We’re just a few days away from a family getaway to Maui, and the best part of it all is that our total out-of-pocket cost so far for flights and hotels has been less than $300- for 5 people! Oh how I love points and miles!

The Flights

Back in March, Dad and I visited Australia, and just days before our trip, we decided to make some changes to our itinerary so that we could meet some friends in Tokyo for a few days on our way back to New York.

Since Tokyo – New York was considered an “off peak award” with American Airlines at that time, our return flight from Haneda was only 25,000 AAdvantage miles a piece (and ~$44 in taxes), and we were even able to get a free one way out of it for a later date because American Airlines allows one free domestic stopover on International award redemptions. We chose Maui as our free oneway. In the end, our ticket looked like this: HND-JFK (stopover), then we’d “continue on” to Maui approximately 7 months later.

Keep in mind that Citi AAdvantage credit card holders also get 10% of their redeemed miles back, knocking this Tokyo-NY-Maui ticket to just 22,500 miles.

Now that Dad and I had tickets squared away, it was time to book the same award tickets for Mr. Points Traveler, Mom, and my brother Anthony. Anthony is currently living in South Carolina, so it was most practical to have him depart directly from Columbia (CAE). He will be meeting us in Dallas and then continuing on to Maui on the same flight segments we are already booked on. The award ticket prices for Mr. Points Traveler, Mom, and Anthony were 17,500 AAdvantage miles a piece (+ 10% of the miles back from the credit card).

A few months ago, Mommy Points blogged that American Airlines was having a discounted award ticket redemption price of 15,000 miles each way for travel between September 11 – December 17, 2013. I was naturally tempted to rebook using the lower rate, but unfortunately that would require a complete redeposit (plus redeposit fee) to save 2,500 miles each. Of course, the fee would be waived for AAdvantage Executive Platinums (which I am not).

For the return flights, we were able to book 5 tickets on the same itinerary from OGG to EWR for 20,000 United miles each. Since I have top-tier elite status with United, I was able to book everyone in an E+ seat, and we have the option for free flight changes and redeposits if we decide to extend our stay for a day or two.


Since we are arriving in Maui fairly late at night after what will be a long, exhausting day traveling in coach (thank goodness for Gogo), we are spending our first night at the Courtyard Maui Kahului Airport (category 5) by using our Marriott free night certificates that we earned from previous “stay 2, get 1″ MegaBonus promotions. This hotel has a convenient and free airport shuttle, so we don’t have to worry about renting a car late at night.

For the next 3 nights, we transferred Ultimate Rewards points to Hyatt GoldPassport (22,000 points a night), to stay at the brand new Andaz Maui at Wailea hotel that just opened up a few months ago. I luckily won 22,000 GoldPassport points at FTU in Tampa, and I was also targeted for several “bonus points” promotions over the last couple of months just for being a Hyatt Visa card member. I believe I earned 13,000 bonus Hyatt points just by meeting spending thresholds on the card, so I don’t feel as guilty for transferring too many valuable Ultimate Rewards points into hotel nights.

Mom and Dad used two free night certificates for their room from the Hyatt Visa, as well as 22,000 Ultimate Rewards points for the 3rd night. A standard room is going for around $400 a night during the times we will be visiting, so it was refreshing that as a family, we were able to save ~$2400 in hotel costs!

After booking the rooms, we applied for a Hyatt Diamond trail so that we’d be able to enjoy daily hot breakfast each day at the Andaz, among other perks such as bonus points, welcome amenities, and possible upgrades. The Hyatt Diamond trial grants you Diamond status for 60 days, and there is an option to keep the status until February of 2015 by completing 12 stays in that 60-day time period (ambitious, I know).


We’re still ironing out the details of the rental car as I continue to see the best available deal possible. If anyone has any suggestions, or if you know of any intriguing car-rental promotions, please feel free to share!


