Spring Break to Maui: Introduction & Planning

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Over Spring Break in March, Emily and I visited Maui in Hawaii.  This was our first time to Hawaii so we were very excited!  We spent only $570 dollars for a trip which has a retail cost of $8,731 for some Big Travel with Small Money!

Of course we wouldn’t pay the retail price ourselves, which is why we collect miles and points.

Can't Wait to Go Back!
Can’t Wait to Go Back!
Trip Report Index:

I always thought that I’d “save” Hawaii for when I retire because it would be relatively easy to visit and explore later in life.  But one of the most common reader questions is “How do I get to Hawaii?

And almost everyone who has visited Hawaii wants to go back (if that isn’t a ringing endorsement, what is?) so we decided to go!  As luck would have it, I fell sick the first 2 or 3 days, but still had a wonderful time.

Emily:  Thanks to all the readers for nudging Daraius to plan a trip to Hawaii.  I can’t wait to go back!  We loved going on the scenic Road to Hana, exploring the ocean in a submarine ride, and enjoying the clean beaches.  Oh, and Daraius locked us out of the rental in our first 30 minutes on Maui!
On the Road to Hana
On the Road to Hana
Daraius:  I booked the flights 2 months out, which often isn’t the best time to find award seats.  The best times are usually right when the booking schedule opens ~11 months out or in the few days before departure (if flights aren’t sold out).

But Emily wanted to travel over Spring Break since lots of folks would be on vacation at her work and she wouldn’t be missed as much.

In this post, I’ll explain how Emily and I visited Maui using miles & points.  We stayed at the Hyatt Regency in Maui for 4 nights using cash & Hyatt hotel points and the Grand Wailea (a Waldorf-Astoria hotel) for 3 nights using Hilton points and the free weekend night from the Citi Hilton HHonors Reserve card.

Later, I’ll post a more detailed account of the different airline, hotel, food, transport, and activity options so you can plan a trip to Maui as well!

Keep in mind that the chart below covers only the cost for hotels,airfare & car rental and not for dining, activities and other travel expenses.

 Retail CostOur Cash CostMiles & Points UsedSource of Miles & Points
2 one-way tickets from San Jose to Maui on Alaska Air~$700 per person ($1,400 total)$2.50 per person ($5 total) in taxes and fees37,500 American Airlines miles per person (75,000 miles total)- Citi American Airlines Personal & Business Cards

- Bank Direct Checking Account
2 one-way ticket from Kansas City to San Jose on Southwest~$230 per person ($460 total)$2.50 per person ($5 total) in taxes and fees14,160 Southwest points total- Chase Southwest Cards

- Southwest Companion Pass
2 one-way tickets from Maui to Los Angeles on United~$1,000 per person ($2,000 total)$2.50 per person ($5 total) in taxes and fees40,000 United miles per person (80,000 miles total)- United Credit Card

- Chase Ultimate Rewards points transferred to United
2 one-way ticket from Los Angeles to Kansas City on Southwest~$200 total ($400 total)$2.50 per person ($5 total) in taxes and fees11,981 Southwest points total- Chase Southwest Cards

- Southwest Companion Pass
7 Days Car Rental in Maui$207020,700 Thank You Points- Various Citi Thank You Cards

1 Night at the Hyatt House in Santa Clara$118 (or 8,000 Hyatt Points)$1180
1 Night at the Hyatt Place in Los Angeles$116 (or 12,000 Hyatt Points)$1160
1 Night in an Ocean Suite at the Hyatt Regency, Maui$730$3260Hyatt Diamond Suite Upgrade Certificate
1 Night in an Ocean Suite at the Hyatt Regency, Maui$700$027,000 Hyatt Points per night- Various Chase Ultimate Rewards Cards

- Points Earned from Staying at Hyatt Hotels
2 Nights in an Oceanfront room at the Hyatt Regency in Maui$550 per night ($1,100 total)$027,000 Hyatt Points per night (54,000 Points total)- Various Chase Ultimate Rewards Cards

- Points Earned from Staying at Hyatt Hotels
2 Nights at the Grand Wailea$500 per night ($1,000 total)$080,000 Hilton Points per night (160,000 Points Total)- Various Hilton Cards
1 Night at the Grand Wailea$500 per night$01 Free Weekend Certificate- Free Weekend Night from Citi Hilton Reserve
Total$8,731$57075,000 American Airlines Miles + 80,000 United Miles + 26,141 Southwest Points + 20,700 Thank You Points + 81,000 Hyatt Points + 160,000 Hilton Points + 1 Free Night Certificate


I wanted to visit 2 to 3 different islands in the 7 days we had, but Emily would have none of that, so we stayed all 7 days in Maui.  I did manage to convince her to change hotels, though!

Ideally I wouldn’t have had to use my Southwest Companion Pass and would have flown directly to and from Kansas City.  But there were no flights to and from Kansas City over spring break, so we had to use our Southwest Companion Pass to fly to and from the departure cities.

This wasn’t ideal, but it was much better than not traveling to Maui.  Emily may not have gotten a week off work if it wasn’t over spring break, so we had to find a way to make this work!

If I had to do this again, I would also consider booking the flights in economy to save money, since the flights to Hawaii were only ~5 hours long from San Diego and the seat wasn’t *that* comfortable to justify the increased amount of miles.  After all, we’ll soon be in Hawaii!

