How I’m Staying at the Waldorf Astoria in Maui, for Free.

A few weeks back I decided, “I want to go to Hawaii,” and wanting to spend as little time as possible in the cold weather, I thought going in late January would be the perfect fix. So I decided to go for 10 days, and then began the process to get there. I used Delta miles to redeem a roundtrip ticket from New York. My total cost for four legs of flights, (NY to LA to Hawaii, Hawaii to LA to NY) was $10 in taxes. The flights were otherwise in the $800-$900 range.

The other major expense, even much larger than the flight, would be the lodging. I COULD always stay at a hostel if I really wanted to just save money, or if the choice was between, “Stay in a Hostel in Hawaii or not go to Hawaii.” But I knew I didn’t have to.

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I’d rather stay at a place like this. Especially if I don’t have to pay for it.

I’m a fan of “slow travel” and not feeling the need to jump around to see everything at once. On trips like this we tend to tell ourselves, “I need to see everything since I’ll probably never come back.” I wanted to focus on two islands only, Oahu and Maui, spending between 4-6 days on each one during my 10 day total trip. I can always come back to Hawaii. And I plan to.

There are three or four super nice and reknowned hotels in Maui so I decided to check into what it would take to stay at one of them. I decided on staying a couple of nights at the Grand Wailea, a Waldorf Astoria resort right on the beach

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Unfortunately there’s a reason this is known as one of the nicest hotels around. Even the most basic room goes for $500 per night. Ouch.

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I’ve saved up quite diligently, setting a goal of saving money specifically for my year-long trip around the world, so the money itself is not the issue. The point of saving money for something is then to spend it on that something.

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Especially when the place looks like this and is well known as one of the most luxurious resorts in the country.

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With tax and resort charges, I’d be looking at a bill of just under $1,200 for the two night stay. Sure, “I have the money,” but the thought of not spending $1,200 and instead investing it or having it available to extend my travel even more, was far more appealing.

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So in this case, I decided to use my two free weekend night certificates that I received from opening the Citibank Hilton Honors Reserve card last spring. The card operates a bit differently in that instead of granting a number of bonus points when you hit the minimum spending requirement, you receive certificates good for two free weekend nights at virtually any Hilton in the world. With almost 4,000 to choose from, you’ve got quite the number of options.

Weekend nights are classified as Friday, Saturday or Sunday. If you grab this card, one point to note is that it’s only good on a “Standard Room.” In my case Sunday for example was sold out of Standard rooms and only had ocean front. So I was “forced” to use it on Friday and Saturday..

A search on Hilton ensured there was availability for the days I wanted it, and one call to Hilton reservations got me to a booking agent. Within five minutes I’d given her my reward certificate numbers, (Hilton will email them to you after you hit the minimum spend on the card) and I was all set. For the sake of their booking system, the certificates, “converted” so to speak, to Hilton Points and then the agent used my Hilton points to book the room. A few minutes later and I had my confirmation.

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With that I was all set for two night of my stay in Maui. I’d be staying at one of the most luxurious resorts in the country, in a room that would cost almost $1,200. And I was staying absolutely for free. And all it took was the forethought to open up a credit card a few months prior, and put a plan together to maximize it’s value.

The Hilton Honors Reserve is a great card if you’re looking to stay in a city that is very, very expensive. You can use it at almost any Hilton in the world, but trading it in for a room that would only cost you a couple hundred dollars isn’t the best use. Instead look to places like San Francisco, London, Paris, Tokyo, or in this cause Maui, to find hotels that are super luxurious, (and super expensive.)

When my points and miles, “hobby” can let me stay at one of the grandest hotels in the country, and save me well over $1,000, then it’s definitely a hobby worth continuing.



  1. napoleon
    August 1, 2014 / 10:44 am

    Cool, what are you doing for the other 8 nights?

    • Steve Bierfeldt
      August 1, 2014 / 11:48 am

      Stay tuned Napoleon! I don’t know I’ll be getting all 10 nights, “for free,” but I’ve got a few more posts coming.

    • Steve Bierfeldt
      August 1, 2014 / 7:08 pm

      Laura it was 55,000 for a round trip from New York. There were a few Delta options that were a bit less, but this one fit my schedule better, (one stopover each way instead of two.) Also, Delta’s definitely not the least expensive carrier from the east coast to Hawaii, (miles wise,) but for me, spending 55,000 when I have close to half a million skymiles vs. spending 30k-40k with a program I have far fewer, was the better deal I thought.

      • August 2, 2014 / 9:58 am

        I guess that’s not terrible. Saver awards are 45,000. I try to never redeem more than Saver awards. :O

        • Steve Bierfeldt
          August 2, 2014 / 12:32 pm

          Agreed! You’re spot on. I grabbed a saver award for my first class ticket back from China and wow, the feeling of redeeming half the miles for the same ticket was a great feeling.