How we travel hacked our way to Maui and saved over $10,000 along the way

When Mrs. T and I got married, we talked about how cool it would be to celebrate our 5 year wedding anniversary in Hawaii. As luck would have it, Baby T2.0 was born shortly before our 5 year wedding anniversary. At that time, we were too busy with taking care of 2 little kids, so we didn’t end up going to Hawaii. It didn’t mean we stopped talking about taking a trip to Hawaii though. Mrs. T and I still wanted to take a family vacation and visit one of the Hawaiian islands.

After redeeming my Marriott points for a 5-night stay in Osaka Marriott Miyako Hotel two and half years ago and saved over $2,000 Canadian, I thought it would be super cool to use points for our Hawaii trip.

Being a personal finance blogger, I always want to find ways to maximize my money and my travel rewards points.

After some research on Hawaii Islands, flight options, and Marriott properties, we decided to go to Maui. Many travel websites suggested the Wailea Beach Resort on Maui is a fabulous place to stay and offers the most bang for the buck for redeeming Marriott points for stays.

When I first looked at how much the Wailea Beach Resort rooms cost per night, I was shocked.

A garden view room was going for $560 USD (~$700 CAD) a night!!! Some rooms cost over $800 USD!!!

Holy moly!

I have stayed in San Jose hotels for over $500 USD per night before, but that was for business. I can never imagine forking out that much money per night for a personal trip. Wow!

The Basic Travel Details

Since Wailea Beach Resort is a category 8 Marriott hotel, each night would cost 40,000 Marriott points. We thought it would be great to stay for 7 nights, so we would need 240,000 Marriott points (you get 1 free night when redeeming for 4 nights). That means we would be able to save $3920 USD/$4,900 CAD, giving us a rate of approximately ~1.63¢ USD per Marriott point. This is a much higher value than the typical estimated value of 0.9¢ per Marriott point.

To get to Maui, we found out flying direct with Air Canada would cost $680 per person. This would mean over $2,000 for the whole family (only 3 seats since Baby T2.0 is less than 2, and will be sitting on our laps). Using Aeroplan miles, it would cost 45,000 miles per person plus taxes and fees for the Fixed Mileage Flight Rewards (we can only book non-direct flights). It would require more miles if we were to go with the Market Fare Flight Rewards (can book direct flights).

Considering we are travelling with two little kids, we would prefer to fly direct, rather than having to connect via Seattle or LA.

Thanks to work, I have been accumulating Marriott rewards points and Aeroplan miles whenever I travel for work. I happened to spend a lot of time on the road in 2017, so I accumulated a good amount of points. Years ago I used to be able to use my personal Marriott Rewards Visa to pay for my business trips to accumulate Marriott points. But in late 2016, my company issued company credit cards for a company-wide cost-saving measure. This meant I no longer could “double dip” Marriott points whenever I stay at a Marriott property. It became harder to accumulate over 240,000 Marriott points on business travels alone. I had to find another way to “earn” points.

So I started looking into travel hacking.

I started reading more about travel hacking and learning what rewards points can do. For example, you can transfer American Express points to many different frequent travel programs, like Aeroplan, Delta, and SPG.

Unfortunately for us Canadians, there are only a limited amount of travel rewards credit cards available. We don’t get as many reward credit card choices compared to our American friends.

Marriott Hotel & Air Packages

Upon further research, I found a way to maximize my Marriott points. With the Marriott points, you typically redeem them for hotel stays, but Marriott also offers Marriott hotel & air packages to allow you to use points for hotel stays and airline miles.

Air Canada (Aeroplan) happens to be one of the transfer options. Usually, Marriott points are transferred to Aeroplan miles at a 5:1 rate, so redeeming 360,000 Marriott points for 7 nights of stay at a category 8 hotel and 120,000 Aeroplan miles is an excellent deal (it would have cost 840,000 Marriott points otherwise).

Aeroplan Transfer Bonus

A few months into my planning of our Maui vacation, Aeroplan had a 35% transfer bonus promotion when points were transferred from various hotel partners including Starwood, Marriott, and IHG.

With the 35% bonus, that meant transferring 120,000 points from Marriott would give us a total of 162,000 Aeroplan points.

A very good deal!

At an estimated value of 1.5¢ per Aeroplan miles, 162,000 Aeroplan miles would equate to $2,430 CAD. The 35% bonus meant we would get an extra $630.

I knew I had to get 360,000 Marriott points fast before the promotional deadline so we can get the 7-night hotel & air package.

How To Get Marriott Points Via Credit Card Bonus Points

Here in Canada, below are some of the credit cards that offer good welcome bonus points that can be converted to Marriott points.

