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Managed expectations: A review of the Grand Wailea Maui, A Waldorf Astoria Resort

Sept. 12, 2020
18 min read
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Editor’s note: This review covers a stay that took place before the onset of the COVID-19 pandemic. The state of Hawaii remains closed to tourists. It recently pushed back the targeted reopening date to Oct. 1 at the earliest.

Despite the state's closure to tourism, Hawaii remains an immensely popular destination for travelers from all over the world, and we hope this review helps you make decisions on any travel you may be planning for once it's safe to do so once again.

This winter, before "coronavirus" was even a word in our lexicon, I escaped Montana with a trip to Maui. Having been to Kauai on a previous trip, I was excited to visit a new Hawaiian island destination that my friends and co-workers have raved about for years.

I had been eyeing a stay at the Grand Wailea Maui, A Waldorf Astoria Resort, so when I found award availability for January 2020 I jumped on the opportunity to book. Here's more about our five days at the resort.


I booked the room at the Grand Wailea through Hilton's website, which made the process simple. Award nights can be had for as little as 95,000 Hilton Honors points per night but can be difficult to find at the Grand Wailea, especially if you're booking a stay longer than three nights. I used the 5th-Night Free benefit, so I spent a total of 380,000 points for our five-night stay. In addition, I didn't have to pay the $40 nightly resort fee because it was an award stay, so my points covered more than just the nightly rate.

Cancellations are allowed without penalty up to 14 days prior to arrival, so you can reserve a room when you find availability even if you aren't sure the dates will suit your schedule.

Related: Best times to visit Hawaii

I applied for the Hilton Honors American Express Aspire Card with this particular trip in mind. It was well worth it. I booked the least expensive Terrace View room but was upgraded to a Garden View room. The information for the Hilton Aspire Amex card has been collected independently by The Points Guy. The card details on this page have not been reviewed or provided by the card issuer.

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During my stay, the cash price of a Garden View room was $600+ per night, so I got a solid 0.7 cents per point for my redemption -- slightly above TPG's latest valuation of 0.6 cents per point for Hilton points. Rates can easily surpass $800 per night, depending on the time of your visit, so using your points for a stay can certainly offer a good value.


The Grand Wailea is located near many of the island's other upscale resorts, like the Andaz Maui, Fairmont Kea Lani and Four Seasons Maui Resort.

The hotel is about a 30-minute drive south from the Kahului Airport (OGG), with the closest town being Kihei, which is halfway between the property and the airport.


When you arrive at the Grand Wailea, there's no doubt you'll be impressed by its grandeur -- from the beautifully manicured grounds to the large waterfall you pass just before reaching the valet.

Valet service is a whopping $40 per night, and having done some internet sleuthing before our arrival, it didn't seem like there was any way around that cost. In fact, I'd been told by a friend who'd recently stayed at the resort that she had no luck finding free parking nearby. So, resigned to the fact I'd be spending $200 on parking during the stay, I handed my keys to the valet -- but more on that later.

As we walked inside, we were presented with leis and then directed to the check-in area.

At check-in, I was offered the option to upgrade to the Napua Tower. Although it was tempting, I didn't think it was worth the $175 extra per night. Instead, even though I had booked a Terrace View room, I was upgraded to a Garden View room, a perk of my Diamond Elite status from my Hilton Honors Aspire Card from American Express.

If you decide on the Napua Tower, you'll have access to two private lounges that offer free continental breakfast, light snacks and a full bar. Of course, you'll also have amazing views from your room. Napua Tower could make sense if you spend a lot on alcoholic beverages. However, I overheard a number of guests commenting that the continental breakfast and snacks in the lounge were rather lame -- think Ritz Crackers and cubed ham.

Plus, after getting a chance to explore the hotel, I can honestly say I think that certain Garden View rooms are better-suited for anyone traveling with kids because you don't have to wind your way through the hotel to get to the pools and the beach. You essentially have a playground right out your back door.

The view from the rear of the hotel looking out toward the ocean is truly spectacular. Sure, you'll likely see this exact picture in any review of the Grand Wailea, but seeing it for yourself will really knock your socks off.

A tip to avoid the valet fee: I actually did find free parking about a mile south of the hotel on Kaukahi Street near the Fairmont Kea Lani. The best part is, you can walk the paved Wailea Beach Path that offers incredible ocean views almost the entire way between the free parking area and the hotel. After you park your car on Kaukahi Street, head to the entrance of the public Polo Beach Park and there you'll find the path.


