Best Restaurants in Wailea, Maui: A Local's Guide to South Maui Dining

Where Wailea Actually Is (and Why It Matters for Dinner Plans)

Wailea sits about 15 to 20 minutes south of Kihei along South Kihei Road, which turns into Wailea Alanui Drive once you pass the Fairmont and the Makena turnoff. That short drive is the single most useful thing to know when planning meals. If you are staying at unit 711 at 3559 Lower Honoapiilani Rd #11, you are close enough to grab a 7 p.m. table in Wailea and still be back on the lanai in time to watch the last of the sunset light up Lanai and Molokai across the AuAu Channel.

Parking is the other practical detail. Most Wailea resorts validate for restaurant guests, but the garages fill up between 5:30 and 6:30 p.m. Arrive 15 minutes early and you will save yourself a slow lap around the Shops at Wailea.

The Oceanfront Splurges Worth the Money

Wailea is the place on Maui where a special-occasion dinner actually delivers on the view. Two names come up again and again.

Humuhumunukunukuapua'a at the Grand Wailea is built over a saltwater lagoon with fish circling beneath the walkways. Thethatched-roof setting is pure theatre, and the menu leans on Hawaiian seafood with a Polynesian tilt. Go for the macadamia-crusted fish and the lobster tempura. Reserve three to four weeks out for a sunset seating.

Ko at the Fairmont Kea Lani is the more refined of the two, serving plantation-era Hawaiian food with real depth. Order the kalua pork spring rolls to start, then the seafood laulau. The outdoor tables face west, so the 5:45 p.m. slot in winter and the 6:15 p.m. slot in summer are the ones to chase.

Both run $60 to $120 per person before drinks. If that is your once-a-trip dinner, either works. If you want the view without the price tag, read on.

Mid-Range Picks That Locals Actually Book

Not every great meal in Wailea costs resort money. These three hit the sweet spot between quality and value.

Monkeypod Kitchen is the reliable crowd-pleaser. The mai tais are made with fresh-squeezed juice and the wood-fired pizza and fish tacos are consistent. Happy hour from 3 to 5 p.m. is the best deal in Wailea, with half-price appetizers and discounted drinks. No reservations for the bar area, so walk in and take your chances.

Longhi's Wailea covers breakfast through dinner in the Shops at Wailea. The lobster benedict at brunch is a genuinely good call, and the courtyard seating is quieter than you would expect. It is also one of the few Wailea spots where walk-ins are realistic before 6 p.m.

Mulligan's on the Blue sits above the Wailea Blue golf course and serves solid pub food with a sunset view that competes with the resorts. The fish and chips and the prime rib sandwich are the standouts. Live music most nights, and no dress code.

Casual Bites, Plate Lunch, and Takeout

Some nights you want to eat in shorts and be back at the condo by 7:30. Wailea handles that too.

Island Gourmet Markets at the Shops at Wailea is the workhorse. Hot plate lunch, poke by the pound, fresh sushi rolls, and a wine selection better than most mainland grocery stores. This is where you build a lanai dinner: grab a poke bowl and a bottle of something cold, drive the 15 minutes back to Kihei, and eat outside while the sky turns orange over Lanai. It beats most restaurant views on the island.

808 Deli in Kihei, just up the road, makes the best sandwiches on this side of the island and will pack them for a beach day. The turkey avocado and the lilikoi cheesecake are the two things to order. Call ahead if you are going between 11:30 a.m. and 1 p.m.

Paia Fish Market has a Wailea location now, and the ono fish tacos are the same ones people drive to the north shore for. Portions are large enough that two plates feed three people.

What to Order (and What to Skip)

A few honest notes that save first-timers some money:

• Order the fresh catch. Ono, mahi mahi, ahi, and monchong rotate daily. Ask what came in that morning rather than defaulting to the menu photo.
• Skip the $22 resort cocktails if you are not staying on property. The same mai tai costs half as much at Monkeypod and tastes better.
• Book sunset seatings early. Wailea's west-facing restaurants sell out three to four weeks ahead in winter, when sunset lands around 5:45 p.m. and everyone wants that slot.
• Do not skip dessert. Hula pie, lilikoi cheesecake, and anything with macadamia nut are worth the calories.

If you would rather skip the reservation game entirely, the kitchen at our oceanfront condo in Kihei is fully stocked, and the grill area downstairs is rarely busy on weeknights. Plenty of guests end up cooking three or four dinners in and spending their restaurant budget on one big Wailea night instead.

Timing Your Wailea Dinner Around the Rest of Your Trip

Wailea pairs naturally with a beach day at Makena or a snorkel run to Ahihi-Kinau, since both are just south of the resort row. Book your dinner for the way back rather than making a separate trip.

From November through May, whale season overlaps with sunset dining. Ask for a table facing west and you will often see humpbacks breaching in the AuAu Channel while you eat. The view from a Wailea table is good. The view from our lanai, 35 feet of west-facing glass looking out at Lanai and Molokai, is arguably better, and the sea turtles on the shoreline below are a bonus no restaurant can offer.

Want more options closer to base? Our companion guide to restaurants in Kihei covers the spots within walking distance of the condo, and the South Maui beach guide maps out which shore to pair with which dinner reservation.