  • Marriott Rewards Visa – 50,000 Marriott welcome bonus points after the first transaction. No fee the first year, $120 after (This card is no longer available).
  • American Express Personal Gold – 25,000 Amex welcome bonus points after spending $1,500 in the first 3 months. No fee the first year, $150 after.
  • American Express Personal Platinum – 60,000 Amex welcome bonus points after spending $3,000 in the first 3 months. $699 annual fee with $200 annual travel credit.
  • American Express Business Platinum – 75,000 Amex welcome bonus points after spending $5,000 in the first 3 months. $399 annual fee. (Note: American Express has updated the annual fee to $499)
  • American Express SPG Personal – 20,000 SPG welcome bonus points after spending $1,500 in the first 3 months. $120 annual fee.
  • American Express SPG Business – 20,000 SPG welcome bonus points after spending $1,500 in the first 3 months. $150 annual fee.

With Amex points, we can transfer them to SPG at a 2:1 rate. We can then transfer SPG points to Marriott points at a 1:3 rate.

So, if we have 20,000 Amex points, we end up with 30,000 Marriott points (20k Amex -> 10k SPG -> 30k Marriott). If we have 25,000 SPG points, we end up with 75,000 Marriot points (25k SPG -> 75k Marriott).

In addition to the welcome bonus points, American Express offers referral points. Unfortunately, Amex no longer gives you referral points if you self-referral, but the referrals work if you refer your spouse or friends.

Image Source: Redflag Deals

The Plan

Between Mrs. T and I, we applied for the following credit cards. We also referred each other whenever possible.


  • Marriott Rewards Visa
  • American Express Personal Gold
  • American Express Business Platinum
  • American Express SPG Personal
  • American Express SPG Business

Mrs. T:

  • American Express Personal Gold
  • American Express SPG Business

In total, we spent $789 in annual fees by applying for these credit cards.

We also received a total of 463,000 Marriott points. This is more than enough for the 360,000 Marriott points we need for the 7-night hotel + air package.

At an estimated value of 0.9¢ per Marriott point, 463,000 Marriott points would equate to $4,167 USD or about $5200 CAD.

Change Of Travel Plan

In addition to the bonus points from credit cards, I also had some Marriott and Aeroplan points from all my business & personal travels. As it turned out, I had enough points to book 4 extra nights of stay at Wailea Beach Resort (160,000 Marriott points needed). This would give us 1 free night.

So rather than going to Maui for 7 nights, we decided to stay for 12 nights instead.

Who wouldn’t want to stay in paradise for extra 5 nights right?

Transaction Summary

For the 7-night hotel + air package, we needed 360,000 Marriott points.

For the 5 additional nights, we needed 160,000 Marriott points.

For flights, we ended up booking Aeroplan Market Fare for direct flights. Thanks to my Aeroplan Silver status, I got 20% off the number of miles required to redeem for Market Fare Flight Rewards. So, the Market Fare ended up costing less total Aeroplan miles than Fixed Fare.

In the end, we redeemed 520,000 Marriott points and 188,406 Aeroplan miles.

By redeeming points, we saved $10,440 CAD or $8,352.42 USD.

The dollar per point value would be approximately 1.68¢ USD per Marriott points and 1.08¢ CAD per Aeroplan miles.

According to the Points Guy, Marriott points is worth 0.9¢ per point and Aeroplan miles is 1.5¢ per mile. So we got a great value with our Marriott points, but perhaps not as good for Aeroplan miles.

Credit Card Minimum Spending Strategies

Of all the credit cards that we applied, every card except for the Marriott Rewards Visa had minimum spending requirements. Without crossing the minimum spending requirements, we wouldn’t be able to get the sign-up welcome bonus points. A thing to note is that the associated annual fees do not count toward the minimum spending requirements.

In other words, we had to spend

  • 2x American Express Personal Gold -> $3,000
  • American Express Business Platinum -> $5,000
  • 2x American Express SPG Personal -> $3,000
  • American Express SPG Business -> $1,500

Or a total of $12,500 in a span of a year and a half.

That’s a lot of money, considering we only spent $51,144.77 in 2017 (excluding business expenses).

Planned big expenses

How to meet these requirements? For that, we carried out our credit card minimum spending strategies. Basically, we timed the application of each credit card just before a planned big expense. Some big expenses included:

  • House insurance renewal
  • Car insurance renewal
  • Car maintenance
  • FinCon17 expenses
  • Airplane tickets
  • Hotel reservations
  • Car rentals

Extended health benefits

In addition to the planned big expenses, we also utilized my work’s extended health insurance. The extended health insurance covers a certain amount of health benefits per year (i.e. $500 annually for massage per person). So Mrs. T and I would each book massage sessions and use the new credit card to pay for these sessions, then get reimbursed. In 2017 my work’s extended health insurance changed coverage provider mid-year, so it allowed us to have double up on the annual extended health benefits (i.e. getting $1,000 worth of massage per person).

