We had a hard time leaving the beach, so we only ate dinner out. We bought groceries at Foodland, the closest grocery store to our condo at Hale Hui Kai. If you've been to Hawaii before, you know that grocery prices are outrageous. Foodland seems to have the best prices (there was a Safeway and a Star Market further north up Kihei Road), but make sure you get a temporary discount card from the cashier to get the sale prices.
Like most areas of Maui, there are tons of restaurants in the Kihei area. All of the resorts at Wailea have several restaurants of varying types and prices (usually high). You'll go broke if you try to hit them all. Get a good guide book (like Maui Revealed) and pick one special one. There are lots of casual places that may be more expensive than what you're use to, but they won't break the bank.
Here are the places we checked out:
Lu Lu's: On the second floor of one of the buildings at Kihei Kalama Village shopping area, this place turned out to be a pleasant surprise. It has a typical bar and grill set up with a big bar area and outdoor seating for dining. Being on the second floor allowed us to look above the parking lots and bustle of Kihei Road out to the sunset on Kamaole Beach. We just missed $1 Mai-Tai happy hour but even for $3, they were great! The food was fairly typical Hawaiian bar and grill fare (meaning they have better fish than a joint in, say, Cleveland). My wife had a terrific guacamole burger and our son enjoyed a huge plate of popcorn shrimp (they were pretty good sized for "popcorn"). I had a caesar salad with seared ahi ,which was done perfectly. Topping that off with a singer/guitarist who knew a number of Steve Earle songs and friendly service made this a great place for a casual meal.
Pita Paradise: Located in a small building also in the Kihei Kalama Village, this greek style restaurant was also very enjoyable. While our son was enjoying mac and cheese back at the condo, we dined on hummus and separate pitas filled with Australian free range lamb and fresh uku (grey snapper). How fresh was the uku? The owner caught it himself that day! The pitas were good sized and reasonably priced. We finshed with an excellent homemade baklava ice cream cake. Friendly service, too.
Thai Chef: We had a craving for Thai food and Thai Chef was nearby, in a rather dreary location in the back of the not so great Rainbow Mall. The food was a lot better than the location. We had excellent Panang curry with beef and Pad Thai with chicken. The portions were slightly smaller than what we get at our local Thai restaurants so you may want to order one extra dish if you're hungry. We went just as they opened so we were the first ones in the fairly spacious dining room. They sat the next two couples that came in at the adjacent tables on either side of us while the rest of the tables sat empty. More efficient, I guess.
The candy dish at the cash register had root beer barrels, which you don't see every day in a Thai restaurant (or anywhere else for that matter).
Longhi's at Wailea: We decided to wander the upscale Shops at Wailea and have dinner there. There were four choices, but which one to pick? Ruth's Chris Steakhouse? Nah, we have one of those at home. The Cafe at Tommy Bahamas? Sorry, I don't eat at clothing stores, except maybe at the original Nordstroms (in fairness, a timeshare rep at the Embassy Resort told me it was pretty good). How about Cheeseburgers, Mai-Tais, and Rock N Roll? Despite the cumbersome name, it seemed the most popular place in the shopping center, most likely because it was also the cheapest. There was at least a 25 minute wait for a table. Jimmy Buffet may not sue them (like he did their sister restaurant Cheeseburger in Paradise in Lahaina), but we decided we didn't want to wait. So we wandered over to Longhi's at Wailea. Although we had never been to the original Longhi's in Lahaina, it is well known and was always crowded. They don't post the menu outside like most restaurants in the area but have it available for viewing at the reception desk. I guess they figure once you're in, you won't change your mind and leave. While my wife was perusing the menu, I wandered over to look at a display case on the wall. It had three different colored polo shirts that I presumed had the restaurant logo on it and were available for purchase. The left and right polos indeed had Longhi's script logo embroidered on the sleeve. But the center shirt was instead embroidered in the same lettering style with (I swear I am not making this up) "Whatthef*ck", except it used the letter "u" instead of a "*"! Very, very strange for a high end restaurant. I quickly returned to the reception desk so that my wife and son wouldn't wander over to see what I was looking at. Just to make sure I wasn't nuts, I later checked their website and sure enough, they not only sell those shirts but deem them "The Famous Whatthef*ck" shirts! While the phrase may have worked for Tom Cruise in Risky Business, I don't get it here.
The hostess (how does she walk in a dress that tight?) then showed us to a nice table with a great view of the setting sun over Wailea Beach. Our VERY casual waiter wandered over and proceeded to give us details of some of the menu items although sometimes he didn't seem too sure of what he was talking about and had to consult the large book of Longhi's history and recipes that is conveniently placed on the table. Apparently at the Lahaina location, they don't even give you a menu - the waiter recites the items to you. I don't think our guy could've done that (maybe that's why he was at this location instead). While we were deciding, we were served an odd pizza crust type bread, half with tomato sauce, the other half with jalapenos. It was good but seemed out of place. We then shared an excellent caesar salad. For our entrees, our son selected their calamari appetizer, my wife went with Penne Puttana, and I had their signature Ahi Torino. The calamari got a thumbs up, and the pasta was plentiful and wonderfully spicy. My ahi, marinated in olive oil, garlic and basil, rolled in macadamia nuts and sauteed, tasted excellent but it's presentation reminded me of the "breaded veal cutlet" we used to get in the high school cafeteria. It just laid there in a slab on the plate with a thin lemon slice on top and a lonely sprig of parsley lying next to it. With so many wonderful presentations in their book, it seemed a very strange look for one of their signature items.
We somehow managed to save room for dessert and selected an excellent raspberry and blackberry glace off the dessert tray. It turned out to be a nice way to end a rather surreal meal.