Before booking our stay at the Grand Wailea, I had done some research so I didn't have high expectations for our room. I'd read reviews that said the rooms are dated and worn, and having stayed there now I'd have to agree. Everything from the tile in the bathroom, to the furniture in the bedroom and the colors on the walls seems tired. Still, it has everything you need for a comfortable stay.

Upon entering the room there is a small hallway and the room's only closet.

There was plenty of room for our two suitcases and clothes that needed to be hung. The safe is inside the closet.

The bathroom is really spacious and I appreciated the fact that the toilet is behind its own door.

There's a bathtub and a large shower with a glass enclosure that helps make the bathroom feel even roomier.

There is only one sink but the vanity is plenty large enough and provides ample room for storage. The resort stocks the bathroom with toiletries from Spa Grande, the hotel's world-renowned spa.

A small alcove near the bathroom houses a Keurig and a minifridge.

Extra coffee and tea pods were always available from housekeeping when we asked.

At the end of the short hallway is the bedroom, which I found to be simple but comfortable. It certainly isn't the most beautiful room I've ever stayed in, but it didn't feel cramped and the beds and bedding were cozy.

A flat-screen TV is installed above the room's only dresser.

And a decent-sized desk is in the corner of the room.

I especially liked having a Garden View room because my daughter enjoyed playing in the grassy area just off the lanai.

As you can see, the room opens onto the resort with tons of space to run around. Although you can't see it in the photo, there is a pool and hot tub just behind the trees -- essentially just steps away from our porch.

Although the room (and honestly the whole hotel) is far from the most luxurious, we didn't spend much time inside anyway. There's so much to see and do at the resort and on Maui, in general. However, given the cost of the hotel and the Waldorf Astoria name, I can understand how some guests might be disappointed in the quality of the space.

Related: How to use Hilton points for a Hawaiian vacation

Food and beverage

There are a few different dining options at the Grand Wailea, ranging from casual spots like the poolside Volcano Bar & Lounge to the resort's high-end restaurant, Humuhumunukunukuapua'a -- or Humuhumu for short.

Once again, because of my Diamond Elite status (from my Hilton Honors Aspire Card from American Express), we were offered free continental breakfast every morning, with the option to upgrade to the full breakfast buffet for $19 per person. Without Diamond Elite status the buffet costs $47, so it's easy to see how valuable elite perks can be. Because children, or keiki (meaning child in Hawaiian), ages 5 years and younger dine free at the breakfast buffet with a paying adult, upgrading to the full buffet was a no-brainer.

The buffet had the usual fare including cereal, fruit, bread, pastries and salad fixings, along with hot items like scrambled eggs, breakfast potatoes, pancakes and more. And there was a made-to-order omelet bar as well. Of course, when the hotel finally does reopen, breakfast will look a lot different from the buffet experience I had in very-early 2020.

I decided to skip my go-to breakfast -- a veggie omelet -- and opted for some Japanese cuisine, including miso soup and fried rice, along with the delicious homemade yogurt and granola parfait.

I especially enjoyed the high ceiling and open-air design of the Grand Dining Room.

We headed to Botero Lounge, a small bar in the center of the hotel, one afternoon while my daughter caught a nap in her stroller (a parenting win, if you ask me).

After waiting nearly 10 minutes for a server to take our order, I ended up going to the bar to order a margarita on the rocks. I was served a frozen beverage, instead. I wasn't impressed with the service but the drink was strong enough to help me forget about the brain freeze.

For the hotel's upscale dining, head to Humuhumu. The menu includes Polynesian and Hawaiian cuisine, with island favorites like poke, pork belly and mahi-mahi.

We didn't eat there because prices range from $40 for a chicken dish to more than $150 for a steak, which is too lavish for my pocketbook. In fact, I heard another parent quip that keiki get a free meal and stuffed-whale toy, but given the price of the adult entrees, they felt they deserved a golden whale.

We never ate dinner at the resort at all.

I love finding local restaurants wherever I travel and a friend had recommended both Monkey Pod Kitchen, which is less than a five-minute drive from the hotel, and Coconut's Fish Cafe, located in Kihei. Both were fantastic and I highly recommend that anyone traveling to Kihei try a Monkeypod Mai Tai -- it won't disappoint.

Thanks to the $60 in annual DoorDash statement credits from my Chase Sapphire Reserve, we ordered in dinner from Coconut's Fish Cafe one night -- for free.


