What could be as good as relaxing on the gorgeous beaches of Wailea? Dining at one of the area’s top-notch restaurants, that’s what.
Gannon’s Restaurant in Wailea
Gannon’s, voted one of the Top 100 Best Outdoor Dining Restaurants in the country, has terrific ambience; its lanai dining offers a panoramic view of the ocean and of tropical sunsets beyond the coconut trees.
Chef Beverly Gannon, who also runs the restaurant Hali’imaile General Store, serves Hawaiian regional cuisine — contemporary dishes inspired by fresh local ingredients. There’s an extended happy hour at the restaurant’s Red Bar and live music on the weekends. And if you’re around at the right time, check out their Movies Under the Stars events.
Monkeypod Kitchen by Merriman
Popular “locavore” chef Peter Merriman, whom the Los Angeles Times called the “Pied Piper of Hawaii Regional Cuisine,” owns the upscale Wailea restaurant Monkeypod Kitchen.
Merriman, a member of the Hawaii Restaurant Association Hall of Fame, features locally sourced ingredients, including fresh fish that comes in on the boat each day.
The restaurant is known for its Monkeypod Mai Tai, which has a passion fruit foam; the poke tacos are also delicious. They hand toss pizzas in the kiawe-wood pizza oven. (Would you choose the Proletariat pizza, with pepperoni, or the Bourgeois pizza, topped with lobster and wild mushrooms?)
There’s also live music and 36 craft brews on tap that are always served at 29 degrees.
Wailea Kitchen and Tap
“A view to dine for,” boasts Wailea Kitchen and Tap, and it’s true. The restaurant serves cold drinks and tasty food in an open-air setting with unbeatable ocean and sunset views.
Arrive in time to hear live music, coined the “Sunset Sessions.” And note the restaurant’s sense of humor, too: The appetizer menu includes Lord of the Wings (classic Buffalo or Asian-sesame wings) and Lord of the Fries, which come either classic or with salt and vinegar. Entrees include burgers, sandwiches, poke bowls and fish tacos, and prices are reasonable.
Located at The Shops of Wailea, this family-owned restaurant features Mediterranean cuisine for breakfast, lunch and dinner. Note that Longhi’s Wailea has its own in-house bakery where the staff creates all their own breads, pastries (like the amazing cinnamon rolls) and desserts like their signature hot chocolate soufflé.
For breakfast try the Lobster Benedict, Lox Benedict and Crab Cakes Benedict. Longhi’s cuts their bacon in thick slabs, and they also serve fresh coffee by local Maui growers. Dinner appetizers include the Artichoke Longhi, with melted lemon butter and fresh-grated Parmigiano-Reggiano. There’s an award-winning wine list, and the seating is open air.
Don’t let the fact that it’s located in a strip mall throw you! Matteo’s Osteria, just below the Residence Inn Maui Wailea, won a 2016 award for Best Italian Food on Maui. Chef Matteo Mistura, who was born and raised in Liguria, Italy, serves locally sourced Italian cuisine, and Matteo’s has the island’s largest selection of wines by the glass. There’s even a happy hour from 3 p.m. to 6 p.m. on weekdays.
Here’s your perfect Matteo’s evening: Sit on the patio, order the restaurant’s signature lasagna dish (it’s served in a crock) and finish off your meal with tiramisu.