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!

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78 responses to “Spring Break to Maui: Introduction & Planning

  1. Big respect to you guys. The grand wailea is truly an amazing property and for you to get it for free is awesome.

    What activities or sights did you see on the island?

  2. Hawaii’s on my list…. but I can’t get myself to take that long plane ride when I can hop to the Caribbean instead and be on the beach in three hours. How long does it take you to get there?

  3. Going to Hawaii myself in July/August and been stalking the car rentals for convertibles for a month through all the methods with no luck. Consistently $125+ more expensive for a week’s rental than a small car. Thinking about just paying up and booking the convertible now figuring I probably won’t save more than $25 to $50 in the end even if prices do come down. What do you think? And any reason you didn’t get a convertible for Road to Hana? I hear it’s highly recommended.

  4. Thanks for this. I am planning a trip for next March. I have two questions:
    – When exactly did you go? March? April?
    – How far ahead of time did you book your reward rooms with Hyatt and Hilton? I am still accumulating points/certificates for this trip, and am wondering if I should go ahead and do a church now or wait until late May (a full 91 days from my last churn). Thanks!

  5. Glad to hear that you two enjoyed Maui – I absolutely love it there, and visited most recently this past fall. Looking forward to hearing where you ate – I’ve got a bunch of favorites, but there’s always room for more 🙂

  6. I loved Maui. It’s so beautiful there. I went for spring break a few years ago and stayed at the Hyatt Regency also in an ocean-view room. It was definitely the right choice in Ka’anapali.

    Daraius, since you did fly directly on Alaska Airlines to Maui, it only would have cost you 25,000 British Airways miles for that first class ticket on Alaska Airlines. (vs. 37,500 on American). You did say you wanted to use your American miles so it’s probably the right redemption for you, but wanted to mention it just in case.

    @Kay: I go to the Caribbean several times a year, but Hawaii is completely different. Caribbean is more of a long weekend trip where the main appeal is sitting on the beach for a few days. Hawaii has lush vegetation, hiking, canyons, volcanos and perfect for a week-long vacation. It’s not a beach to beach comparison at all 🙂

  7. “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 got to give credit to Emily. For 7 days stay, max of 2 islands; one week per island is relaxing.

    One curious thing…I would have thought you would use Hawaiian Airlines points to get there. Does HA fly to your area? If so, why use other airlines other than HA?

  8. Hey Darius, loved your post. Thinking about going to Maui with the wife. Really anxious to read the second part of your post. When do you estimate you will be posting the activities and other recommendations.

    Also on a desperate note. On one of your older posts you had mentioned that we should limit out credit card apps to 12-16 on 24 month period. But, I was counting your app-o-rama posts and it seems that you have applied for and gotten approved for CC’s in excess of that number. Can you please explain?

    I have also noticed that chase, citi and Amex are all using the experian credit score for me, so there have been quite a few pulls.

  9. Was the resort fee waived at the Grand Wailea for both the weekend night and the points stay?

    The Alaska flight is sold as First, so BA charges a 3x premium, not 2x.

  10. Isn’t Hawaii great? I love Maui. It is probably my favorite island. I can’t wait to go back this fall. I’m glad you give up that crazy notion of waiting until you retire to go to Hawaii.

  11. Darius, I too am a huge Hawaii fan despite the long flight from Florida. We were on Maui in February and stayed at the Fairmont and the Grand Wailea and loved them both. I’m amazed you were able to find award rooms so close to your arrival date…it pays to just keep trying! Did you have to pay the $25/day resort fee?

    @ Wedding Spend-On our 12 Hawaiian vacations we have only rented a convertible one time….at that only lasted for 5 minutes. When we went to put our luggage in the trunk, it wouldn’t fit! We had read enough about car break ins so we knew we wouldn’t be comfortable leaving anything inside the convertible. I love the road to Hana and my suggestion would be to get an intermediate SUV that would give you a better view because you are further off the pavement. The other suggestions to others making the trip is try to spend at least one night in Hana. That way you can leisurely enjoy the beauty of the road to Hana, do some amazing hiking , and not feel like you are on a race to get there and back.