New purchases on the new card

Whenever we have a new card, this card becomes our default spender. This should be pretty obvious. In other words, all purchases will go on the new card until the minimum spending requirements are met.

When Travel Hacking Goes Wrong

For the most part, it was straightforward to keep track of all the expenses to make sure we meet each card’s minimum spending requirement. But I somehow mess up my tracking for my American Express Business Platinum card.

I ended up calling American Express a couple of times and begged for forgiveness. Fortunately, I was awarded the 75,000 Amex points. Phew!

Lesson learned? Track the spending carefully so you don’t lose out on the welcome sign-up bonus points.

Start Traveling Hacking Today

It is pretty cool to know that we saved over $10,000 for our Maui vacation. This is why travel hacking is so attractive. If you want to start travel hacking, you can use my referral links to get significantly more Amex welcome bonus points.

This way you get more Amex points and I get referral points. A win-win for the both of us!

Dear readers, have you travel hacked before? Any success stories? What are your favourite credit card minimum spending strategies?

You Might Also Like


  • Reply
    Mrs. Groovy
    February 19, 2018 at 8:41 am

    Power to you for pulling this off! It’s awesome! I don’t have the mental energy or the stomach for all this hacking but we’ve got to at least take some baby steps with a cash back card or something.

    • Reply
      February 19, 2018 at 12:42 pm

      Thanks Mrs. Groovy, it definitely took some planning to pull this off. But it was very worthwhile to know that we saved over $10,000. 🙂

  • Reply
    February 19, 2018 at 9:00 am

    I’m impressed you saved so much money! I was happy when we travel hacked our way into free flights for a trip to Europe. Did you find most of this information (points transfers etc) by searching the internet or reading the fine print on the points?

    • Reply
      February 19, 2018 at 12:45 pm

      I found most of the information by reading travel hacking blogs & forums. There is a ton of info on the internet.

      • Reply
        February 19, 2018 at 1:04 pm

        Nice article! Would you say your main go to place is The Points Guy website?

        • Reply
          February 19, 2018 at 4:04 pm

          That’s one of the places. There are a few Canadian focused traveling hacking sites too.

  • Reply
    February 19, 2018 at 9:10 am

    Wow. That took a great amount of work. I imagine it was well worth the effort. I am new to travel hacking. This post was very helpful.

    • Reply
      February 19, 2018 at 12:45 pm

      Thanks, glad the post was helpful. It was definitely worth the effort given we saved over $10k.

  • Reply
    February 19, 2018 at 9:52 am

    That’s a lot of cards. Nice job. I’ll start travel hacking again this summer. I did too much last year and Chase started turning down my applications. We’ll need to figure out what to charge on those cards too. That’s the hardest part for us.

    • Reply
      February 19, 2018 at 12:46 pm

      Yea I had to plan out how often we apply for credit cards to make sure none of my applications are turned down.

  • Reply
    Tom @ Dividends Diversify
    February 19, 2018 at 10:45 am

    I’m impressed with your savings. It’s just not activity I enjoy, so I guess I lose out on the savings. Tom

    • Reply
      February 19, 2018 at 12:47 pm

      Travel hacking isn’t for everyone, it’s quite a bit of work tracking expenses and all the different rules. Nothing wrong admitting it’s not for you.

  • Reply
    Mr. Tako
    February 19, 2018 at 11:41 am

    Great travel hacking story Tawcan! You saved quite a bit of money! We did a little travel hacking on our trip to Japan this fall — it takes a bit of work but it’s definitely worth it!

    You can definitely find ways to save big in Hawaii too. Check out my series of posts from our 2016 trip to the Big Island:

    • Reply
      February 19, 2018 at 12:48 pm

      Thanks Mr. Tako, I will have to check out your tips. 🙂

  • Reply
    February 19, 2018 at 1:55 pm

    Great you find so many places that accept AMEX. Here in Ottawa it’s pretty limited to a few chain grocery stores and restaurants. And not many places that you can buy pre-pay credit-cards with Amex. Lucky you!

    • Reply
      February 19, 2018 at 4:05 pm

      That’s definitely a problem in Canada as many places don’t accept Amex. We had to phone around and make sure Amex is accepted to plan out our expenses.

  • Reply
    Accidental FIRE
    February 19, 2018 at 6:02 pm

    Wow, that’s impressive Bob! I’m also super surprised American Express “forgave” you for under spending and still gave the points. That shows the power of a phone call I guess.


    • Reply
      February 20, 2018 at 2:08 pm

      Yea I was really lucky. After I found out I quickly made sure I spent some money to cross the spending threshold and called a few times to talk to the supervisor. I got lucky.

  • Reply
    Mr. Shirts
    February 20, 2018 at 4:44 am

    That’s an awesome story and you got to visit one of my favorite places on earth. One recommendation for the next time you go back to Hawaii is focus on the miles for travel rewards then find a cash / travel-credit card for an AirBNB or VRBO. There are tons of great condo options with full kitchens on most of the islands.

