Prices in Wailea are much higher than in other parts of the island, and double the cost in Kihei. You’re often paying for master chefs, exceptional service, and unparalleled ambience in world-class resorts, which oftentimes makes it worth the experience. However, if you venture outside of the resort areas, there are also numerous places for a filling and affordable meal.
At the Four Seasons, Duo (3900 Wailea Alanui, 808/874-8000, 6:30am-11am, 5:30pm-9pm daily, $30-50) ranks in the upper echelon of fine island cuisine. The dinner menu is dominated by steak and seafood options such as Brandt True filet mignon and shiso panko-crusted ahi. For something light, try the lobster bisque. The breakfast buffet is lauded as the best in Wailea.
At the beautiful Grand Wailea, Humuhumunukunukuapua‘a (3850 Wailea Alanui Dr., 808/875-1234, 5:30pm-9pm daily, $30-49) is not only one of the hardest restaurants to pronounce, it’s also one of the most popular. Named after the state fish, “Humu” sits in a thatched-roof Polynesian structure afloat on its own million-gallon saltwater lagoon. Large plates include the famous Hawaiian spiny lobster dish, where you can choose your lobster from the lagoon, as well as crispy mahimahi or fresh opakapaka. The sunset view looking over the lagoon is the classic image of paradise. The third Thursday of every month is the Ka Malama Dinner ($150), where the head chef, Mike Lofaro, teams with the resort’s Hawaiian Cultural Ambassador to create a meal that’s based around the traditional Hawaiian lunar calendar. The concept for the meal was so successful that it led to a television show, Search Hawaii, that’s a fusion of culture and food.
For more plantation-inspired cuisine, Ka‘ana Kitchen (3550 Wailea Alanui Dr., 808/573-1234, 6:30am-11am and 5:30pm-9pm daily), inside the Andaz, is popular for both breakfast and dinner, where the chefs prepare food in an open-air kitchen you can see from your table. For breakfast, try the kalua pork Benedict with ponzu hollandaise ($22), and for dinner, abalone risotto ($31) or tender wagyu beef cheeks ($47).
In the Fairmont Kea Lani, Nick’s Fishmarket (4100 Wailea Alanui Dr., 808/879-7224, 5:30pm-9:45pm daily, $30-50) has whitewashed walls, a vine-covered trellis, and Mediterranean ambience. Selections include opah, mahimahi Kona kampachi, and Moroccan spiced salmon, along with creative sides like wasabi mashed potatoes and mango peppercorn chutney. Reservations are recommended.
Wailea’s best pizza, Manoli’s Pizza Company (100 Wailea Ike Dr., 808/874-7499, 11:30am-10pm daily, $16-22) is walking distance from many of the hotels, across from the Shops at Wailea. It serves 14-inch thin-crust pizzas, with organic and gluten-free options and toppings that include shrimp, pesto, kalamata olives, artichoke hearts, and feta cheese. There are salads, pasta, and a selection of 20 wines, and specials at happy hour, 3pm-6pm and again 9pm-midnight daily.
At the luxurious Four Seasons Resort, the tables at Ferraro’s Bar e Ristorante (3900 Wailea Alanui Dr., 808/874-8000, 11:30am-8pm daily, $30-50) are close enough to the ocean that you can dine to the sound of the waves. Clink glasses beneath the stars and savor the authentic cucina rustica while listening to a live violin. Lunch is more casual, with wood-fired pizzas, and why not some pinot gris?
Up on the hill, The Restaurant at Hotel Wailea (555 Kaukahi Rd., 808/879-2224, 5pm-9:30pm daily) has a sweeping sunset view from the balcony looking over Wailea, and tremendously fancy Italian fine dining with a wine list that runs for miles. The service is spectacular, and much of the produce and herbs for the dishes are sourced on the property. Reservations are advised, and the menu changes seasonally.
The first restaurant you’ll encounter in Wailea approaching from Pi‘ilani Highway is Monkeypod Kitchen (10 Wailea Ike Dr., 808/891-2322, 11:30am-10:30pm daily, $13-35), the brainchild of renowned Maui chef Peter Merriman. Ingredients are all sourced locally, supporting sustainable farming and ensuring fresh, healthy meals. Dinner options range from sesame-crusted mahimahi to bulgogi pork tacos in an Asian pear aioli, or an organic spinach and quinoa salad big enough to share. The craft beer list is the best in Wailea. To save a few bucks, visit during happy hour, 3pm-5:30pm and again 9pm-11pm daily, when appetizers are 50 percent off and pizzas are only $9.
For a quick meal in Wailea, there are thankfully some affordable options. At the Island Gourmet Market (3750 Wailea Alanui Dr., 808/847-5005, 6:30am-10:30pm daily) inside the Shops at Wailea, you can find breakfast ($6-8), chili and rice ($6) for a filling lunch, açaí bowls ($7) that provide a little health, and poke bowls ($7) for a fish power lunch. There’s a coffee shop inside the store as well as a decent wine selection.
Up the hill, at The Market Maui (10 Wailea Ike Dr., 808/879-2433, 8am-7:30pm daily), the sandwich, smoothie, and coffee offerings are a little more gourmet, with prices that are reasonable for Wailea. Recharge with a Kumu Kale smoothie ($8), or sink your teeth into sourdough topped with cured meats, olives, and horseradish ($12). The Market is located inside the Wailea Gateway Plaza, directly under Monkeypod.
Excerpted from the Tenth Edition of Moon Maui.