  12. Glad to hear you enjoyed it! My husband actually took some real convincing to go to Hawaii, but he is finally joining me there later this year and I trust that he will also fall into the camp where once you go, you want to go back. 😉

  13. @Daraius: I just verified and all Hawaiian route two-cabin planes are priced differently on BA than the domestic, Mexico and Caribbean ones. Even on American Airlines. Thank you for the update! 🙂

  14. Another tip about the road to Hana, go all the way around. The vast majority of people reach the O’heo Gulch and turn around and go back the way they came. Huge mistake. I know a lot of people do this because they believe it is a violation of their car rental contract to keep going. I don’t believe that it is true since the road does have a highway designation, but it is true that for a long stretch the road is not paved. As long there is no rain and the road isn’t washed out it is perfectly safe to drive all the way around. The contrast between the wet side (Hana) and the dry side is striking.

  15. We are staying at the Hyatt Regency in September for 7 nights using points. I have an ocean view club room booked but have debated booking the ocean suite instead. Points are not an issue. Any recommendation on which room to stay in for the seven nights? It has been a big debate around here so any opinion would be appreciated.

    • @Dyhppy – We went on the Road to Hana for a day, went on a submarine ride, went to a Luau, saw the Big Banyan tree, went snorkling etc. More to come in future posts.

      @Kay @ Travel Bug Diary blog – It is much longer to Hawaii from the East Coast than the Caribbean, but it was ~3 hours from Kansas City to San Jose and ~5 hours from San Jose To Maui.

      @Wedding Spend – You can always book a refundable reservation to lock in the price and cancel it if you find something cheaper. We didn’t get a convertible because it cost more, but still had a nice time in our Ford Focus!

      @Mark – We went in the middle of March. I booked the rooms about 2 months out, but ideally would have done it sooner. It is probably best to wait a full 91 days until the next time.

      @Food Wine and Miles – Our experience with the food was mixed – some was good and some wasn’t. But the views made up for it!

      @The Miles Professor – It was beautiful over there. We traveled in first class, so would have paid more Avios for those flights. I also want to save our Avios for when we use our Travel Together ticket.

      @Dave Op – Hawaiian Air doesn’t fly to Kansas City, so we couldn’t fly on them. They also didn’t have availability for the dates we wanted to travel.

      @Dan – It should take about a month to post the full trip report. I’m lucky that in Kansas, my credit inquiries are split almost evenly between the 3 credit bureaus, so I can apply for more cards.

      @Tim – The resort fee was waived, but the valet was not.

      @Scott – That was crazy talk on my part! We should have stayed the night in Hana and done more exploring, but there’s always a next time.

      @Diane – I didn’t find the rooms the 1st time I checked, but they showed up after a few weeks. We didn’t pay the resort fee at the Grand Wailea. I agree with you that we should have spent at least one night in Hana.

      @Mommy Points – Ha! I think he’ll like it and will want to go back.

      @Brant Jackson – I’ll post detailed reviews and pictures later on, but if there are more than 2 in the room, I’d go with the suite since it is more spacious. The oceanfront rooms in the center building have a better view, but they are smaller. But they are also more convenient to get to the lounge for breakfast/snacks. You could also stay some nights in the suite and some nights in the oceanfront room. If one partner is up later at night or earlier in the morning, the suite is better since you have a separate room and don’t have to wake the other partner up.

      On a separate note, the Hyatt Regency is a old hotel and the new Andaz in Wailea could be a good choice since it just opened!

  16. Daraius, my wife and I were also there over spring break for 9 days. This was our trip:

    Flights: I did the Icelandic Air deal last year and bought their Saga points and was planning on getting 3 coach tickets but then the deal abruptly ended and I had one day to get a booking on Alaskan Air and couldn’t get though on the phone as the Saga Club was overwhelmed with this ill-chosen deal of theirs. I finally did get through but had to book immediately with no planning and so I chose some dates at random – turned out to be Spring Break – getting 2 first class return tickets rather than 3 coach as originally planned. Cost was about $300 each.