This will be the first time in Maui for all of us, so if you have further recommendations for local food options, activities, and “must-dos”, feel free to let us know. As of now we are considering the following:

  • Feast of Lele Luau – Considered the best on the island, but it’s also pricey at $115 a head.
  • Warren & Annabelle’s Magic Comedy Dinner Show – Heard some good reviews, could be a fun night out.
  • The Road To Hana – Hearing mixed reviews; is it worth it?
  • Hiking/Snorkeling – Would like to spend a good portion of the trip staying active – any recommendations would be appreciated!


  • Flights from EWR to OGG for Dad and I: Free Oneway on American Airlines
  • Flights for Mom, Anthony, and Mr. Points Traveler to OGG: 15,750 each (17,500 + 10% back on Citi AAdvantage Card)
  • 2 Rooms at the Courtyard Maui Kahului Airport for 1 Night: Free using free night certificates from Marriott’s MegaBonus promotion
  • 3 Nights at the Andaz Maui at Wailea for Mr. Points Traveler and I: 66,000 Hyatt GoldPassport points
  • 3 Nights at the Andaz Maui at Wailea for Mom, Dad, and Anthony: 2 Hyatt Free Night Certificates and 22,000 Hyatt GoldPassport points

If anyone has any recommendations for our Maui trip, please do share – we especially like “local” experiences and food!


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  • Jamison (@jamucsb) said,

    No extra persons charge for 5 people in 1 room?

  • helixcardinal said,

    Warren and Annabelle’s is awesome. One of my favorite activities after three trips to Maui. I like the highway to Hana too, but may be difficult pregnant.

  • Ryan K (Aloha Miles) said,

    Go on a snorkel/whale watch trip to lanai or molokini with pacific whale foundation. Kill two birds with one stone and money goes to whale research.

  • Ryan K (Aloha Miles) said,

    Also Freds on taco Tuesday is great! Its in Kihei across from kam-3 beach.

  • Food Wine and Miles said,

    Sounds like an awesome trip, I love Maui!

    Here are a couple suggestions, based on my last trip there…

    Road to Hana? YES, definitely – http://first2board.com/foodwineandmiles/2013/04/14/is-the-road-to-hana-worth-it/

    Hiking / Snorkeling / Other outdoor activities? Here are some of my favorites from that last trip (the kayak-snorkel combo was especially cool) – http://first2board.com/foodwineandmiles/2013/03/20/four-fun-maui-activities/

    Food? Tons of great places to eat! http://first2board.com/foodwineandmiles/2012/12/09/five-memorable-maui-meals/

  • Food Wine and Miles said,

    Forgot to mention: if you’re looking for a luau alternative, I really enjoyed the Old Lahaina Luau. It’s not much cheaper, and it’s probably not the most convenient from Wailea, but I thought it was great! http://www.oldlahainaluau.com/

  • Angelina said,

    @Jamison: We have 2 rooms at both the Courtyard and Andaz so we will be split – 2 in one room, 3 in another.

    @helixcardinal: Thanks! Definitely going to book the show now

    @Ryan K: Thanks for both! Will definitely check them out.

    @Food, Wine, Miles: Jason, thanks so much for your suggestions – reading through your posts now!!

  • June said,

    Make sure you stop for at least one breakfast at Kihei Caffe – S. Kihei Rd across from Kalama Beach. Best banana pancakes and cinnamon rolls on the island!!

  • Erndog said,

    I booked the same trip not long ago, will be there next week . . . staying at the Courtyard, too, the first night as I get in late on my arrival day.

    If your travelling over 10+ hours a day each way going to/from Maui, why not stay another day and rebook at least one room at the Wailea rate? Four nights for +/- $800 + the $75 credit? If Hyatt points are worth at least $.02, wouldn’t that make more sense + you get another day on the island?

    Also, with a group your size a car rental makes sense, but the hotel charges $30/day for valet and there is no other alternative for parking at the hotel that I can find . . . so I guess they get you on that one.

