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Travel To Hawaii For Free Part 3 – Where We Stayed In Maui

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Disclosure: Miles to Memories has partnered with CardRatings for our coverage of credit card products. Miles to Memories and CardRatings may receive a commission from card issuers. Opinions, reviews, analyses & recommendations are the author’s alone, and have not been reviewed, endorsed or approved by any of these entities. Links in this post may provide us with a commission.
The view from our balcony at the Hyatt Regency Maui.
The view from our balcony at the Hyatt Regency Maui.

Travel To Hawaii For Free Part 1 – Air Travel 

Travel To Hawaii For Free Part 2 – Hotel Options

Being able to theoretically do something on paper is different than actually doing it.  During Part 2 of our look at traveling to Hawaii for free, we looked at every property in Hawaii belonging to most of the major hotel chains.  Today we are going to look at exactly where Jasmine and I stayed during our trip to Maui this past June.  Hopefully by showing how completely possible and easy it is to take a trip like this, you will be inspired.  At the very least maybe I can share a pretty picture or two!

To start let me provide a little back story. I had originally tried to make our recent trip to Hawaii slightly more complicated then it turned out to be.  Jasmine was able to do a Diamond Challenge with Hyatt before signing up for their credit card. (Look for an upcoming post on this.)  While the credit card normally comes with two free nights at any Hyatt property, if you are a Diamond member, you get those two free nights in a suite.  Originally we wanted to use those suite nights at the Grand Hyatt Kauai.  Unfortunately they were booked for the dates of our visit, so we decided to save them for another day.

Jasmine outside of the penguin enclosure at the Hyatt Regency Maui
Jasmine outside of the penguin enclosure at the Hyatt Regency Maui

With Kauai out, we opted to focus on staying only in Maui.  While the original plan including Kauai called for only two nights at the Hyatt Regency Maui, we decided to expand that to four nights in order to fill the Kauai sized hole in our schedule.   The Hyatt Regency Maui is a category 6 hotel which requires 22,000 points per night.  We could have used our free suite night certificates there, but from what I had read the suites aren’t really much of a step up and it seemed like a bit of a waste.  Instead we decided to transfer points from Chase’s Ultimate Rewards program.  Hyatt is a 1:1 transfer partner of Ultimate Rewards.  Quite simply, we used 88,000 Ultimate Rewards points that were gained through bonuses on the Ink and Sapphire Preferred cards to cover our stays.  Total retail price: $1600.  Price for us: Free! (Note: I do know this isn’t the best overall redemption value for Ultimate Rewards, but this was Jasmine’s dream trip and it was worth every point!)

Now let me clarify something about the Diamond trial I mentioned before.  Since Jasmine is a Gold Hhonors member, Hyatt gave her the ability to earn comparable status with their program by awarding her “Diamond” status for 60 days. (To keep it she would have had to complete 12 paid nights during that time, which she did not.) Like I mentioned before since she was Diamond when getting the credit card, she got the free suite night certificates, but there was also another benefit.  When we visited the Hyatt Regency Maui, she was still within her Diamond trial period.  This meant that we were upgraded to the hotel’s nicest non-suite room and were also given Regency Club access for our entire stay.  The Regency Club included free breakfast, non-alcoholic drinks all day and appetizers in the evening.  Having access to the club allowed us to save even more money.  Additionally, the hotel’s $25 per night resort fee was waived because she was a Diamond member as well.  Total savings on food and resort fees: over $200!  Our only out of pocket cost for the entire stay was $14 per night for parking or a total of $56!

Sitting along Kaanapali beach near sunset.
Sitting along Kaanapali beach near sunset.

