Nestled on the southern shore of Maui, Wailea is an area that’s notorious for beautiful beaches and high-end resorts of the Relais & Château and Four Seasons varieties. Wailea is a place you go to escape, and the last thing on your mind should be how to get to dinner. Luckily, the Wailea resort community has some stellar, authentic restaurants of its own—all within minutes of your beachside lounge chair. Here, the four you should try.
1. Ka’ana Kitchen
Opened in 2013, Ka’ana Kitchen is a relative newcomer to Wailea’s high-end dining scene. Maui native Chef Isaac Bancaco worked in Boston with Ming Tsai and in Los Angeles with Roy Yamaguchi before returning home to the island. Ka’ana’s sleek atmosphere, along with its big open kitchen, farm-to-table cuisine, global wine list, and family-style service, puts this restaurant on par with those in food-obsessed cities like New York and San Francisco.
The menu goes out of its way to highlight local fishmongers, farms, and meat purveyors. Noteworthy “Ka’ana Classics” include grilled octopus and abalone risotto and local fisherman Barry Masuda’s Maui-caught fish. A meal here is worth the splurge for special occasions. Pro-tip: Opt for the chef’s counter where you can watch the culinary acrobatics and chat with the kitchen team.
2. Monkeypod Kitchen
Located within sight of the Pacific, Monkeypod is a boisterous indoor-outdoor hangout where locals are widely represented. It doesn’t look like much from the outside, but the expansive indoor space and outdoor patio make up a quintessential resort town watering hole. Both locals and visitors go for one of the two nightly happy hours, where appetizers are half off, wood-fired pizzas are $9, and drinks are discounted. Highlights include the lobster deviled eggs, garlic truffle oil fries, wood-roasted chicken wings, and Hamakua wild mushroom pizza. They’ve got 36 beers on tap, ranging from local Hawaiian breweries to Belgian and German imports, and the mai tai with lilikoi foam rivals any other mai tai on the island. For dessert, there’s a lineup of cream pies, including coconut cream, an island favorite.
3. Kō
Adjacent to the Fairmont’s pool with the ocean viewable in the distance, Kō provides the ideal mix of casual and elegant that’s perfect for dressing up for dinner but laid-back enough for a quick afternoon respite from the beach. This is the place to take anyone with a dietary restriction, because the flexible menu accommodates anything from vegan to non-dairy to gluten free—and every meal still comes out tasty.
The food honors the islands’ diverse histories and Hawaiian, Chinese, Filipino, Portuguese, Korean, and Japanese influences. Favorite dishes include the timeless tuna poke, ginger-hoisin barbecue pork chop, and lobster tempura. The circular bar in the center of the restaurant hosts a daily happy hour offering $13 pupus (appetizers) such as crispy calamari, poke, sushi, and flatbreads alongside mai tais, daiquiris, and a rum-spiked Lava Flow.
4. 5 Palms Restaurant
Sitting practically on the sand of Keawakapu Beach, 5 Palms is the place to take in spectacular ocean views and unrivaled sunsets. Aim to arrive at this beachfront oasis before sunset to scope out a table and settle in with an Arnold Palmer or something stronger.
Happy hours run from 3 to 7 p.m. and 9 to 11 p.m., and tables get snagged quickly. The restaurant is also a standout for breakfast—tableside whale sightings are the norm during whale season—and the crab-and-avocado omelet is a year-round staple.
