The great, good, weird, and apologetic about the Grand Wailea, a Waldorf Astoria Resort

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What a week! I bring you alohas (that means “hello”) from Maui, the second largest island in the state of Hawaii (or as the locals call it, “the aloha state”). As a reminder, I organized this trip as a belated honeymoon taking advantage of a few interlocking opportunities:

  • Hilton Honors offers the fifth night free on award stays to all elite members (everyone, in other words), which is naturally most valuable on stays of exactly 5 nights at top-tier 95,000-point properties;

  • the new American Express Hilton Honors Aspire card offers a $250 statement credit for charges made at “participating Hilton Resorts;”

  • there’s also currently an Amex Offer for a $70 statement credit when you spend $350 at Waldorf Astoria Hotels & Resorts in the US, Amsterdam, Berlin, Edinburgh, and Paris and Conrad Hotels & Resorts in the US;

  • and the Bank of America Alaska Airlines companion ticket can be used to book moderately complex multi-city itineraries with a stopover, so we were able to use it to fly from my partner’s family in Indiana, to my family in Oregon, onward to Maui, and back to the East Coast, all for the price of a single Alaska Airlines ticket, plus taxes and fees.

There are a few ways the deal could have been stretched a little further. For example, I booked all five nights from my Hilton Honors account, including this weekend, while it would have been technically optimal to book a 5-night stay ending on a Friday night, then use the Aspire card’s free weekend night certificate to book a free 6th night and my Ascend free weekend night certificate for a 7th night, but that would have required my partner to take a lot more time off work, and we’ve already been traveling since before Christmas. As a rule I try to avoid organizing my travel around stunts unless I think I’m going to get a particularly good blog post out of them, and the free weekend night certificates will certainly get used, hopefully at a good redemption value.

The Grand Wailea breakfast mystery, solved

When I first wrote about this trip, I explained that I’d been told the Diamond breakfast benefit was “a daily $15.00 per day up to 2 person a in room dining credit. Unfortunately the $15.00 in Only for in Room dining” [sic]. But I’m now happy to be able to share the actual letter describing the benefit I was handed when checking in last Wednesday:

Breakfast, revealed!

Now, a civilian might think this letter is as clear as day: a $30 per day credit for food and beverage. But if you’re a travel hacker, you know this raises just as many questions as it answers. What’s a “day?” We arrived on Wednesday afternoon and departed on Monday; do we get six $30 credits, one per “day,” or five $30 credits, one per night of our stay? Is the credit “use it or lose it,” so we have to spend $30 per day, or can we splurge on one day?

I asked all these questions to our check-in clerk, and was told, “I don’t know, it doesn’t matter, we’ll just take $150 off your bill when you check-out.” And sure enough, when we checked out yesterday the front desk agent was happy to remove $150 from our room charges (although I did have to remind her, possibly due to the chaos the night before — see below).

The property is spectacular, but starting to show its age

Before arriving, I requested a quiet room, and we were given a ground floor king room in the “Chapel Wing,” with a balcony overlooking one of the resort’s many koi ponds. The room was indeed quiet, except for in the mornings when housekeeping carts rattled by on the tiles outside and the sprinkler system turned on to water the gardens. The room had a small refrigerator instead of a minibar, which was great for storing food, leftovers and drinks, which we found very convenient.

While everything in the room was great, it was the first place we started to notice wear and tear on the property, which opened in 1991 and underwent a major renovation as recently as 2017. At some point the door handles were replaced with longer, curved handles (possibly as an ADA compliance measure?), but the raised decorative designs on the doors were not taken into account. That means our door handle didn't have a full range of motion, and the bolt didn't fully withdraw when we turned the handle from the inside. Nine times out of ten, this doesn’t matter and the door closes anyway. The tenth time, the bolt catches against the doorframe and the door stays open. We noticed this happen one time and pulled the door shut on our way out, but the second time it took a a security guard to notice it, who promptly scared the daylights out of us when he walked into the room to make sure we were ok! Other than that, we mostly noticed small things like missing tiles in the swimming pools and chipped paint on the waterslides, but nothing that interfered with our fun.