After four nights at the wonderful Hyatt Regency, it was time for us to cross the island to the Grand Wailea.  The Grand Wailea is a Waldorf Astoria property, meaning it is operated by Hilton.  Earlier in the year we were able to get the Citi Hilton Hhonors Reserve card which gives Gold Status and two free weekend nights at any Hilton property after 2,500 in spending during the first three months.  While the $95 fee is not waived the first year, this card was definitely still worth it.  For the two nights we stayed at the Grand Wailea, rooms were going for $600 per night including taxes.   Additionally, since we booked the room with free night certificates, the resort fee was waived.  Unfortunately, the mandatory $30 per night valet parking fee was unavoidable.

While Hilton Gold status usually gets you free breakfast, this benefit does not extend to the Grand Wailea.  We were given a couple of free drinks along with a 50% off coupon for the restaurant, but that was it.  Additionally, as Gold members, we were upgraded from the most basic “Garden View” room to an “Ocean View” room along the edge of the property.  The receptionist said this was her favorite room because of its secluded location.  While we did have views of the ocean and the room was nice, it was a serious trek to get anywhere on the massive property since we were at the very far end.

Reviews of both of these hotels are coming very soon, but the purpose of this post is to break down just what we did and how much it cost.

The Grand Wailea's lovely beach area.
The Grand Wailea’s lovely beach area.


Hyatt Regency Maui

  • Retail hotel room cost: $400 per night – $1600 total
  • Savings on resort fees and food – at least $200
  • Points cost – 88,000 Ultimate Rewards transferred to Hyatt Gold Passport
  • Out of pocket cost – $56 for parking

Grand Wailea

  • Retail hotel room cost: $600 per night – $1200 total
  • Savings on food, drinks and resort fees – at least $100
  • Cost – 2 free weekend night certificates
  • Out of pocket cost – $60 for parking + $95 for the credit card annual fee = $155

Total Retail Cost – $1,800 + $1,300 = $3,100

Total Out of Pocket Cost – $56 + $155 = $211

Savings: $3100 – $211 = $2889

Jasmine in front of the Kakalele Blowhole on the western side of Maui.
Jasmine in front of the Nakalele Blowhole on the western side of Maui.

Credit Cards Used:

Now lets take a look at the credit cards there were used and how they allowed us to enjoy this dream trip.

Chase Hyatt Card – Although we didn’t use the bonus from this card as originally planned, you do get two free nights at any Hyatt property after spending $1,000 during the first three months after account opening.  Additionally they give you a free night at any category 1-4 property every year on the account anniversary! (See part 2 for a list of Hyatt’s locations in Hawaii.)

Chase Ink Plus – This card comes with 50,000 bonus points after $5,000 in spending during the first three months. (Enough for more than 2 nights at the Hyatt Regency Maui.) Additionally, it is easy to earn points through spending with the Ink’s generous bonus categories that offer 2x points on gas and hotels and 5x points at office supply stores and on cellular phone, landline, internet and cable TV services.

Chase Sapphire Preferred – Currently offers 45,000 bonus points after $3,000 in spending during the first three months and adding an authorized user.  This is also a great card to earn ongoing points with since it carries an annual 7% points dividend on all purchases through the year and 2x points on travel and dining.

Citi Hilton Hhonors Reserve Card – You get two free weekend nights and Hhonors Gold status for spending $2,500 in the first three months.  Not the best card for your ongoing spend, but the $95 fee is worth it for at least the first year to get the bonus.  If you do spend $10,000 each year, they award you with 1 free weekend night at ANY property.


Your goals are going to be different than ours.  Perhaps you only want to visit one property, or maybe you want to visit three islands on your trip.  The idea behind this series of posts is to start to show you that everything is possible.  By the end you should be able to formulate how to make a free trip to Hawaii or anywhere else a reality.  As always I am here to help in any way that I can.  Comment below with any questions and look for part 4 coming soon!


Disclosure: Miles to Memories has partnered with CardRatings for our coverage of credit card products. Miles to Memories and CardRatings may receive a commission from card issuers.

