Three Free Nights at the Waldorf Astoria Grand Wailea

Three Free Nights at the Waldorf Astoria Grand Wailea

A a couple of weeks ago, I took my wife, daughter, and my wife’s parents on a trip to Hawaii. We spent an entire week on the island of Maui. I had been to Hawaii before as a kid, but for everyone else, it was their first time. It was an amazing family trip! What made it even more amazing is that we spent three free nights at the Waldorf Astoria Grand Wailea, one of the most luxurious resorts in all of Hawaii.

Thanks to having Hilton free weekend night certificates, a generous resort credit, and a timely promotion for earning points, the entire three night stay was almost free!

Gotta love travel hacking :).

In this post, I’ll explain what I did to earn those free nights. And I’ll talk a little bit about the resort itself and our experience.

 

The Hilton Family of Hotels

First of all, I need to provide some background information. It’s important to note that the Waldorf Astoria brand of hotels and resorts are under the Hilton family of hotels. Because of this, you can use your Hilton Honors points to redeem for stays in any Hilton property, including Waldorf Astoria. Same with free night certificates; a Free Weekend Night Reward certificate issued by Hilton can be used at any Hilton property in the world.

Hilton has quite a few aspirational properties throughout the world. Most of these high end luxury properties are Waldorf Astoria and Conrad hotels. And some of these retail for more than $1000!

So, to get the best bang-for-your-buck, it makes the most sense to redeem these free night certificates in the most expensive, high end property you can.

Three years ago, I had redeemed my Free Weekend Night Reward certificates for a wonderful stay at the Conrad Koh Samui in Thailand. It was (and still is) one of the most luxurious resorts I’ve ever stayed in. We had our own private villa with a large private infinity pool overlooking the water. It was awesome!

Would I spend more than $800 for such luxury? No. Probably not. But would I redeem a free night certificate at the Conrad Koh Samui? Of course!

Even though the Waldorf Astoria Grand Wailea wasn’t quite at the same level of luxury, it was an amazing stay nevertheless. Especially for a family!

 

Why I Love Hilton

While staying at a chain hotel isn’t always my first choice, it’s often necessary to get outsized value.

Of course I like to change it up every now and then. There are many occasions in which I would rather stay at a charming boutique hotel, a quaint bed and breakfast, or a local apartment in the heart of the city. The apartment rental we stayed at during our trip to Paris and Rome is a prime example. You just feel more like a local and get a better taste of the destination this way.

The problem is that you can’t do a lot of travel hacking with these independently run hotels. Sure, you can pay for these hotels with a credit card that earns bonus points on hotel stays (like the Chase Sapphire Reserve for example) then redeem Chase Ultimate Rewards points for future travel. Or you can buy Hotel.com gift cards when they go on sale. But that’s pretty much it.

Staying at ultra high end hotels for cheap (many times almost free) generally involves travel hacking the chain hotels and their loyalty programs. These chain hotels include popular brands like Hilton, IHG, Marriott, and Hyatt.

Of the above chain hotels, Hilton tops my list.

Hilton is my favorite because:

• Earning elite status is easy — Just having the American Express Hilton Aspire card, you get elite Hilton Honors Diamond status for free
• Elite status comes with valuable perks such as free breakfast and waived resort fees — This was vital for keeping our costs low at the resort
• Hilton has a decent international footprint — You can usually find a Hilton hotel anywhere you would travel
• American Express offers multiple Hilton branded credit cards — I have three of them (Aspire, Surpass, and the Hilton Honors business card)
• It’s easy to earn and redeem points and free night certificates — Sign up bonuses are usually very generous
• Hilton often offers valuable promotions on stays — For this stay, I took advantage of the current Hilton Honors Power Up promotion to earn triple times the points that I normally would earn!

 

How I Earned Three Hilton Free Night Certificates

Simply put, I earned the three free night certificates by opening and using the three American Express Hilton credit cards I listed above.

Last year, around January 2019, I signed up for the Amex Hilton Aspire card. This is an ultra “premium” card that has a high annual fee of $450, but the card easily pays for itself if used properly. Not only does it have a huge sign up bonus of 150,000 Hilton Honors points after spending $4,000 in 3 months, it also has some awesome perks. Some of the valuable perks include: free diamond status, $250 resort credit per membership year, $250 airline incidental fee credit per calendar year, and Priority Pass access with 2 free guests.

