Shanen-
If you know a good travel agent (go by recommendations of friends nearby) I would do that for someplace I've never been. Talk to people who've been there (sorry, not me). Check out the airfare specials (check out the websites like trip.com, hotwire, orbitz, Smarterliving.com and bestfares.com. Compare information and make the best decision for your needs. Some people like to know everything is taken care of and they hired a professional to do the job. I can't sit back and feel that a travel agent is as invested in my trip as I am, and I micromanage the booking of my vacations as a result. I select the hotel, the air carrier, the flight, etc. Check out lots of sites online that rate attractions in Maui and get an idea of what kind of vacation you're looking for. More take tours and see everything, or more explore on your own and risk not finding every nook and cranny? More wear yourself out or relax? That kind of thing.
Sorry I can't be more helpful....
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Have a happy day!