Spring Break to Maui: The Grand Wailea

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Emily:  Daraius surprised me with a stay at the Grand Wailea, a Waldorf Astoria Resort.  I had never stayed in a Waldorf Astoria hotel (part of the Hilton chain), and was looking forward to our visit to see what the fuss was about!

Daraius:  The Rough Guide says that “…minimalism is a dirty word” at the Grand Wailea.   And, boy, were they correct!

The Grand Wailea

Poolside at The Grand Wailea

Trip Report Index:

The Grand Wailea

Emily:  We pulled up to the entrance, and the staff took our luggage and parked our car.  Valet parking is mandatory and expensive at $30 per day.  Daraius couldn’t find any cheaper parking by the hotel, so we paid the valet fee.  But we didn’t have to pay the $25 resort fee since we booked the hotel using points and free night certificates from the Citi Hilton Reserve card.

The Grand Wailea

Grand Wailea Entrance

The building was painted in bright white and peach.

The Grand Wailea

Peach and White Grand Wailea

As you drove up, there was a waterfall with pretty flowers.

The Grand Wailea

The Waterfall

There was a very large lobby and in the center was a bar.


Grand Wailea Resort Lobby

The hotel is very large and has several restaurants, a spa, seven pools, and more. I liked how it was not very crowded and quiet.

The Grand Wailea

Resort’s Interior

The open lobby and bar made the hotel look even larger.

The Grand Wailea

Open Lobby and Bar

There was even a painted ceiling in the bar and lots of sculpture, graphics, murals and artifacts everywhere.

The Grand Wailea

Artwork and Bar

We took a few pictures and then walked around the hotel.

The Grand Wailea

Picture Time!

There was an ornate bar.

The Grand Wailea

The Botero Bar

I loved how well-kept everything was.

The Grand Wailea

Beautiful Garden

There was a sculpture of Three Male Hula dancers.

The Grand Wailea

Daraius in Front of Three Male Hula Dancers

The hotel was as beautiful outside.

The Grand Wailea

Outside View

There were lots of palm trees and paths.

The Grand Wailea

Palm Trees and Marble Paths

I loved the little white canopies.  They were so pretty!

The Grand Wailea

White Canopies

There’s also a reflecting pool which is a great place to take a picture.

The Grand Wailea

Reflecting Pool


The Grand Wailea

The Reflecting Pool

To the right of the reflecting pool is a small chapel.

The Grand Wailea

Small Chapel

We went inside to see the stained glass.

The Grand Wailea

Chapel’s Front View

The chapel was open so we peaked inside.

The Grand Wailea

Stained Glass Interiors

Outside were the Nai’aKauhulu (Gathering of Dolphins) sculpture.

The Grand Wailea

Dancing Dolphins

The beach is also right by the hotel, providing an excellent view of the Pacific Ocean.

The Grand Wailea

By The Beach

There were lots of lounge chairs to enjoy the view.

The Grand Wailea

Lounge Chairs

The pool area, Wailea Canyon, includes everything from slides, jungle pools with a rope swing, waterfalls, caves, a sand beach, Jacuzzis, a swim-up bar, and a water elevator.

The pools are some of the best I have seen at a resort!  There are nine pools on six different levels.  The pools are connected by a river that carries swimmers along whitewater rapids and gentle currents.

The Grand Wailea

One of the Many Pools

The connecting river made the pools seems like one giant pool.

The Grand Wailea

River Connecting the Pools

There was an adults-only pool…

The Grand Wailea

Adults-only Pool

…a kids’ play area pool…

The Grand Wailea

Kids’ Play Area Pool

…a scuba dive training pool…

The Grand Wailea

Scuba Dive Training Pool

…a volleyball pool…

The Grand Wailea

Volleyball Pool

…a pool with a water elevator…

The Grand Wailea

Water Elevator

…a pool with a waterfall…

The Grand Wailea

Pool with Waterfall

…a kids’ pool with sand, to imitate a beach…

The Grand Wailea

Sand Beach Kiddie Pool

…a general pool…

The Grand Wailea

General Pool

There were more pools than we had time to try!

The Grand Wailea

A Pool a Day Keeps Daraius Happy

…a snake pool…

The Grand Wailea

Snake Pool

…pools with waterslides…

The Grand Wailea


…a pool with a bar…

The Grand Wailea

Pool with Bar

The Grand Wailea

Grotto Bar

..more snake pools and passageways…

The Grand Wailea

Snake Pools and Passageway

…and a bar/restaurant.

The Grand Wailea

Resort’s Bar and Restaurant

There was even a koi pond.

The Grand Wailea

Koi Pond

There was a concrete pathway which connected the Grand Wailea to the other hotels and condos in the area.

The Grand Wailea


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33 responses to “Spring Break to Maui: The Grand Wailea

  1. Love the pictures.

  2. Wow those pictures are great..What a lovely property..have been to hawaii 3 times but now go east –usually france.. but this makes me re-think that….they should give u more points for showing off their property….