Another huge perk is earning a weekend free night certificate upon approval and every anniversary year of renewing the card. To me, the weekend free night certificate is the most valuable perk because it is easy relatively easy to redeem these certificates at Hilton properties that retail for more than $450 a night.

Like a free night at Grand Wailea!

Since I stayed there, let’s take the Waldorf Astoria Grand Wailea, for example.

It is not uncommon to find rates of more than $800 a night. I just did a search on Booking.com and saw that many of their rooms are sold out. But they did have an available standard room on December 30 for one night. Price for that night is $895 PLUS $174.83 in taxes and fees. OUCH! Paying for one night will set you back more than $1000.

 

Okay, so just by opening the Hilton Aspire card, I earned one free weekend night certificate.

What about the other two?

Remember, I also have the American Express Hilton Surpass credit card. I opportunistically signed up for this card earlier this year during an amazing promotion that has since expired. At that time, you could earn 130,000 bonus Hilton Honors points AND a free weekend night certificate by opening the Surpass card and spending $4,000 in four months. I jumped on this deal the moment I found out about it. (Unfortunately the current offer is not as generous since now you would need to spend $15,000 on the Hilton Surpass card in a calendar year to earn a free weekend night certificate.)

So that’s how I earned the second free weekend night certificate.

The third free weekend night certificate was earned by paying my June 2019 quarterly estimated taxes using my American Express Hilton Business card. With this credit card, you can earn a free weekend night certificate by spending more than $15,000 in a calendar year. I pay well over $15,000 a quarter in federal income taxes, so it wasn’t hard for me to meet this spending threshold.

In Summary

I earned three free weekend night certificates by:

1. Opening up an Amex Hilton Aspire card in January 2019
2. Opening up an Amex Hilton Surpass card during an excellent promotion in which I earned it by spending $4,000 in four months in July 2019
3. Spending more than $15,000 Amex Hilton Business card simply by paying quarterly estimated taxes in June 2019

 

Redeeming Hilton Free Weekend Night Certificates

Once you meet the spending threshold for earning a free weekend night certificate, you should receive and email that looks like this one below.

I received this certificate after using my Amex Hilton business card to pay for quarterly estimated taxes that were due on June 17, 2019. As you can see, I received the certificate just ten days after meeting the spending threshold.

Redeeming these certificates is relatively straight forward. Just like the email says, all you have to do is call 1-800-4HONORS and provide the agent with your Reward ID. You would have to tell the agent the specific hotel and date in which you’d like to stay. And they would gladly be able to book it for you. Then when you log in to your Hilton account, you’ll see your reservation as a free night stay!

There’s a few things you would need to be aware of. Including:

• It’s a free WEEKEND night certificate, so it’s only valid for stays on Friday, Saturday, and/or Sunday night
• Certificates are valid for any Hilton property where standard redemptions are available EXCEPT all-inclusive resorts and Hilton Grand Vacation properties

 

Free Nights At Grand Wailea: Our Experience

We stayed at the Grand Wailea earlier this month from December 6 though December 9.

Upon arriving, we were greeted by friendly resort staff who dressed us with beautiful Hawaiian leis. My daughter was all smiles and my wife and her parents had this look in her eyes that probably expressed something like: “Wow, what a paradise!” Her parents had a look of wonder too.

The check in process was seamless. The front desk immediately recognized me as a valued member with Diamond status and outlined all of the benefits I would enjoy. These benefits include free breakfast at the grand dining hall, 24 hour gym access, late check out, free use of beach cruisers, access to all of the pools, complimentary session with an onsite photographer, and a waived resort fee.

The Resort

They don’t call it grand for nothing. The place is huge. In fact, the grounds are so big that the resort didn’t feel crowded at all even though it was sold out and at full capacity.f

The open-air courtyards and views from the various balconies were breathtaking.

Landscaping throughout the resort was beautiful. The flowers were so colorful and the gardens were perfectly manicured.