Speaking of fun, the main attraction at the resort is its network of swimming pools and hot tubs, most of which are connected by waterslides, so you can start at the top level and slide down from one level to the next, or take one long fast ride all the way to the bottom. I don’t know why some people don’t like resorts with kids, but if you’re one of them, you are not going to like this place. There is one "adults-only” pool, but it’s right in the middle of all the other pools so there are still kids walking through all the time to get between the waterslides and the guest rooms. I guess they’re just not allowed to actually get into the water. Compare that to the Hyatt Zilara, where it was someone’s full-time job to keep kids from stepping over a rope onto the “adults-only” portion of the beach.

The adults-only Hibiscus Pool

Paying for (and eating) the food

I had my partner sign up for an Aspire card before this trip, so we had a $250 American Express credit (remember: this is a cardmember year, not calendar year, benefit) to spend in addition to the $150 food and beverage credit. Plus, since she had the $70 off $350 offer on her card, if we spent a total of exactly $500 we’d end up owing just $30 after the $150 property credit, $250 Aspire resort credit, and $70 Amex Offer credit.

Based on our experience at the Hyatt Zilara Rose Hall in Jamaica (an all-inclusive resort, so we didn’t actually spend any money there), I assumed we’d be spending a lot more than that, so I planned to charge any amount over $350 to my own Hilton Honors Ascend American Express to trigger another $70 credit. That ended up not being the case, for two main reasons: the food at the Grand Wailea isn’t very good, so we didn’t eat very much of it, and the Grand Wailea isn’t nearly as isolated as the Zilara.

In fact, there’s a shopping mall with a pair of grocery stores (same company, but with slightly different selections) just next door, so we were able to stock up on drinks, snacks, and even things like salads and sandwiches there and pay perfectly reasonable prices. Many of the prices didn’t even seem inflated compared to prices on the mainland, and Hawaii has a state sales tax that’s less than half what we pay at home.

Ultimately, when we woke up Monday morning, we still had over $50 left to spend to get up to $500 total, but we went for a morning swim and managed to run up a bill poolside to cover the difference.

Before I go any further, let me be clear that it’s perfectly possible to spend as much as I had expected to at the Grand Wailea. Importantly, we didn’t take advantage of the four luxurious options on the property: the fine dining Humuhumunukunukuapua’a, the Sunday brunch at the Grand Dining Room Maui, the Luau, or the “sunset cabana dining” option. We also didn’t order room service, which has both a $7 delivery charge and a 20% service charge. If you do any combination of those things, you’ll have no trouble triggering as many statement credits or minimum spend requirements as you please; entrees at “Humuhumu” are between $34 and $95, and sunset cabana reservations cost between $685 and $2,235 per couple (which at least is inclusive of taxes and tip). I don’t have anything to say one way or the other about whether you should try one or all of those options, I can only say I didn’t save $8,000 on my stay in order to spend it on food and drink; I saved $8,000 on my stay because I don’t have $8,000.

With that out of the way, we did eat at three on-site restaurants:

  • Café Kula. This was our go-to for breakfast, and we also ordered one lunch and a couple dinners there, all of which were basically a mixed bag. The "avocado toast” was guacamole on stale bread and the “kale burger” was a vegetarian burger patty on a bed of raw kale leaves. On the flip side, the "Wailea burger” was the best thing I had at the resort (I ordered it again our last night just because I was tired of being disappointed), and the “wild mushroom pizza” was very weird but not in a bad way at all, and if we return I’d happily try out some of their other pizzas.

  • Bistro Molokini. We had our only sit-down dinner of the trip here, and my partner thought her tofu dish was pretty good, but the real stars were the sides of asparagus and mashed potatoes we ordered. My “Hamakua Springs Bibb Lettuce” salad was a disaster, first because they gave me the identically named salad off the regular menu instead of the vegetarian menu, which wasn’t a problem, except the chef also forgot to put avocado on it, which was literally the only ingredient costing more than $0.50 in the whole $20 dish. When I pointed this out to our server she first tried to tell me that “sometimes the chef cuts the avocado so small people don’t know it’s there," but finally had to concede that there was obviously no avocado on my salad and took it off our bill.