  3. Wow, that’s a lot of pools. I do like a swim up bar, though. I assume people get married at that cute little chapel.

  4. Lovely! Are you going to do a post soon about the spa? I’m going in a month and was wondering if it was worth it? Thanks!

  5. I am taking my kids there this 4th July. I can’t wait! The resort will be packed though. I wonder how the pools here compared to those at Grand Mayan Nuevo Vallarta.

  6. We stayed last Jan at the fairmont down the path abit, with the chase fairmont free nights. We also thought this hotel looked awesome! Were you able to get free breakfast? I don’t think golds get free breakfast normally at the Waldorf hotels??
    Thanks for all you do. I always recommend your blog to my friends.

  7. Hi everyone- Glad to hear you like the trip report! The hotel was very nice and we were lucky to stay there!

    @ Lori- We will post about the spa soon. The spa was one of the best I’ve ever been to and I would highly recommend it. Get SpaFinder gift certificates for a 20% discount to help reduce the cost. Also, be sure to go at least 1 hour early to use all of the facilities before your spa treatment. I hope you like it!

  8. Sigh. About as much Hawaiian charm as a hole in the head. Big, ostentatious and dated. Good reminder not to waste any points on this property.

  9. Great shots-brought back fond memories of going here last year with mrs BothofUs2. The spa there is truly world class and a must do activity for men and women. The only thing is that the place *feels* so expensive -we felt like visitors and not guests. We felt more comfortable at the Sheraton Maui at Black Rock. But if you have the points and the certs its worth a night or two at GW.

    • @Lively – Thanks!

      @dot cahill
      – We didn’t get anything for staying there and I don’t tell hotels that I will be visiting ahead of time!

      @Lisa – The chapel is for weddings and they have a separate wedding department at the resort!

      @Lori – There will be a post on the spa in a few days.

      @Sharon – I’ve never been to the Grand Mayan so I can’t compare. But there are a lot of pools (and the sea) at the Grand Wailea!

      @Lynn – Hilton Gold elite members don’t get free breakfast and we didn’t get it either. Thanks for reading! We had breakfast at the cafe in the hotel and went out on other days.

      @BothofUs2 – It certainly did have a very different feel from the Hyatt Regency in Maui.

  10. Looks like you went at a good time. Heads up to those not familiar with the resort during hoidays, school breaks, etc. It’s NUTS. If a pool chair is important to you during these times, save the headache and book a cabanna in advance unless you enjoy racing for a chair at 7 am.

  11. Your wife got beaten by an ugly stick. I enjoy your trip blogs but why do you feel compelled to post numerous pics of that cow?

  12. David Gray, you ought to post a picture of your significant other for us to judge. I agree he overposts, but this is his blog. If you dont find her attractive, you can at least be impressed by how much HE is crazy for his wife….as any good husband should be.

  13. @David Gray – Or is it JoeW? I don’t have any issues with your personal insults. It just shows that you are unable to argue convincingly and received less than your fair share of grey matter. But such is life.

    But I DO have an issue when you use different identities to post comments on the blog. So I just added your comment under “JoeW” to the spam list. Goodbye!

  14. Daraius,

    I’m a long-time reader and a big fan. I never interact in forums because of people like David Gray above. I am consistently impressed with your personal response to every post and an even bigger fan after seeing your mature handling of an unnecessarily rude commenter. By using your travel advice I was able to fly my then-girlfriend on business class to Rome and propose at the corner suite of the Rome Cavalieri hotel this past Christmas. I hope that when you close your computer each day you take with you more stories like mine than the juvenile posts of a ‘David Gray.’


    BTW- I stayed at the Fairmont Kea Lani right next door last April–I think it gives the Grand Wailea a run for its money!

  15. @ Dan F- Thanks for sharing your proposal story! Reading it on the blog brought a huge smile to my face. Moments like those are what collecting miles and points is all about. Congratulations to you and your fiance! I hope you have fun planning the honeymoon. 🙂

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  18. I can’t believe the rudeness of David Gray. Only explanation I can come up with is that David is jealous that Emily has Daraius and he doesn’t.

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  25. Daraius I am just starting to put together a Hawaii trip for next June (what I’m not going back to Maldives!?). Looking at the Grand Wailea as still looks a reasonable HH redemption especially in June. Couple of questions. First did you use the bikes at all at GW? I have read about them but not seen them. Wanting to know if they are actually nice or not. Second is I looked through your TR and see a lot of grey skies. Did you just have bad luck with weather? Looking at weather averages seems June is a good dry time to go.

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  27. Daraius, I am very impressed by how you handled the rudeness. I totally enjoyed reading your blogs. I love looking at your pictures and think Emily is so beautiful. She even inspires me in choosing outfits to bring for my trip. Whenever I plan trip with my husband or even trip with the family, I refer to your blogs to see what you and Emily recommended! Please keep up your good work. I am a big fan. Thank you!

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