Trip Report: The Grand Wailea With Kids

My family started summer off with a bang this year, leaving for Hawaii the day after school was out. We spent 3 nights on Kauai, followed by 5 nights on Maui, and it was glorious. (Yes, it was a great “do-over” from last time ). I’ve written a few posts about this trip already, but I wanted to write one exclusively about the Grand Wailea, as it is such a popular “aspirational” destination for many, especially those with kids.

If you are looking at a map of Maui, the Grand Wailea is here:


Rooms at the Grand Wailea are incredibly expensive, starting at around $500/night for a standard room. I booked 2 connecting Deluxe Oceanview rooms for 5 nights entirely with points, but if I had paid the rack rate, we would have plunked down a cool $8000 for our stay. (Yikes and no thank you!).

If you are interested in the details, here is how we got enough points for our stay:

  • Josh got a Hilton HHonors Surpass card with a 60,000 point sign-up bonus
  • Josh got 2 Citi Hilton Visa cards for 50,000 points each for a total of 100,000 points
  • I transferred 145,000 American Express Membership Rewards points to Virgin Atlantic when they had a 30% bonus, then I transferred the points from Virgin to Hilton at a 1:2 ratio.  This gave me 390,000 Hilton Points
  • I got a Citi Hilton Reserve card (actually, I got two using the double-browser trick, but who’s counting).  This gave me 2 free weekend nights for each card (a total of 4).

This is a total of 550,000 Hilton points, plus 4 free nights. Back in the day (as in, last year, when I originally booked this trip), this was more than enough for two rooms, five nights. Alas, because of the massive Hilton HHonors devaluation that happened earlier this year, that is no longer the case. However, most people do not need/want 2 rooms, so unless you are slightly crazed and have had sleep trauma with your children, you can definitely still plan a free vacation at this hotel using the above earning method(s).

Our rooms were large and looked exactly like this photo:

Screen shot 2013-07-08 at 9.33.01 PM


Sorry I didn’t take actual photos, but by the time we got to the hotel, my kids were exhausted and Josh was annoyed, so I couldn’t stop everyone from running into the rooms and flopping down on the beds, dumping luggage everywhere and opening all possible drawers, doors and windows.

My favorite part of the rooms was definitely the lanais. We ate breakfast here every morning, and it was lovely.

Screen shot 2013-07-08 at 9.38.11 PM

The Lay Of The Land

The Grand Wailea is gigantic. We were there for six days and I didn’t see it all. The main attraction here is the series of connecting pools and waterslides: it’s great for kids. The beach is also very nice. (It is shared with the Four Seasons, so you know it’s gotta be good)!

I think that the resort looks kind of like a sea turtle. The most conveniently located rooms are in the Chapel and Lagoon wings.

grand wailea layout

Things To Do At The Resort

My kids are 8 and 10, so they were the perfect age for the pools, waterslides, and beach. We spent between 3-6 hours every day enjoying the water. I also used the fitness center, which was extensive. Sadly, I didn’t make it to the spa, which I hear is AMAZING. (Sorry, Emily, I wanted to compare notes on this with you, but I just didn’t get a chance to go!)

The grounds of the hotel are beautiful, and it is fun to just wander around and look at all of the landscaping. My kids also enjoyed watching the koi fish in the network of ponds. (Tip: if you ask at the restaurants, they will give you fish food and let you feed the fish!)

We definitely spent some time exploring outside of the resort (hiking and snorkeling), which I will write about soon.

Dining Options

The food here is extremely expensive. How expensive? Think of the most expensive meal you’ve ever had, then tack on another hundred dollars. Needless to say, we didn’t dine much at the resort. Here’s what we did instead:

Breakfast: we stocked up on breakfast items from Costco and ate breakfast on our lanai, which was fabulous. There is a mini fridge in each room, so it’s easy to keep basics on hand (milk, yogurt, juice, etc.).