  • Hibiscus Pool. Our final morning we ordered some onion rings off the adults-only Hibiscus Pool menu, and not only were the onion rings pretty good, once I’d taken a look at the menu I decided it might be the best “restaurant" at the resort! On the flip side, one day at the pool I overheard a waitress enthusiastically apologizing to another guest because his burger had tomato on it, which he had asked to be left off.

And that’s the vibe I got from virtually all our interactions with staff during our stay: enthusiastically apologetic. The security guard was apologetic our door was broken, the maintenance guy was apologetic our door was broken, our waitress was apologetic my salad was broken, the bartender was apologetic my cup was broken, the morning of our departure the housekeeper was apologetic for barging in on us (the one time I almost lost my temper pointing out the privacy sign on the door to her), and everyone worked hard to try to make things right.

And of course everyone was apologetic on our last night when a nearby transformer exploded and wiped out power to the entire area, with the convenient exception of the Grand Wailea’s Chapel Wing, where we were staying. When we walked up to the lobby bar for a nightcap we discovered folks were making the most of it, and the hotel was accommodating everyone with some portable emergency lighting equipment, seen here:

Desperate times = desperate measures

A note on transportation

I bounced around several times when deciding on what to do for transportation on the island. My preliminary plan was to rent a car for our entire stay at the airport and pay for parking at the hotel. Ultimately things ended up a lot simpler than that:

  • I paid $49.50 for a “shared” SpeediShuttle reservation for two from the Kahalui airport to the resort (although we were the only passengers);

  • On Friday, we paid about $34 each way to take a Lyft to and from Wailuku for the Friday Town Party;

  • On Sunday I paid $150.20 to rent a Jeep for the day from the Enterprise rental car desk at the Grand Wailea to drive up to Haleakala National Park;

  • Finally, on Monday I paid $38.13 for an Uber back to the airport.

There are two tricky things to note here. First, Lyft and Uber can drop off at the airport, but can’t pick up passengers there, so you slightly overpay for a shuttle to the Grand Wailea compared to the ride back.

Second, as convenient as it is to be able to pick up a rental car directly at the hotel, be careful when making an Enterprise reservation. The desk opens at 7:30 am, so I made a reservation for 7:30 am each morning we were there, assuming we’d only end up using one or two of the reservations. On Saturday we stopped by the desk around 9:30 am and were told they’d given our car away (which I was expecting) and that they’d have to give us a different vehicle (which I was expecting) and that they’d have to charge us $60 for the upgrade to a Jeep (which shocked me). I turned down the offer, went back to the room and changed my Sunday reservation to 9:30 am (for the same price).

Sunday morning we went by the desk at 9:30 and not only did they still have the car we reserved, but offered to upgrade us to a Jeep for $20, which I gladly accepted. I know rental agencies famously operate on slim margins, and I’m not even really upset they tried to gouge me on Saturday, but my word of warning is to make your reservation for the time you actually expect to get going in the morning, instead of the time the rental desk opens, so they don’t have an opportunity to rip you off.

One fun thing about myself I learned on this trip is that I thought I hated driving, but it turns out that was just because I’d never driven a Jeep before. They’re extremely fun.

We be wrangling

Conclusion

I hope this doesn’t sound like a “negative review” or anything like that. Our room was great, the weather was perfect the entire time we were there (until it started to drizzle on our way to the airport, just in time to help the firefighters working on the blaze started by the aforementioned transformer explosion), and we got to spend hours swimming, reading and playing in the resort’s terrific waterpark. But, we also made some obvious mistakes (“kale burger”) that hopefully this post will help readers avoid if they ever decide to check out this top-tier Hilton Honors redemption for themselves.

I’m not a tour guide, but we did spend a couple days exploring outside the resort, so I’ll try to write up a few brief suggestions for other things to consider checking out if you do find yourself at the Grand Wailea anytime soon.

Just another day in paradise