    Lodging: We used our 2 free nights each from the Chase Hyatt cards to stay at the same Hyatt on Maui as you did. When we called Hyatt to reserve just a week before arriving we were told there was no space. But my wife called the hotel front desk directly and they found space for us but in a standard room which overlooked the parking lot where they were building a new wing and we were told it would be noisy. So she asked about an upgrade and agreed to pay about $80 a night for an ocean-facing room plus $14 per day for parking (how I hate that).

    Anyway, when we arrived, I had a bit of a disagreement with the car attendants who didn’t want to let me stop at the entrance and insisted on valet parking which I refused (I never allow it since my car was smashed by the valet parking attendant once at a W hotel in Seattle – took 6 months for them to refund me). So, when I got to the front desk I was a bit irritated and the reception clerk could tell. As soon as he saw the Platinum level on my registration he came out with the leis and free water, told me to forget about the parking fee as we could park on the far end which was better for our room access anyway as he was putting us in an ocean-facing room. So we got the nice room and when I checked out after 4 days – the bill was $0. No resort fee (I didn’t even know about this as we are not resort people and would never have guessed there was such a thing), no parking fee, no upgrade fee.

    You may think we got a real deal but Hyatt is not so dumb as we now want to stay more at Hyatts! When I returned from the trip I found an offer from Chase for a free Hyatt night if I spent $3000 in 3 months – I did that in 3 weeks and we’re already thinking of our next trip.

    For the rest of the Maui trip we stayed in Hana for 2 nights at the State park in a cabin – rustic at best, very cold at night but the views of the ocean crashing on the rocks during the exceptionally rough tide were amazing. Plus we hiked up the Seven Sacred Pools path in the National Park up there.

    The last 3 nights we spent in a bungalow in Paia which was a very different town. Can’t wait to get back to Maui.

  17. love your blog-
    Great to here you finally made it to maui. We spend four to six weeks there every fall, at time share in westin villas kaanapali. Feels like home.
    Curious to hear where you dined.
    We took that sub trip in September and love it!

  18. I went to Maui for Spring Break too in April! Just missed you there. I’m also in the middle of writing my trip report. We stayed the 1st night at Courtyard Marriott Maui Airport for 20K points, and 3 nights at a Maui Eldorado Condos in Kannapali for $550 (included car rental). Parking was $8 a night. In my opinion, Hyatt Regency is too expensive cost and points wise. We also did the Road to Hana, which was awesome. Of course we ate cheap, but the cheap local food is better than touristy food :).

  19. Maui no ka oi! So glad you got to experience South Maui – most bloggers just stay at the Hyatt but I think Wailea is so much nicer. I myself prefer renting a condo in Kihei (you can get an oceanview condo at Kamaole Sands for $89/night, with a full kitchen), then stocking up on groceries at Costco and getting poke at the Foodland deli.

    Re. the road to Hana, we like doing it in reverse (note, single lane, fast-driving locals, and scary-ish cliffs part of the way) – going to Kula and then going east. By the time we hit Hana and have lunch, most tourists are just getting there, so we get to experience the road from Hana back to Kahului pretty much all by ourselves.

    Looking forward to your trip reports. And booking another trip to Maui. After all, it’s been almost three months since I went. 🙂

  20. I do agree the road to Hana is one of the highlights of the island. The black sand beach and red sand beach along the way are amazing. Like nothing you’ve seen before.

    For road to Hana, I did it in one day and didn’t stop for a night along the way. I don’t regret that decision. When I went, I got up at 7 am and was probably back around 3-4 pm in the early afternoon. We didn’t rush or anything and had plenty of time for walks and pictures and hanging out at the beaches along the way and even stopping for lunch. We also hiked to the seven sacred pools and took a swim.

  21. When you stayed for one night in Hyatt each in Santa Clara and Los Angeles, did the hotel have a shuttle to/from the airport, or how did you get to/from the hotel?

