I am certain HOC can give you some really nice places to eat, where the locals go! He did me up on our Oahu trip last month
Also heartily recommended for food on Maui (but not near Lahaina or Kaanapali) are:
Mama's Fish House in Paia. Amazing food, fresh fish, very expensive.
Paia Fish Market in Paia. Fresh fish, you sit on long wooden benches at long wooden tables with the other locals, but you get really fresh fish for a much lower price than at Mama's.
Eskimo Candy in Kihei. Great fresh fish to go, and plate lunches with fresh fish. Take them away to the nearby beach or elsewhere, otherwise you'll be sitting on a crowded wooden table outside the shop with many others, next to the trash cans and swatting flies. Take it away from there so you can appreciate the quality.
The spectacular Sunday brunch at the Maui Prince, very expensive, is the best on the island and has live Hawaiian music, to boot. They try (unsuccessfully) to enforce a dress code for men, who are supposed to wear a shirt with a collar. Half the men there wear T-shirts, and many of the men wear shorts. Brunch was great, and bring a bag with your towel and swim wear, as the beach in front of the resort, with chaise lounges, is a great place to catch a nap and maybe take a swim after brunch.
Cheeseburger in Paradise, in Lahaina, is fairly reasonably priced, and a good burger. On the water, but you probably won't get a seat at the window on the water. Upstairs at night they have live music.
Aloha Mix Plate, in Lahaina across from the cannery mall, does a decent plate lunch or dinner for not too much money. In the evening, you will hear the music from the Old Lahaina Luau, which is next door, and if you go at sunset, you are sitting in the open air, on the water, watching the sunset with the music from next door as entertainment.
Sansei has great, fresh sushi and late at night (I think after 11) they serve much of it at half price. Located in Kaanapali and in Kihei.
Wei Wei in Wailuku is pretty much a local "greasy spoon," but they are famous for their Maui Dry Mein, for which Maui is famous. While you are in Wailuku, swing by the Homemaid Bakery, which makes wonderful, fresh mochi or crispy manju every hour, filled with the traditional red beans or black beans, but also coconut, pineapple, peanut butter, apples, or a bevvy of other local fillings. Their banana bread is also good.
Long's Drugs (in the cannery mall and at several other locations all over the island) sells a lot of Homemaid Bakery items, but they are fresher at the bakery, and Long's usually runs out of all the good stuff within minutes of opening.
BTW, on the subject of banana bread: On the Keanae penninsula, along the road to Hana, there is a shack right next to the beach that makes (in my opinion) the best banana bread on the island. But they usually sell out around noon or 1 pm, so get there earlier than that. I was told that there is a yellow house, a bit closer to Kahului (about 7 miles into the road) that has been converted to a shop, and its banana bread is also wonderful. I did not get a chance to try it this trip.
For the room, you can stop by the Farmer's markets (there's a big one in Kahului on Saturdays, a smaller one between Lahaina and Kaanapali on Sundays, and one in Paia on Mondays -- most of the same merchants go to all of them), and pick up some wonderful local jams and jellies (mango, coconut, pineapple, lilikoi, guava, mixes, and many more, as well as butters made with these fruits). Also at the farmers markets are nice smelling soaps that utilize island fragrances, and local fruits and vegetables. And, of course, crafts and clothing that are ubiquitous on Maui, but cheaper at the farmers markets.
While on Maui, try some Shave Ice. If you find a place that has mochi balls and puts sweetened condensed milk on the top on request, you've found a good one. My preference is for Waiola Store on Oahu, but it's not as famous as some of the other places (hence, no line).
Longhi's is hyped, but I ate there twice and found it incredibly, indescribably bad both times. Fish was really old, sauces were bad, and nothing was cooked right.
David Paul's restaurant in Lahaina was also mediocre and overpriced.
And, for gosh sake, don't eat at the same places you eat on the mainland. You can get Ruth's Chris, Bubba Gump's, Subway or Hard Rock Cafe food anytime you want without going to Maui -- the product is standardized, so get it back home.
In the parking lot of the Honokowai Deli is a taco truck that's been getting a lot of buzz lately. Smelled good, but we didn't have time to try it while we were there this time.
There's a small, local diner in Wailuku called Tasty Crust that is well known by locals for its pancakes and breakfasts. They will serve pancakes with peanut butter on them for which some folks will kill.
In the Maui Mall is Guri Guri Sherbet, which has been there since I was a little boy. People would travel from Honolulu to Kahului just for a cup of the sherbet. I never found it particularly appealing, but it has grown on me in my later years. More like an asian ice cream, it's not as sweet as traditional American Sherbets.
Also, while on Maui, get some apple bananas from the market. They are unlike any banana you've ever tried. And if you have not tried pineapple in Hawaii, you are in for a treat. Expect to overeat it, and go home with a mouth full of acid sores.
Pacific'O (in Lahaina) and its sister restaurant, I'o (at the Maalaea Harbor) are also very good and very expensive, but I personally would drive the extra 25 minutes to get to Mama's if I were craving a good, fresh, expensive fish dinner.
Edit: I meant to add Haliimaile General Store (I think it's in Kula). I've never eaten there, but many of the Maui locals say it's really good.
