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I have seen several sailboats anchor off Kailua-Kona, the cruise ships and commercial boats also anchor or have moorings there. It's not protected and the boats are in a moderate swell all the time, but it doesn't look too bad generally. You can dinghy into the city dock and walk to all shopping. The only protected anchorage on that side of the big island is at the far northwest corner in the commercial harbor (long way from Kailua).
Honolulu has the Ala Wai marina by Waikiki, transient slips were available when we bought our boat, but I would check current status. Lot's of boats anchor near the airport (Keehi?, don't remember if that's the name), but you are right under the end of the main runway so don't plan on getting any sleep there.
Sounds like quite a trip, fair winds.
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John
SV Laurie Anne
1988 Brewer 40 Pilothouse
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