  22. Hi D and E,

    Great trip report…as always it’s inspirational to your readers!

    I had to write to thank you once again. My husband and I just returned from Orlando. We flew first class on United using miles (75,000 miles per person round trip at a value of $4,000) and we even got to experience the new lay flat seats which were amazing. We also got to utilize the United Club thanks to our 2 free certificates per year (we each have our own United Mileage Plus card so we get 4 per year). We stayed at the Hyatt Regency Grand Cypress, which is a category 4, for 4 nights. I booked using my two free night certificates from the Chase Hyatt Visa sign up bonus plus 22,000 Ultimate Rewards points for the remaining nights (Regency Club 44,000 total). Not only were the resort fees and taxes waived because we used awards, but the hotel moved us to a higher floor (18th pool view with views of Epcot and nightly fireworks show), honored our late check out for being a Platinum level member, and comped the $50 per person Regency Club fees for the nights we booked using the free night certificates…which they did not have to do, but much appreciated.

    At time of booking the Regency Club King rooms with pool view were going for $513 per night including taxes, resort fees, etc. The flight round trip was going for $4,000. The United Club passes retail at $50 per person, per one-day pass. Our vacation retailed at $6, 252, but cost us 150,000 United miles, $60 in airline fees, two Hyatt free night certificates, 44,000 Ultimate Rewards points transfered to Hyatt at a 1:1 ratio and 4 free United Club passes. Grand Total of $60 out of pocket for a $6,000 trip (retail cost).

    It’s all thanks to you two for all of your hard work and all of the time you take to help everyone here travel the world, in style, for very small money. Thank you, thank you, thank you! Looking forward the the rest of your trip report!

  23. Thanks! That is exactly what I want to do during the Christmas break. Still trying to figure out if my gf and I should spend either Christmas or New Year day in Maui. Hope I can find good flight deals for miles in that period.

  24. @Wedding Spend: Use a local car rental place (not the national chains you book online). The most fun vehicle to drive in Maui is a soft top Jeep Wrangler. They’re very common at the local places, and cheaper.

    If do the Road to Hana the right way (ie. not turn around when you get to Hana, but continue on the road and up the volcano), you’ll need an off-road capable vehicle. The road is unpaved for 18 miles or something like that. It’s alot of fun and the road gets scary, narrow, and very high elevations.

    I don’t condone drinking & driving, but taking a bottle of rum, buying a coconut from a roadside vendor (filling it with rum), and tearing it up in a 10yr old Wrangler is a great way to spend 6 hours.

  25. D- Hawaii is awesome isn’t it? I visited about 4 years ago and did Oahu and visited Maui for a day. I recommend to anyone going to Hawaii to take in a few islands if you have the chance. The road to Hana was amazing, I took a tour so I didn’t have to drive the road all by myself. It was certainly a bumpy ride but a memorable experience all the same. Did you check out any of the beaches with ‘black sand’?

  26. Hey I saw that you paid only like $2.5 in fees for your Hawii trip. I recently booked at trip to the Dominican Republic using my AA mile rewards. It cost around $100 per ticket in fees or taxes. Is this normal? There are 4 of us going so these fees came to around $400! ;/

  27. did you include the annual fees on the cards whose bonuses earned you the points and miles?

  28. D, how do you get so much vacation, bro? I thought you just spent 3 weeks in India.

  29. Just wondering why you didn’t use Avios points from San Jose to maui it would have only be 25000 points. Unless of course there was no availability since u booked kind of late. I am going in two weeks using Avios points.

  30. @Lyndie: Hawaii is a domestic destination while Dominican Republic is international. When you travel internationally, you have to pay airport, immigration and departure taxes. For Dominican Republic, the airport fees are about $35 each way and then departure and immigration taxes of $30 are assessed on the way back. So the $100 you paid for each ticket is normal.

  31. I have the Hilton Reserve card and plan to put those 2 free weekend nights to good use. Can that offer be churned or repeated , like the regular Citi Hilton card? Have you or Emily do it?

