Updated: May 21, 2015
Wailea Restaurant Guide:We recently took a trip to Maui (December 2010) and stayed at the Grand Wailea Resort on the southwest section of the island. Wailea is a beautiful area and the resorts are spectacular to say the least. The Grand Wailea being perhaps the largest of the bunch in Wailea and they offer a huge pool complex along with a perfect beach just steps away. The unfortunate part of staying at such a grand resort is that the food prices are very expensive. After paying $300+/night to stay there it's hard to swallow a $80/breakfast, $120/lunch and $200/dinner bill everyday. I'm not cheap when on vacations, but those prices could ruin any family of 4. We requested a refrigerator in our room so that we could keep drinks and snacks on hand throughout the day but we also ventured to the local restaurants as a way to get out of the Grand Wailea - mostly for dinners. The good news is that literally 2 minutes away are the Shops at Wailea which is a nice shopping mall with upscale clothing stores and lots of restaurants to choose from. There is Cheeseburger Island Style, KAI Wailea Sushi & Japanese Tapas, Longhi's, Ruth's Chris Steakhouse, Tommy Bahama's Cafe, and Lappert's Ice Cream shop. A good variety for kids and adults.
Not too far up the road is the town of Kihei which offers even more casual dining - Maui Tacos, small eateries, coffee shops, pizza joints, etc. Food is notorious for being expensive anywhere on the islands (Maui, Kauai, Oahu) as much of the food is shipped in. Resorts are definitely not the place to eat unless you have an unlimited budget. We spent a few nights eating at the Grand Wailea (see below), but we also wanted to try different restaurants in Wailea and even in Kihei. Wailea is small and most of the restaurants are fairly nice. The Four Seasons Resort has the #1 rated restaurant per TripAdvisor called the Ferraro's Bar e Ristorante, we did not get to try that one although online reviews for it are very positive. Spago (Four Seasons) and MALA (Wailea Beach Marriott Resort) are also rated highly, but those are at resorts and are fairly pricey as well. In the next section we will go into the various restaurants that we ventured to while we stayed in Wailea.
Best Restaurants in Wailea, Maui:There are lots of choices and some are better values than others. Keep in mind you are in a tourist spot on a tropical island so no meal will be cheap by our standards on the mainland. These are the places we ate at - what we ordered, how the service was, prices, would be go again.
Longhi's Restaurant - We ate at Longhi's in Lahaina last year and this year we went to the location in Wailea. Just pop into the Shops at Wailea and Longhi's is downstairs (below Tommy Bahamas). The service was better than most places we ate at and they were decorated for Christmas with a nice looking tree that we got a picture in front of (ended up being our X-Mas card). The Wailea location is open for breakfast, lunch, and dinner. You can view their website at http://www.longhis.com/. We had the Filet Mignon, two kids plates, a combination seafood plate, and a chocolate souffle for dessert. Their dinner menue includes other items like pasta, fish, meat, and chicken. All the menus can be found on the website. Prices were high compared to most spots we ate at, but the food was excellent and the outdoor ambiance was just perfect on a warm evening. The waiter brought out the kids food first - this was the only place that did this favor on the entire trip. We would definitely go again.
Cheeseburger Island Style Wailea - This casual burger joint was opened up in 2001 and it's another good spot if you have kids. The menu is loaded with various combinations for burgers and should satisfy anyone. There are also appetizers like calamari and salads to choose from. The meal was basic but the kids liked the decor in the restaurant and the wait staff was very accommodating. Prices are about $10 to $15 for a burger. They are open for breakfast, lunch and dinner. We had burgers and fries along with a few beers (adults not the kids). our kids split an order of sliders (with kobe beef). Food was good and the total tab for dinner was less than $70. Would go again in the future.
Kai Wailea Sushi - Fresh fish is one thing that Maui does well and this sushi spot serves up some cool dishes. The location is right within the Shops at Wailea. Get a Sake Flight or fresh sushi rolls of all your favorites plus sashimi. My wife did the Sake tasting and thought it was great. We shared some sushi and tried the appetizer of Sashimi Trio. The Rock Shrimp tempura roll was delicious. Sushi is expensive no matter where you go and our total bill with drinks (and 2 kids eating) was just over $100. The service was a bit much for us as the waiter literally stood a few steps from our table listening to our conversation as if he had nothing else to do. Otherwise the food was good and the drinks (local beers) were even better. Would try it again, but this time without the kids. Their website is at http://home.kaiwailea.com.
Tommy Bahama's Restaurant & Bar - Ok, so this one surprised us a bit. I knew there was a store for Tommy Bahama in Wailea but the restaurant was news to me. Our friends had eaten there last year and they told us to give it a try. It's located right above Longhi's in the Shops at Wailea mall. Interesting decor in the restaurant, although a bit dark for my liking. We started with a few drinks (Mojito and Leward Lemonade) and they were good. I had the crab bisque and the 1/2 rack of ribs. Both were quite excellent. My wife had the crab cakes and a caesar. Nothing special per her opinion. The kids ate things like hot dogs and chicken fingers. Not a bad spot, but probably not the type of place we would go again. Prices - total bill was $120 (ribs were close to $30) which I felt was too high for what we got. The website can be found at http://www.tommybahama.com/TBG/Stores_Restaurants/Restaurants/Wailea.jsp.