We used Hyatt, Chase Ultimate Rewards, Hilton, Southwest & Citi Thank You points in addition to American Airlines and United miles.  So it does help to have miles and points across different programs so that you have more options when it comes time to plan a trip!


1-Way Using American Airlines Miles

I couldn’t find any flights over spring break which left from Kansas City to Maui over spring break.

I usually like booking tickets as soon as the award booking window opens up (about 11 months before), but I slacked off and booked these tickets in January 2013 (about 2 months away).


So I booked a flight on Alaska Air from San Jose to Maui using American Airlines miles on Saturday morning.  Alaska Air is a partner of American Airlines which means that you can use American Airlines miles to fly on Alaska Air flights.  You will pay the same amount of American Airlines miles regardless of whether you fly on Alaska Air or American Airlines.  And you pay the same amount of miles if you fly to Maui from Kansas City or San Jose.

I paid 37,500 miles per-person +$2.5 in fees for a first class seat on Alaska Airlines, and I was able to do this online at AA.com. The retail cost of these flights was $700 per person.

1-Way Using United Miles

I actually wanted to save my United miles and use my American Airlines miles for the trip.  I have a lot of American Airlines miles and will have more with the US Air merger, but don’t have as many United miles.  But I couldn’t find 2 seats back using American Airlines miles.

But I did find 2 seats on a United flight from Maui to Los Angeles for 40,000 miles & $2.5 per-person in first class.  The retail cost of these tickets was $1,000 per person.

Southwest Companion Pass

I have the Southwest Companion Pass which lets Emily travel with me for free (up to $10 in security fees) on either a paid ticket or a ticket booked with miles.

I booked a one-way flight from Kansas City to San Jose for Friday evening using Southwest points and added Emily as my companion.  This cost 14,160 Southwest points and $5 in taxes and fees for both of us.  The retail cost of these flights is $460.

Thank You Companion Pass!
Companion Pass Made it Easier

And for the return, I booked us on a non-stop flight from Los Angeles to Kansas City.  This cost 11,981 Southwest points and $5 in taxes and fees for both of us.  The retail cost for these flights was $400.


1.  Hyatt Regency – Maui.  I booked one night using the AAA rate for ~$326 a night because I wanted to use a Hyatt Diamond suite upgrade certificate.

I then booked the next 3 nights at the club level for 27,000 points (the regular rate is 22,000 points a night) hoping that the hotel wouldn’t move us from the suite.  I figured that they would be more likely to do that if I had booked the remaining 3 nights in a club room for 5,000 more points per night.  Though if I *really* wanted to stay in the suite, I should have just paid 33,000 and booked a suite.

But I slacked off and contacted the hotel 3 days before arrival (sorry Emily!) and they could only guarantee the suite for the 1st 2 nights.

View From the Ocean Suite
View From the Ocean Suite

The Ocean Suite sells for ~$700 per night.  Since I paid the cash AAA discounted rate of $326 for the 1st night, I also had to pay the $25 resort fee which was waived for the other nights on points.

But this turned out to be great, because we were moved to a full-ocean facing Oceanfront room for our last 2 nights which had a MUCH better view than our suite!

Better View from the Full-Ocean View Room
Better View from the Club Oceanfront View Room
2.  Grand Wailea – Maui.  I booked 1 weekend night using the free weekend night certificate from the Hilton Reserve card, another 2 nights using 80,000 Hilton points per night.  Each room was selling for ~$500 on the hotel website.

I booked each night separately so that I could use the free weekend night certificate for the weekend and because I couldn’t find availability when I first started checking.  But after a few weeks I was able to book the other 2 standard nights for 80,000 Hilton points each.

Note that Hilton now charges from 70,000 points to 95,000 points for a standard room at the Grand Wailea.

Unfortunately, we also had to pay $30 per day for the valet parking and there is no other option to park nearby.

7 Pools at the Grand Wailea!

The hotel was sold out and we didn’t get an upgrade or an ocean facing room.  But it didn’t really matter since we were out of the hotel most of the time!

3.  Hyatt Place & Hyatt House

On our way to Maui, we had to stay in San Jose for the night to catch our flight to Maui on Alaska Air the next morning.  So I booked us at the Hyatt House by the airport.

On the way back, we had to stay the night in Los Angeles for the night to catch our flight back to Kansas City the next morning, so I booked us at the Hyatt Place by the airport.

The Hyatt House/Place were~$30 more expensive than a non-Hyatt hotel, but I wanted a Hyatt stay credit to get to Hyatt Diamond status again.

Car Rental

The cheapest car rental in Maui was using either the Chase Ultimate Rewards or Citi Thank You portal for ~$207.

I value Chase Ultimate Rewards points more than I value Citi Thank You Points, so I used 20,700 Citi Thank You points for the rental.

Bottom Line

We had a wonderful time in Maui and can’t wait to go back.  In an ideal world, we wouldn’t have had to spend extra Southwest points to get to and from San Jose and Los Angeles.  But it was much cheaper with the Companion Pass.

More importantly, we were able to use our miles and points to have a wonderful trip filled with lots of Big Travel with Small Money to Hawaii!

Editorial Note: We're the Million Mile Secrets team. And we're proud of our content, opinions and analysis, and of our reader's comments. These haven’t been reviewed, approved or endorsed by any of the airlines, hotels, or credit card issuers which we often write about. And that’s just how we like it! :)

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