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Behind Our Upcoming Trip to Hawaii

Now that I am back from Cuba, it is time to head home for 1 day before my family and I take off for our vacation to Maui. This is the final leg of a hectic travel schedule the past few weeks, since I decided to squeeze Panama and Cuba in between the Chicago Seminars and Hawaii. The final leg should be more relaxing though.

I have written about bits and pieces of this trip before, but I think a good overview post that shows the various points/miles strategies I used could be useful.

Trip Planning

hawaii award travel
Kakalele Blowhole Maui.

When my son was younger we had a lot more flexibility of dates, however that isn’t quite the case anymore now that he is in High School. For that reason I am always looking to combine holidays and local staff development days to plan a trip. Nevada Day (the anniversary of the state joining the Union) falls at the end up October and ends up giving kids 3 days of school off. This means that taking a week in Hawaii only causes him to miss 2 days of school. That is tough in High School, but doable.

Flying to Hawaii

One of the best options to Hawaii from the West Coast is British Airways Avios. Those have been my go-to in the past, but this time I decided to do things a little differently. Last year I received Alaska MVP Gold status through a match and have several upgrades I need to use before the end of the year. Since fares were quite cheap to get to Hawaii, I used ThankYou points for my wife and son’s tickets and paid cash for mine. All three were upgraded to First Class for free.

Since our flight on Alaska is from Oakland to Maui, we must first make it up there. Thankfully we have lots of Southwest points and will re-position using our companion passes. The total cost in Southwest points is 6,300 for our entire family of four.

Total Cost: 32,932 ThankYou points + $168

Flying Home from Hawaii

While I still have a couple of upgrades, the timing of the flights back from Hawaii on Alaska didn’t work for us. Thankfully American had availability to Los Angeles on one of their shiny new 32B planes. They charge 17,500 miles, but British Airways only charges 12,500 Avios on the same flight. (Since this is a domestic flight, we don’t need to pay anything extra for a lap child. A mistake I made!)

There was no AA space from LAX-LAS, so I used Southwest points once again to get us from LAX-LAS. (3,502 points total.) The 32B is a nice plane and perhaps the best coach experience you will get to/from Hawaii.

Total Cost: 38,750 Avios + 3,502 Southwest Points + $33.60

Hotels in Maui

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Grand Wailea

The first four hotel nights were rather easy. Earlier this year I applied for the Hyatt credit card when they were offering a 20% rebate on award bookings for cardholders. When booking this trip I decided to use the sign-up bonus of two nights at the Andaz Maui at Wailea. It can be tough to get a room there but since we are traveling during the shoulder season, it was quite easy.

Next, we decided to use the two free weekend nights from the Citi HHonors Reserve card at the Grand Wailea next door. The two properties are very close to each other and we loved our stay at the Grand Wailea last time. Can you say water elevator? The pools really are amazing!

Our flight back to the mainland is a redeye on the 6th day, so we only needed one more night, which I haven’t booked yet. Prices this time of year are relatively reasonable, making award redemptions a generally bad value. I do think we will ultimately stay at the Hyatt Regency in Kaanapali since I really like that property, however we have the flexibility to play it by ear.


hawaii award travel
A secluded spot we found during a drive on Maui’s west side.

As of now we have absolutely no activities planned. Even though baby Elizabeth’s first big trip was to Mexico City last month, we have not taken a vacation together as a family and wanted to leave things open. Additionally, my dad is in Maui for the first 3 days of our trip, so we will be spending time with him. I do want to drive the road to Hana this time, but I’m not sure the baby will like so much car time. We will see.

Overall Savings

Unlike with the last trip I don’t have the exact dollar figures to give you for the rooms and flights at the time I booked, but I have minimums. The cheapest roundtrip flight to Maui was slightly more than $450 and the rooms cost more than $400 each for our nights. Just taking that into account the total value is around $3,000, however we still have that 5th night as well and we are flying in first class on the way there. No matter how you slight it, the value is tremendous.


This is the 4th trip to Hawaii using point & miles that I have taken in the past 2 1/2 years. In the Summer of 2013 my wife and I did a very similar Maui trip and later that year we made a last minute winter holiday trip to Honolulu with our son. Earlier this year we also made a “last vacation before the baby” trip at the last minute to Kauai. Good stuff.

The point of this post is not to brag about all of our trips to Hawaii, but instead to show you different strategies that I use to get there. If Hawaii is indeed your dream destination it can be expensive, but miles & points can definitely help. Many of the articles linked to within this post detail the various strategies we have used on all four of our trips if you are interested in learning more.

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  1. Got the Alaska status match recently, but I guess I’m pretty dumb because I had no idea it came with immediate upgrades. I’ve held AA gold before, and that does not have free upgrades unless you earn them later, so my expectations were low I guess. AA gold is basically worth a checked bag and not much more. How do the upgrades work on Alaska?

  2. Shawn i just read your linked article about status match. Is it possible to match southwest companion pass to alitalia to get skyteam elite + to use on delta international award ticket?

    • CJ, my understanding is that if you match SW CP to Alaska MVP Gold, you’ll be eligible for upgrades on Delta, since AS and DL are still partners and DL upgrades on award flights. You’d basically just be behind Delta elites in the line.

    • I went through the ThankYou search engine and booked. Since I have the Prestige card each point was worth 1.33 cents each for the flights. Flights to Hawaii were cheap, so it work out to be less than using miles plus since the airline sees it as a revenue ticket we earn miles and most importantly I could apply the upgrades.


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