And Now a Few Notes about the Grand Wailea

We’ve moved 45 minutes down the road to the Grand Wailea, which I could tell you we did so I could sample more of the island’s resorts but I really did because I didn’t have enough points to get 2 rooms for all 7 nights in one location (damn you, Hilton devaluation!).

We reserved 2 Ocean View rooms for 3 nights using points (an absurd 109,000 points per night per room, but at this point why am I going to keep hoarding Hilton points? I figured I’d just use them, and I’m glad I did). I booked the Ocean View rather than the base level rooms (95,000 points per night) because (well, obviously) I wanted the view and I hoped that with the Gold status I have with Hilton I would be upgraded to the Deluxe Ocean View. They were kind enough to upgrade us. Here’s the view (note: I am a terrible photographer):

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So, here are the knocks you typically hear about the Grand Wailea:

1) The hotel isn’t what it used to be; it’s become rundown in its 20+ years, and what was once a top luxury property is now one notch (if not 2) below that;

2) The pools are a Disney-like circus featuring a ridiculous water elevator and a whole bunch of other kid-friendly nonsense that makes this more like an amusement park than a luxury resort;

3) It’s expensive for what you get, and the nickel-and-diming is ridiculous.

Let’s go through these…

Here’s my high-level take: The Grand Wailea is really 2 resorts, and which you experience is dictated by whether or not you are with children and where you go while you’re here.

This is a large resort (780 rooms) and it is frequently compared with the Four Seasons next door, a comparison that is simply unfair – that resort has 300 rooms. Let’s take the Four Seasons out of the equation for a moment.

If you are here with children, this is an incredible place for them. The rooms are spacious, with sizable bathrooms, separate baths and showers and toilet areas, which anyone with kids knows is very, very helpful. The pool situation is truly unbelievable for them, with something like 7 different waterslides, an in-water water-powered elevator (I don’t really know how to describe it), a rope swing, lazy river, and a whole bunch of pools, most of which are interconnected. If your child is between, let’s say, 6 and 15, I don’t know how they don’t think this is the greatest place on earth, pool-wise. They can order lunch that comes in a sand pail ($14) with a sandwich, chips, some fruit, desserts and it’ll keep them happy snack-wise all afternoon. Plus, free* pail. (*$14).

If you are here without children, this is an incredible place, provided you stay the hell away from the children. I cannot express how beautiful the location is, situated on a beautiful beach with ocean views that go on forever. The lobby is exquisite and, I’m not kidding, I actually said, “holy shit” out loud (sorry, kids!) when I walked in. As my wife said, “this is exactly what I was hoping for.”

Here’s a terrible photo of the lobby:

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There is an adult pool area that is located far enough away from the ridiculous main pools so that it is entirely possible for you to enjoy yourself and never even notice the complete mayhem happening below.

In the evening, the lobby bar is a wonderful place to have a drink, enjoy some music and, because the resort is large, you’ll be surrounded by adults.

This is the second resort- the resort for adults.

The first knock on the place – that it ain’t what it used to be – is tough to address as I wasn’t here when it used to be what it supposedly no longer is (whew!). What I can tell you is this: the rooms will probably need some sort of re-working in the next few years, but if I never mentioned the age of the rooms you would not be struck by their age. They are nicely appointed and, as noted above, nicely laid out, especially for families. This resort was built 20 years ago and guests will probably see pieces of that age (I’m looking at a spot of rust on my balcony right now). Is it so bad that it will be what you remember about the place? Not at all. But it is probably one reason why base rooms here start at $229 and not $399.

Speaking of which – the base rooms are on the ground floor and have no view. You can decide whether it’s worth coming to Hawaii and spending $229 for a room with a view of nothing on the ground floor. Those guests have a very different experience than someone who is staying up where we are on the 8th floor with the ocean views. Again, how you choose to experience this place will completely dictate your experience.

The second knock above – the one about the circus-like atmosphere – again depends on the type of vacation you’re looking for. Want your kids to run around and have an amazing time for 12 hours a day? They’ll love it. Does the very idea of having children around bother you? This is not your resort. But they really have made an effort to lay out the 40 acres so that you can create the type of vacation you want – assuming you put in the effort. And there are still nice touches they provide – when I went to get my car from the valet they put 2 cold bottles of water in the cup holders. Nice, right?

This is not a Sandals where there are no children. This is not the Four Seasons where it is a more exclusive type crowd without over-the-top amenities for children. This is not an Aman Resort where service will be the thing you remember about the experience. It is a 4 1/2-star mass market property, that offers a nearly top-notch experience FOR THE MASS MARKET.

Which leads us to knock number 3: the cost/added fees. As I said, rooms started here this week at $229, which prices this property roughly the same as the Quality Inn located in my neighborhood at 94th and Broadway in Manhattan. Which is to say: assuming you don’t care about the view, that’s one helluva value. Yes, there is a $25 resort fee (many resorts have it here). Yes, it’s $30 to valet park and there is no self-parking. Yes, everything here is priced in what my friend calls “Hawaiian Dollars”, which is to say 30% more than anything should cost ($10.50 for a pint of Miller Lite, eg).

