and well South of Lanai. If you are coming from Hilo take the long way, around South Point and stay out to sea South of Kahoolawe, Lanai and Molokai. If you try to go the shorter route
to the North you will be on a lee shore until you clear Hawi. Then you will be in the Alenuihaha channel and could encounter winds that have dismasted a good many boats.
The farther away from the islands you go the more consistent the winds will be as the volcanoes on Maui and the Big Island create a venturi effect that generates some dangerous wind
I don't mean to scare you. Just pointing out the safest, most seamanlike and comfortable route between Oahu and the Big Island. There is no reason you could not stop in at Lahaina or Kaunakakai but it would be trickier sailing.
Malie ke kai