    • @romsdeals – Renting a condo could be a better deal in Maui.

      @KateFromCA – Thanks for talking with me about Hawaii at the LA FTU! Wailea is much more peaceful than around the Hyatt and a condo could be a better value. And we’ll certainly try the road to Hana from the opposite direction next time.

      @Adam – They had a free shuttle to and from the airport.

      @corinne – Thanks for reading and for sharing your success. Those are my favorite type of comments!

      @Tig – Why not both?

      @texasguy77 – It sure was fun. We did check out the black sand beaches and I’ll post pictures in future episodes.

      @emily – I did not, but good reminder to add another ~$200.

      – We’re lucky that Emily gets 3.5 weeks paid vacation and can take 1 week unpaid. We were in India for ~2 weeks last year.

      @Jane – I wanted to save avios points to use with our Travel Together ticket.

      – We were able to get 2 Reserve cards at the same time, but am unsure of the current status since “Citi” recently changed the rules.

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  33. Daraius and Emily! Good for you and thanks for breaking everything down in miles/points and how much you spent–or didn’t! A two year+ newbie with this awesome finding of gathering and using points to the fullest, let alone a sleep-deprived mom, needs all the specificity and details possible! Hats off to both to both of you!

  34. Thanks for this post. My wife and I are planning the same type of trip, but going to Kauai instead. Although, I showed her this post and she’s now asking me if we can split the 6 night itinerary between Kauai and Maui. 🙂

    We went to Kauai and Maui last year. We now want to go every year with points. We wish we knew about points accumulation two years ago when we were paying for our wedding. The points would have paid for the honeymoon.

    Definitely rent a Jeep while there, but only rent it for the days you really need it. A compact car will suffice for days you’re not planning on sight seeing. Next time we take the road to Hana we are taking a Jeep. To reach the best points you need the height and 4×4.

  35. @Dyhppy- I agree—the Grand Wailea was beautiful! We went on the Road to Hana, on a submarine tour, to the spa, went snorkeling, laid on the beach, etc. We’ll have two posts dedicated to all of the activities we did, so more to come later!

    @ Kay @ Travel Bug Diary blog- I think Hawaii was totally worth the flight! There’s so much more to do than the beaches and that’s what I liked best about Hawaii versus other beach destinations.

    @ Mark- The whale watching season runs through march-April, and we saw many whales when we were there, and did not even go on a tour. Many of them came up near the beach at the resorts!

    @ Food Wine and Miles- The food was good—but one of my favorite restaurants is still Villa Mahana in Bora Bora.

    @ Dave Op- Thanks! I agree that one island per week is more relaxing. It was a wonderful trip!

    @ Mommy Points- Yay! I am so glad you convinced your husband to go along. I’m sure he will enjoy it. Hawaii is a place where there is something for everyone!

    @ Scott- Thanks! We didn’t try that but will do it next time. It sounds like the 4×4 may come in handy for that drive.

    @ Brant Jackson- You can’t go wrong in either room. We enjoyed the suite because it had more space, but both are very nice rooms!

    @Frank- Staying in Hana was a great idea. If we had more time, we would have stayed one night there and driven to the airport from the cabin.

    @Karen Cagle- We dined at a mixture of places—from local Hawaiian eateries to the hotel restaurants. We will be posting our detailed reviews soon! I agree the sub trip was so much fun!! 🙂

  36. Pingback: Hyatt Regency Maui Suite | Million Mile Secrets

  37. Pingback: Hyatt Regency Maui | Million Mile Secrets

  38. Darius,

    Could you explain how do you get the diamond suite upgrade certificate and specifically will it work in conjuction with the 2 free weekend nights certificate recieved from the Chase Hyatt card

    • @Monte – You get 4 Diamond suite upgrade certificates only when you re-qualify for Diamond elite status each year. They are valid only on paid rooms, so you can’t use them with the free weekend nights.