I would say this resort (at least during non-peak weeks) is perhaps priced more like a cruise ship: not crazy expensive to get in the door, but they kinda gotcha once you’re here. Is that annoying? Sure. If I know about that going in, can I accept it? Sure.

Let’s go back to the Four Seasons for a moment: There are 3 resorts down here that many people seem to lump together – this place, the Four Seasons, and the Fairmont. I don’t know much about the Fairmont, though I stayed at one on the Big Island years back and it was beautiful. People like the Fairmont here on Maui because it’s all suites. It’s not nearly as absurd as this place (pool-wise), and has a lower-key vibe. Rooms are not cheap, though, making it (I think) more akin to the Four Seasons than to here. The Four Seasons is the Four Seasons, and base rooms start at $500, and once you’re there it’s expensive (cabana for the day: $450). Whether the service and quiet and general Four Seasons-ness is worth it to you is really up to you to decide. I would say you’ll get a similar experience at the Fairmont (probably one notch less service-wise) for a similar price, though you’ll get more space. I tend to find Four Seasons to be wonderful, nearly perfect in terms of service, and oddly soul-less. It’s not really my speed – but it may be your speed. Again – whether a hotel is right for you is a personal decision.

The Grand Wailea is simply different than the Four Seasons and here’s what I think: if this hotel were located in the more mass-market area up at Kaanapali people would complain about it less, and it would probably be considered the nicest resort in that area. Instead, it’s located in the schmancier confines of Wailea and, given the kid situation, it feels if not exactly out of place, it’s certainly at a disadvantage compared to the other 2 resorts.

So I’ll sum it up this way: If you have children and feel that Kaanapali is a bit too middle-market for you, the Grand Wailea is a great option. The area is prettier than Kaanapali, there are nicer restaurants in this area, and if you were never planning to leave the compound it’s really beautiful.

If you chose Wailea over Kaanapali because you wanted a more grown-up experience and because you want a self-contained luxury experience, then you have 2 other wonderful options right down the street.


  1. I really appreciate this type of review. I struggle with this dilemma as I have a young child and need to determine if I am vacationing more for my daughter or more as a family experience. I can do a water park anywhere.

    Love the review.

  2. Jared,
    Thanks. A good review for a real family situation. How was the pool chair situation here. All reserved before 7 am?

    • The chair situation is abominable. I really don’t know how these large resorts can solve it.

  3. Kinda humorous that they’re charging 95K when the cash rate is $229, but in February when I’m going, it’s 70K when cash rates are $579 (and already sold out). Good ol’ HHonors.

  4. Thanks for these reviews about Maui. Very helpful as I’m picking where my husband and I will stay Mar 2014 right now.


  5. I appreciate this whole series of Hawaii posts…a lot! Thanks for a well-reasoned summary of Maui. In fact, I think you could go one step further, and compare the other islands…Oahu is more our preference.

    But I think a part of the issue with expectations is how Hawaii is portrayed on tv. Paradise-like…you don’t get your own island. But Modern Family did do 2 episodes at the 4 Seasons Maui that was funny.

  6. Jared,
    Can run down how much did you spend while staying there like meals etc. – the grand total so that we have an idea and compare w/ other properties.

    Also the question is also whether going all the way to Hawaii and spending mostly around the Pool area may not be some people’s idea of Hawaii vacation bec you may get similar experiences in some other land-locked resorts or in Cruise-ships etc.
    my 2 cents..

    • Hi. We went out into town for breakfast just about every day – much cheaper, and I wanted to get out of the hotel. We generally had a small lunch at the hotel, which was pretty reasonable at the Westin and less reasonable at the Grand Wailea (poolside meals at Grand Wailea for lunch are $14 for kids and $17-$20 for adults). Dinner we had out someplace and I would say prices were comparable to New York, though we did not go to the crazy expensive places (Spago, Mama’s Fish House, etc).

      We did several activities out of the resort, which I’m happy to write about if her interested. But there is a TON to do here if y don’t want to sit poolside.

  7. Good review – I’m surprised that you didn’t book the reservation before the devaluation? That’s the whole reason I took an accidental vacation to Hawaii this year. I used a weeks’ worth of timeshare points in Maui and then flew to the Big Island (thanks to BoA Hawaiian Air Visa :grin: ) and used a 6-night global award at the Hilton Waikoloa. In May, we did a 6-night stay in NYC. I think my HHonors account now has a couple hundred points. Like you, I will probably avoid accruing any more stays with Hilton if I can help it.

  8. Great reviews. I have been to four islands there on two separate trips. Always had a great time.

    Oh, one request. Try the Fairmount in Maui or Big Island on your next trip. It is one of my planned use of the free nights. :-)