Wailea Dining with Tweens + Teens: What’s Actually Worth the Reservation
Maui has so many restaurant options it’s almost impossible to cover them all, so for this post, I’m focusing mainly on Wailea and where we actually ate on our last trip.
Our main dinner reservations were:
Grand Wailea Luau
Humuhumunukunukuāpuaʻa
Spago Maui
Nobu Grand Wailea
Champagne and drinks at the Fairmont Kea Lani lobby bar, followed by dinner at Olivine back at the Grand Wailea
Lunch was usually the much more casual and off the cuff: pool service, the Napua Lounge, or the hidden taco truck (still underrated).
We also spent a day Upcountry (more on that in the activities post) and had a great casual meal at Polli's Mexican Restaurant in Makawao.
Some dinners were absolutely worth the splurge. Some were… expensive lessons.
Nobu: Amazing Food, Terrible Ending
Nobu restaurants have always been one of our favorites, and we’ve been to several locations, so we were excited for this one.
The good news: the food was excellent.
Yes, it’s expensive—but the service was polished, the sushi was fantastic, and the overall experience felt special.
We loved:
sushi rolls
hamachi
black cod
wagyu
My daughters were perfectly happy with:
California rolls
vegetarian rolls
edamame
miso soup
My husband was mildly offended that he had to cook his own wagyu at the table. I, however, considered that part of the entertainment.
It was so good we booked it twice.
And then…the second visit ended with what may have been one of the more unnecessary luxury hotel restaurant confrontations I’ve ever had.
We had ordered a nice bottle of wine, and by the end of dinner there was still a generous amount left. We were staying at the hotel, charging everything to the room, and honestly just heading upstairs to watch a movie with the kids.
Without asking, the waiter poured the rest of the bottle into our glasses instead of offering to cork it. Fine.
We walked out with the glasses, stopped for thirty seconds to take a nice couple’s photo in the lobby…and suddenly the bartender came running after us like we had dined and dashed.
Very loudly. In front of everyone.
Apparently, I was now an outlaw because I had committed the crime of trying to take expensive wine in a proprietary glass to my hotel room.
He insisted I either come back and finish it immediately or pour it into a plastic cup.
I explained that I did not want to shotgun wine, nor did I want to drink very good wine out of a plastic cup. Especially inside the hotel where I was staying.
He was not amused. At that point, my husband took over and I took the kids upstairs.
Suffice it to say… I don’t think we’ll be rushing back to Nobu.
Maybe that sounds picky. But when you’re paying that kind of money, and the waiter himself creates the situation by pouring the remaining wine, I don’t think public embarrassment in the middle of the lobby should be part of the experience. I also think at this price point, there should be some flexibility afforded by the restaurant.
The Grand Wailea Luau: Beautiful, But Hard to Justify
This is marketed as one of the more luxury luaus on the island, and to be fair, there were definitely positives.
Unlike many luaus, this is not a buffet—it’s a seated dinner, which I appreciated.
The professional photos were actually beautiful. The show was strong, and of course, the fire dancer completely stole the show.
That said…I’ve seen luaus that were equally impressive for significantly less money.
The open bar was included, but the drinks themselves were not exactly memorable.
And for a family of four? You’re looking at close to $2,000.
Yes, really.
You can pay slightly less if you’re willing to skip having your own table, but when I say “slightly,” I mean maybe 10%.
Wah wah.
Luaus are part of the Hawaii experience, and I do think you should do one.
I just wouldn’t necessarily do this one again.
My recommendation:
save money and go to one at the Wailea Beach Resort - Marriott, Maui, or spend a little more and go full luxury at the Andaz Maui at Wailea Resort.
Spago: Absolutely Worth the Splurge
Spago Maui was the highlight of the trip. No question.
Located at the Four Seasons Resort Maui at Wailea, it absolutely delivered.
We managed to grab last-minute reservations and got there right at sunset.
Were there technically better tables? Probably.
Did I care once I saw the ocean view and the sky turning pink? Not at all. For a last-minute reservation, I was thrilled.
The service was top-notch and the food was incredible.
This is the kind of dinner where the splurge actually feels justified. Spago is not cheap. But unlike some places, you leave feeling like yes—that was worth it.
That’s rare.
Humuhumunukunukuāpuaʻa: Stunning Setting, Disappointing Dinner
This one hurt because I wanted to love it. The restaurant itself is gorgeous.
It sits over the lagoons, overlooks the ocean, and feels like one of those “this is why we came to Hawaii” places.
And the bar? The bar is one giant aquarium. Not behind the bar. Not next to the bar.
The actual bar where you put your drink down is an aquarium. Very cool.
Breakfast here was great, especially using the Amex breakfast benefit.
Small note: on less busy weekdays, the omelet station sometimes disappears. Not tragic, but I do love an omelet station.
Dinner, unfortunately, was a different story. My daughters' food was bland and forgettable.
The seafood tower was good.
But then my husband’s and my entrees took over an hour.
By that point, the kids were tired, hungry, and heading straight into vacation meltdown territory. We ended up canceling the entrees and leaving.
Very disappointing for a place we had been genuinely excited about.
Beautiful setting.
Not a repeat reservation.
Olivine: Quiet Surprise of the Trip
This was our final dinner, and honestly, one of the nicest surprises. Before dinner, we walked over to the Fairmont Kea Lani for drinks.
Wow. They have really stepped up their renovation. The property looks beautiful and the service was excellent. It definitely made us rethink where we might stay next trip.
Then we took a quick five-minute Uber back for our reservation at Olivine.
It was casual, easy, and exactly what we needed on the last night before an early flight. The food was great, service was solid, and the view was beautiful.
Not every dinner needs to be a major event. Sometimes the best meal is the one that feels easy.
Great value.
Great experience.
Would absolutely recommend.
Final Thoughts
Not every Maui dinner needs to be a massive reservation battle.
Some are worth the splurge. Some are worth skipping. And sometimes the best move is grabbing tacos by the pool and calling it a win.
If I were booking again:
Book early:
Spago
Do once:
a luau
Skip the drama:
Nobu round two
And never underestimate:
the hidden taco truck
the Napua Lounge
and a restaurant with solid service on the last night of vacation