Various works of art are sprinkled throughout the resort. In fact, the Grand Wailea is home to the largest art collection in Hawaii. You can see art piece from Fernando Botero, Dale Chihuly, and Dale Zarrella. All of the art in the property is estimated to be worth about $40 million!

The Room

Because I have Hilton Diamond status, we were upgraded to an ocean view room. It had a very beautiful view of a lagoon as well as Wailea beach.

Overall, the room was clean, comfortable, and well appointed. It wasn’t a huge space, but it was definitely enough for our family.

The Food

I’m just going to put it out there. Food in Hawaii is expensive. That’s how it is when you’re on an isolated island smack in the middle of the Pacific Ocean. When you’re on an isolated resort, it’s even worse.

Overall, I would say that food is about 1.5 times what you might expect to pay in the U.S. mainland. Some of the more budget entrees were about $20.

Since I have Hilton Diamond status, breakfast was free every morning. That saved us quite bit of money since the breakfast buffet was something like $40 per person.

The free plated continental breakfast was good enough for us. It’s not like we eat a whole lot.

Vegan options on the property were surprisingly decent. There was a variety of fresh fruits and some of the restaurants had vegan entrees. Some of the notable offerings included a Beyond meat burger, a hummus and tofu wrap, salads, and veggie pizza.

The Beach

Being from Southern California, I know a thing or two about beaches. I have to say, the beach at the Grand Wailea was exceptional.

The sand was so powdery soft. It was really the softest sand I’ve ever felt.

There was a grassy walkway that you can walk on along the coast.

 

Free Nights at Grand Wailea: Breaking Down the Costs

While I was able to redeem three free weekend night certificates for our stay at the Grand Wailea, it wasn’t completely free.

Sure, the room was completely free. But we still had to buy food and eat.

For four people, we ended up paying $407.92 dollars for food. During our stay, we ended up paying for five total meals. Dinner on Friday, lunch and dinner on Saturday, then lunch and dinner again on Sunday. Remember, breakfast was free. Since each entree was about $20, our average meal for four costed about $80. Hence the $407.92 dollar total.

We charged it to the room. On check out, I used my Amex Hilton Aspire card to pay for the expenses. I used this card because it earns the most points out of the three Hilton cards that I have. The Aspire card earns 14x points per dollar spent at a Hilton property. Not only that, one of the perks is a $250 resort credit. And guess what, the Waldorf Astoria Grand Wailea qualifies as a resort!

It Gets Even Better

By being a Diamond elite member and using my Hilton Aspire card during the 2019 Power Up Promotion to pay for these expenses, I earned a ton of points.

Logging on to my American Express account, you can see all of the points I earned.

All in all, I earned 17,116 + 1,224 + 4,488 = 22,828 Hilton Honors points!

That’s pretty awesome. Since Hilton Honors points are generally valued at about 0.5 cents per point, I basically earned the equivalent of $114.14 worth of points.

Not too shabby!!!

Cost Summary

When you subtract the $250 resort credit and the value of the points I earned, the total cost of the three night stay for our family is $407.92 – $250 – $114.14 = $43.78

$43.78 is pretty darn good considering we could have easily spent a $1000 per night for the stay and $480 for breakfast buffet ($40 per person x 4 people x 3 days).

Getting around $3,500 of value for only $43.78 is a huge win in my book.

 

Final Thoughts

As you probably already know, my wife and I are both relatively frugal and sensibly minimalist people. We don’t live ultra luxurious lives and we don’t really buy anything, especially material things we don’t need.

But occasionally we will spend a decent amount of money on amazing and unforgettable experiences. Fortunately, travel hacking with credit card points and miles has made it possible to remain relatively frugal and experience a taste of luxury.

Just like last year, my wife and I tried to avoid buying material things for Christmas presents. Our parents and siblings are all grownups and can easily buy whatever they want and need. It’s especially easy nowadays since you can pretty much buy anything online. Not going to lie, buying gifts for adults who already have everything that need is stressful!

That’s why I think it’s more meaningful to give something much more valuable: our presence for sharing memorable experiences together.

This trip to Hawaii was our gift to my wife’s parents. We were all together and we had such a wonderful time. I gave a similar gift to my parents too; but it’ll happen some time in the future. And it’s another story for another time :).