The grounds of the Grand Wailea are nothing if not expansive. With nine pools and Jacuzzis, a world-renowned spa with 40 treatment rooms, a huge workout facility, seven bars and restaurants and a string of shops the hotel is a destination in and of itself.

By far the biggest advantage of staying at the Grand Wailea is that you'll find yourself right on Wailea Beach -- one of the best beaches on Maui, and some might say, in the world.

This quarter-mile stretch of sand is the perfect spot to enjoy an entire day (or heck, an entire week) of beachy fun. The ocean is usually calm and you'll find good snorkeling on both ends of the beach around the rocky outcroppings.

You can rent gear like kayaks, snorkels and fins, and paddleboards from the Aqualanni stand near the beach path, but prices aren't cheap. For example, you'll pay $50 per hour for a stand-up paddleboard. By comparison, you'll pay around $100 per week from the shops in nearby Kihei.

There are also the hotel's acclaimed pools, including an adults-only pool, a pool dedicated to those taking scuba lessons and another with a shallow, sandy bottom that's perfect for babies and toddlers.

The pools are on various levels of the property but are connected by a number of waterslides, a rope bridge, artificial caves, a lazy river and the world's only water elevator.

The elevator takes you from the pool at the bottommost level to the pool at the top level, with the help of thousands of gallons of water that moves in and out of the elevator shaft each time it goes up and down.

(Photo courtesy of Hilton)

With so many pools, we didn't have an issue finding lounge chairs every morning.

Other amenities, like the Tarzan swing, were a hit with our family. If you have a little daredevil like I do, grab a lounge chair near the swing because you'll probably be spending a lot of time there.

Of course, there's the ever-popular swim-up Grotto Bar, where adults can grab a beverage and maybe catch a game or two, away from the intense sun.

Hawaii is a popular wedding destination, so it's no surprise the grounds include this stunning little chapel, surrounded by a koi pond, complete with a small waterfall.

The resort offers a long list of activities, some free; some with a fee. For example, most of the fitness classes cost $15+ per session. But you can also take advantage of the property's free on-site activities like art tours, botanical tours and hula classes. The Grand Wailea is home to one of the largest art collections in Hawaii, and includes paintings, stained glass, mosaics and large sculptures.

One morning, we participated in the "E Ala E Sunrise Experience," where guests are led in a traditional Hawaiian chant and ceremony that's meant to release life's stresses.

Guests also have access to The Rock, the incredible 20,000-square-foot kids' area that's on the ground floor of the Wailea wing of the hotel. It's equipped with everything from toys to video games.

The Lego Island corner is truly impressive.

I'd be remiss if I didn't mention the Wailea Beach Path in more detail. Although it isn't technically an amenity of the Grand Wailea, it's another great reason to stay at this property (or any of the other properties in this area of the island).

The three-mile paved path runs right along the ocean and will take you past beautiful beaches, resorts and homes. We walked it at least once a day and during a stroll one evening we were lucky enough to spot a pod of humpback whales just past the shoreline.


It's hard to summarize the service at the Grand Wailea as the property is so large that nothing feels very personalized. Everyone we dealt with was friendly and helpful, but it felt like you were being ushered along with the masses, whether you were getting your wrist band and pool towels for the day or waiting in line to be seated for the breakfast buffet.

Essentially, this isn't the place to go if you want sophisticated service.

Overall Impression

There's no doubt that the Grand Wailea is an excellent choice if you want to use Hilton points to book a vacation to Hawaii. You can maximize the value you're getting from your rewards by booking during pricey months.

Otherwise, a stay at the Grand makes you feel a bit like you're getting nickeled and dimed at every turn. The fact that the hotel doesn't offer free parking ... anywhere ... was a big turnoff for me. I don't like being forced to pay for a valet service I don't want. Plus, the resort is clearly aging, and you can tell there is a need for some long-overdue repairs.

Related: Why traveling to Hawaii is worth it

Honestly, had I paid cash for our stay I would have felt a little cheated. Again, I think it's more about managing your expectations and recognizing the positives and negatives than about the property. For example, the rooms aren't at all impressive, but the hotel's grounds sure are.

So, if you're looking for an intimate escape, steer clear. But if you'd like a fun, easy spot for a family vacation, the Grand Wailea is a great option. You certainly won't run out of things to do if you decide to spend your days on the property. And there are plenty of things to see and do off property, as well.

All photos by the author.

Featured image by (Photo by Meghan Hunter/The Points Guy)
Editorial disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airline or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.