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I'm a little concerned whenever I see "Multi-Island" anything. We'd really like visitors to have a good experience. You pretty much need one week per island, and every transit between islands will consume 4 - 5 hours of your vacation, door to door. In addition, Day One in Hawaii is largely trying to adjust to the time change.
Re: Multi island travel. 6 years ago. Well, easy enough I think. First you will want to book your main airfare from the mainland to your first island, and then back to mainland from your second island. I would go to Big Island first, then Kauai. Compare which is better from your area/cost. Then you book one interisland flight on Hawaiian airlines.
Do it as a multi city. First island then second then 3rd and so on. fly home from your last island. example: Wisconsin to Oahu to island of Hawaii to Maui to Kauai to Wisconsin. You can search flights through Google, Kayak, Expedia etc. I usually start there to see what's available,then usually go to the airline web-site to book.
Don't know when you're traveling or what your budget is, but Costco has one-week Napili Kai ocean-view studio packages for some weeks (May 7-14, for example) for $2,995. If you subtract the price of the car, the cash value of the included gift card, and taxes, that's a base rate of around $300 a night, which is a great deal for those rooms (I have two of those packages booked now).
Here's the Costco travel info # 1-877-849-2730. You can talk to someone here even if you are not a member....simply tell them you are considering becoming a member. I haven't used them, but have called them. (I am a member).
This all depends on how comfortable you are with making your own arrangements. If you are not familiar with Hawaii or booking travel on-line -- I highly recommend using a travel agent. Yes, "Pleasant" is a reliable company with lots of options. You can go on their website and play around - then go see an agent.
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