  39. My husband and I just returned from a wedding anniversary Hawaiian getaway. The entire trip, except for rental car, was on points/miles, with the Iceland Air-AS opportunity tossed in just for fun. We were on vacation from 31Mar to 17Apr and visited the San Francisco Bay area outbound and returning as we originate in FL and wanted stopovers in SFO. DL Skymiles from TPA-OAK. Used points for Holiday Inns in OAK. We flew AS, in FC, from OAK-OGG and checked in for two nights at the Grand Wailea Marriott, then scooted to the Hyatt Regency for two more. Flew HA, on pts, from OGG-KOA and checked in to the Marriott Waikoloa using a free night certificate. Next, bounced over to the Hilton Waikoloa Village for eight nights using back to back AXON bookings. We had the best time on both islands and ticked off the list of usuals: snorkeling, volcanoes, luaus, good eats, beach lounging, people watching, shopping, cruising, etc. It was necessary to island hop back to OGG from KOA to hook up with AS for the flight to the mainland, but that was really the only slight inconvenience of the entire trip and we can blame no availability out of KOA for that. We booked everything about 6-7 months before our departure and certainly are thankful for the opportunities these miles/points programs avail us. Elite status w/Marriott, Hilton, Priority Club, Hyatt guaranteed lovely rooms w/breathtaking views, and we are still pinching ourselves that we were able to have so special of a trip for very little “work.” We are in our 60’s, and encourage anyone who is reticent to get in on these forms of travel strategies, to take the plunge. The world awaits, and Darius and Emily will help you!

  40. Pingback: Eating around the Hyatt Regency Maui | Million Mile Secrets

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  45. Hi D:
    Can you please provide some assistance? I’m trying to book a couple of nights at the Grand Wailea on a stopover to Honolulu and cannot find absolutely ANY openings not only in the month I’m trying to go (September 2013) but all the way through May 2014, then I just gave up. Am I doing something wrong, or is it that booked already?

  46. How did you manage for parking in Maui, did you have to pay for it. Any advice on how to avoid paying high parking foee in Hawaii

  47. Pingback: Eating Around the Grand Wailea | Million Mile Secrets

  48. Pingback: The Road to Hana | Million Mile Secrets

  49. Mark Schneider

    Great post on your trip to Maui. I love hearing tips on how to maximize points. My partner and I did a 7 nighter to Kauai in December, using free Hyatt nights at the Grand Hyatt (with diamond status free breakfast & apps in the club lounge) and Marriott points at the Courtyard Coconut Beach (stunning location!). We used United points from Colorado Springs via LAX to Lihue. We enjoy walking, so we nixed renting a car and used the local bus — great way to meet locals and it was pretty efficient (note, you can only take on one carry-on bag on the bus) to and from airport.

    We loved Maui, doing a 10 day trip back in 2005 — I loved the narrow road around the northwest side of Maui! For the overall vibe, we like Molokai best, camping and B&Bs, it’s the most Hawaiian (per capita) and local of the islands. We happened to visit during the annual Maki-hiki ceremony & games, being introduced to an incredible band called Kupa-aina.

    I’m kind of tempted to visit Oahu because it’s ‘got it all’ and the contrast between the rampant tourism of Honolulu vs the Hawaiian sovereignty movement is stark. But for overall, if I could go back to any island, it would be Maui.

  50. What is the difference between Chase Ultimate Rewards points compared to Citi Thank You Points? What credit cards are used ?

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  59. Pingback: Winter Getaway to Kauai: Part 1 - Using Miles and Points to Get to Kauai | Million Mile Secrets

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  69. Pingback: Winter Getaway to Kauai: Part 13 – Conclusion and Blog Giveaway | Million Mile Secrets

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  73. So, how long and how much did it “cost” you to accumulate: 75,000 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?
    You can get 30,000 from American’s credit card, 30,000 on United ‘s credit card, and 50,000 on Southwest credit card, and 100,000 on Hilton/AmExp as bonuses for “free,” but how did you gain the rest? You would have to travel at full cost and/or charge several thousands of dollars to make up the rest.
    I’m just getting started and it seems (almost) impossible for me to do this. Could you walk me through how you got all these points? Thanks.