Definitely start on Oahu. Especially since you’ll spend an entire day traveling. It would be a shame to land on Oahu and have to board *another* flight. Also look into the open jaw. I’m flying into HNL, but out of KOA when I head out this summer. To save on flights and time just start on Oahu and work you way east – HNL, OGG, KOA – this way you don’t have to spend extra time connecting between islands. Each flight should only be about 35minutes.
I thought about the Wailea, but couldn’t get over the price. I’m a first class traveler on a coach class budget
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