  • Dino said,

    Hi, angelina!
    AA actually allows a “backtrack” that far on that free one-way?

  • Marilynn said,

    Try this for the rental car:

  • AC said,

    How can you book Tokyo-NYC-Maui as free one way? I tried to book Tokyo-LAX-Maui and the agent told me it’s back tracking and not allowed???

  • Karenc said,

    Yes yes, the magic show is great! Road to Hana is beautiful but remember it’s about the journey! not the destination , as there is really nothing to do but turn around..or you can keep going , the road is fine.
    Best restaurant is Mamas Fish House, but there are so many great places to dine. Check out Betty’s in Lahaina…get a window seat and you are directly next to the luau, without having to pay the big ticket price. Feast at Lele is right in front of you..starts about 6:30. Betty’s has lobster specials on Wednesday nights.

  • David said,

    Hey Angelina,
    Longggg time no talk! Been in S America over a year now and you are pregnant!! Time flies!

    The magic/comedy show is WELL worth it! Laughed hard and the magic wasn’t lame!

    Road to Hana is a no brainer if you guys like waterfalls, sweeping cliff views, swimming holes, black beaches, windy crazy drives, hiking, and adventure! The road ends at the Haleakala National park and there’s a GREAT 4 mile round trip hike in it to Waimiku Falls, 400 some feet. tallest falls on the island and you hike through a bamboo forest and pass plenty of falls along the way! Very unique scenery.

    Fred’s tacos like someone said above was great! Being from NYC I’m sure you’ve been to the Melting Pot, but they have one if not. Fun and delicious/expensive fondue experience.

    For about $70 there’s a tour that drives you to the top of the volcano – beautiful views….then you get on your provided downhill Mtn bike and bike down at your own pace!!!! Can spend the whole day and stop for pictures, lunch, whatever, or just race!! Haha. Enjoy!
    - David (from Travel and Credit & the band)

  • The Miles Professor said,

    First, to everyone who asked about backtracking, AA is not concerned with your route. You just have to not exceed the maximum permitted mileage between Tokyo and Maui by more than 25% when you travel. If going through NYC or anywhere else and creating a stopover is under that, then it’s no problem. Your overseas carrier also has to publish a fare between your origin and destination.

    Glad Jason at Food, Wine and Miles already added his suggestions :) I liked his post on that.

    Alina, one of my friends, put together what she liked in Maui most:


  • The Miles Professor said,

    Oh, forgot to mention, also wanted to comment on the luau. I went to Old Lahaina Luau, which is slightly cheaper. The main difference is that Feast of Lele has private tables with table service and Old Lahaina Luau has a buffet with shared tables of 8, I believe. Old Lahaina Luau is authentic Hawaiian whereas Feast of Lele is a Polynesian mix of performance. The dancers at Old Lahaina were amazing and I can definitely recommend it!

  • Karenc said,

    Umm. Sorry, but above post by David has incorrect info re:”The road ends at the Haleakala National park”…. No where near!
    Also, just my opinion, but I don’t think they would even Allow a pregnant person to bike down the volcano…i am on Maui 4 weeks every year and there are always reports of terrible biker accidents…

  • Doug said,

    So glad I came across this post and will be extremely helpful in the future. I just signed up for the Hyatt Visa and Southwest card (and my wife the Hyatt Visa) to get a free trip to NYC for our anniversary. This will be our first trip using credit card sign up bonuses. Our next goal after this one will be a trip to Hawaii for 8 days! This will happen sometime in 2014 so hopefully we’ll be able to get the needed points and miles needed for free flights and hotels. Looking at a 4 night stay in Fairmont Kea Lani (4 free nights with Fairmont Visa) and 4 nights in the Andaz Maui (sign up for Chase Sapphire Preferred). I hate it’s all Chase cards, but I feel like we can move some credit lines around if needed. Glad to know someone made an essentially free trip for 5 happen to Hawaii! Makes me even for hopeful for my trip for 2!

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