Lunch: there are a ton of delicious spots near the hotel. The Kinaloe Grill Food Truck was incredible.

kinaole food truck

Kinaole Grill Food Truck

kinaole menu

We shared the Coconut Shrimp and the Garlic Shrimp.


Coconut Shrimp

One our way to the airport, we stopped at TJ’s Warehouse and Geste Shrimp: I can highly recommend both. We also went to Coconuts Fish Cafe, but found it to be just okay.


  • We drove 2 minutes up the hill and went to Monkeypod kitchen a couple of times. Stellar cocktails, yummy food to match.
  • Another night we made reservations for Koiso sushi – 12 seats, fantastic sushi, very bland atmosphere (located in a strip mall).
  • We did eat dinner at the resort one night and used some coupons we got at check-in for being Hilton Gold members. The coupons were good for $40 off dinner, plus 2 free drinks. Since we each had a set, we saved a ton: total cost for our meal, including drinks and dessert, was $30.

Tip: if you are planning a trip to Hawaii, you can read my tips for saving money on food when you are in a hotel in Hawaii here.

My Honest Opinion

I looked forward to this trip for over a year. I read tons of reviews and did a lot of research, and I was certain that it would be the perfect blend of action (pools, waterslides, beach) and relaxing (poolside, beach, spa) that I am always looking for. However, while I enjoyed the Grand Wailea, I don’t think I would go back.

Why? I think the main reason is that it was too big for my taste. It’s hard to understand just how big it is unless you are there. There are just so many people at the resort…everywhere…that it is a little overwhelming. Another reason is that morale seems to be low. I didn’t meet any employees who seemed to enjoy what they were doing, and I encountered a few who seemed genuinely annoyed. This definitely clouded my opinion of the property. Lastly, I was expecting more luxury, but everything seemed a little run down and kind of basic.

I am starting to embrace the fact that I really appreciate and enjoy smaller, quirkier hotels (yo Kimpton, I’m talking to you)!

However, I am really glad we went. We had a great time, especially because it was (almost) free. If you are planning a trip to the Grand Wailea, I would advise you to read as many reviews and trip reports as you can before you go. That will give you an idea of what to expect. (You can read my “Top Five Opinionated Tips For The Grand Wailea” here). All in all, this resort is great for kids, and it is beautiful.

I say, if you’ve got the Hilton points, go for it.


  1. Great review. I think you nailed it exactly. I live on Maui and have splurged a few times over the years myself at the Grand. I feel the same way that the luxury price tag does not go with the mediocre staff and frankly the restaurants as well. However the spa is spectacular and one of the nicest I ve ever been too. We bring snacks and go offsite for dining as well. Kinaole food truck is a family fave of ours as well. Aloha.

  2. Points Pixie says

    Carey – Wow, confirmation from a local is an amazing stamp of approval 🙂 Thanks.

  3. I’m really glad you posted this opinion as Husband and I had gotten all revved up about possibly going there. It’s just those darn interconnect pools that have grabbed my imagination.

    We really do need to make sure our dollars spent are worth it, don’t we?

    By the way, does anyone else know of a hotel/resort that has a great pool complex somewhat along the same lines?

  4. Great comprehensive review!

    BTW I didn’t get to comment on the contest blog because I was traveling, but here’s what I love reading about on your blog:
    – points and miles specials, like the SouthWest one you just did, or other easy ways to score miles
    – subscription box oohs and ahhs, Being far from shopping, I really love this service and learning about new great boxes
    – personal trip series of blog reviews, i.e. Hawaii, New Orleans, New York
    – contests! I love winning stuff!
    – travel tool tips, i.e uber, autoslash
    – how to get a lot of points (i’m still struggling with this one)
    – storytelling, I love to hear your travel tales!

    • I agree with Rebecca (and all the other comments on the contest blog) on what I love to read on your blog. Of course, I still need help with how to get to the minimum spends on my new card. Sigh.

      Love you blog posts. Thanks for sharing and making me (us?) smile.


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