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Opinions, reviews, analyses & recommendations are the author’s alone, and have not been reviewed, endorsed or approved by any of these entities.
Shawn Coomer
Shawn Coomer
Shawn Coomer earns and burns millions of miles/points per year circling the globe with his family. An expert at accumulating travel rewards, he founded Miles to Memories to help others achieve their travel goals for pennies on the dollar. Shawn also runs a million dollar reselling business, knows Vegas better than most and loves to spend his time at the 12 Disney parks across the world.

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  1. I have Diamond status too but haven’t had luck getting resort fees waived on cash plus point stays. Do you think resort fees were waived because your stay was all on points or because your diamond status?

  2. Going to Maui in a week…All 4 of us ! So excited! we have not decided if we visit other islands yet. What is the cheapest way to move between the islands? Thanks!

    • Usually the cheapest way is to just pay cash for the flights. I would use a flight comparison website such as to see what the prices are for your dates. It will search all of the airlines and give you a list of the best prices and options. If you want to use miles then AA and UA charge 5,000 miles each way and Hawaaian and Delta charge 15,000 miles roundtrip. Generally the prices are pretty low and in most cases you will find that inter-island flights aren’t the best uses of miles.

  3. I wish I had read this a couple of months ago…. we’re planning a special trip next spring….I was shooting for Hawaii, but couldn’t figure out how to get us there for cheap…. so we opted for a Puerto Rico vacation instead (anniversary trip) and now we’re getting psyched about that! I will be continuing to learn,and possibly get us there on our next trip after that…..

    • Don’t be sad. Hawaii will always be there. Puerto Rico is amazing in its own way. The people, the culture and the food are all wonderful and they have some fantastic beaches. Enjoy your trip!

  4. Hi Shawn,

    I found your site through MMS as well and noticed you’re in Vegas. Our family of 5 – my husband and I, our 4-year old, and 1-year old twins live in Vegas, love Disneyland, and would love to travel. How would you recommend meeting spending limits on all those credit card sign ups? Thanks!

    • I would love to help you learn about hitting the minimum spend. With five people traveling it can get a little tricky, but I can definitely help. Shoot me an email about which cards you are looking at and how much spend you need to hit. I will have a post up next week about Bluebird and how it works. There are definitely some options here in Vegas to hit your spending requirements with little effort and minimal cost. If I know a little more about your situation (What your travel goals are), I could probably recommend a course of action to get you there!

      It is great that you are looking to travel with the children when they are so young. There is so much to learn in this world and I know my son has benefited tremendously from all of his travels. It is a shame that most Americans don’t step foot outside of our borders. Thanks for visiting the site and I look forward to hearing more about your dream travels!

  5. Hi Shawn,
    I just found your blog thru MMS.. really enjoyed reading your family travel. Since I live in Houston, I will need a poisoning flight from Houston to Los Angeles thru Southwest or United? Thanks,

    • I am going to address that in one of the upcoming posts. I will breakdown more options for those who aren’t on the West Coast. Your basic options would be to re-position to Los Angeles or to use another carrier’s miles. British Airways Avios may not be the best deal coming from Houston. I promise I will address this in a post next week.

  6. I just found your blog through your article with million miles secrets….. love it! I like the traveling with your family angle,since it’s what I aim for…. a few years back,I realized my kids were soon going to be grown and gone…well, I started learning about points and miles,and traveling to the places I wanted to bring them to! I like this article on Hawaii, it’s one of the places I’m aiming for (someday) I’m going to keep reading….your article said you visited all the Disney parks worldwide,and that is a goal I like!

    • Thanks JM! Yeah I am a big coaster and theme park nerd, so it was definitely a “bucket list” item of mine to visit all of the Disney Parks. Since I grew up less than an hour from the original Disneyland, it has always been a special place for me. The fact that I was also able to share those experiences with my wife and son made them even more special!

      As for Hawaii, getting there is much easier than most people think. If you need any help or have any questions when you begin planning a trip to Hawaii, feel free to shoot me an email. Thanks again for visiting and commenting!


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