    • Reply
      February 20, 2018 at 2:10 pm

      Thank you, Mr. Shirts. We were looking into AirBNB or VRBO but there aren’t any rewards points you can redeem for those. There are definitely some great condo options w/full kitchens with AirBNB/VRBO.

  • Reply
    Lady Dividend
    February 20, 2018 at 5:16 am

    Wow, that’s really impressive. Even if it takes you more time to figure out a trip with points, the monetary savings are huge. This will have me thinking twice about whether free groceries are really such a good reward.

    • Reply
      February 20, 2018 at 2:11 pm

      Free groceries are good too but if you can get more value for your points, it makes sense to take advantage of that.

  • Reply
    February 20, 2018 at 6:26 am

    Great job Tawcan!!!! I use a scotiabank momentum infinite visa for all purchases (whenever possible) throughout the year and end up with $800-$1000 cash back (approx. $36k annually). We typically take one vacation each year costing roughly $5-7k, do you think it would be more advantageous for us to start using a travel card(s) instead? If so which would you recommend? Thanks Mat

    • Reply
      February 20, 2018 at 2:12 pm

      Our default go-to-card is the Capital One Aspire. But the welcome bonus points of Amex and other cards are too attractive to pass up. You should do some research and calculation to see if it makes sense to apply for a few of these rewards cards.

      • Reply
        February 22, 2018 at 8:26 pm

        Did you apply for each card every 3 months? Do you cancel the cards prior to paying the next years annual fee? How did applying for all of the cards affect your credit score. You have me very intrigued, thanks

        • Reply
          February 22, 2018 at 10:37 pm

          Some every 3 months, some not. Again we timed our application to big spendings. And yes cancel the cards prior to paying the next year’s annual fee. My credit score actually went up which I found it kinda odd.

  • Reply
    Mr. Groovy
    February 20, 2018 at 7:22 am

    Thank you, Bob. Just bookmarked this page. Mrs. Groovy and I are building a house this spring/summer, so we have a big travel-hacking opportunity before us. It would be a shame to let such a wonderful opportunity slip away. Posts like this give us the motivation and confidence necessary to see that that doesn’t happen. Cheers, my friend.

    • Reply
      February 20, 2018 at 2:13 pm

      There are a lot of expenses with building a house, definitely don’t miss this huge travel-hacking opportunity!

    • Reply
      February 23, 2018 at 11:10 am

      Thanks. So 360,000 marriot points gives you 7 night stay + 120,000 aeroplan miles? Thats seems to good to be true

      • Reply
        February 23, 2018 at 12:15 pm

        Correct, well that’s for a category 8 hotel. If you stay at a lower category hotel, then you need less points.

        You can see more info here:

        For Air Canada it’s Hotel + Air Package 1.

        • Reply
          June 5, 2018 at 9:10 pm

          What’s the easiest way to accumulate Marriott points? Can I convert my existing Aeroplan milesto Marriott points at a 1:5 ratio? Doesn’t that mean if I had 72k Aeroplan miles, I’d convert to 320k Marriott points…and that’d net me a 7 night stay PLUS 120k Aeroplan miles?!?!

          • Tawcan
            June 8, 2018 at 9:05 am

            I think you can convert Marriott points to Aeroplan miles but not the other way around. So you need to earn Marriott points first to get the Marriott travel + hotel package.

  • Reply
    February 20, 2018 at 10:43 am

    Well done

    Sad to say, the Credit Cards in the UK, don’t have anything like the same hacking opportunities..

    • Reply
      February 20, 2018 at 2:13 pm

      The choices in Canada are limited too. There are so many more rewards credit cards in US.

  • Reply
    Financial Pilgrimage
    February 20, 2018 at 8:02 pm

    I need to get onboard with travel hacking. Hawaii sounds pretty good right about now!

    • Reply
      February 22, 2018 at 9:58 am

      It’s a great way to save money for sure!

  • Reply
    February 21, 2018 at 6:59 pm

    Wow sweet Bob

    Sounds like a awesome trip. You read about travel hacking but as you mentioned its was different south of the border. Nice to hear of how it can be done here in Canada. Maybe i should consider switching up my cash back card.

    • Reply
      February 22, 2018 at 9:59 am

      If you can get more bang for your money by signing up for a few credit cards to get the extra welcome bonus points, it totally makes sense.

  • Reply
    February 22, 2018 at 3:33 am

    So glad your hacking worked!
    We have used miles for free flights to visit family and go someplace new in the US. Sometimes, it was an emergency trip, but it helped to avoid the high cost of a last minute seat.
    It’s getting tougher to gain free seats! With several discount airlines cropping up, flights have gotten cheaper so we travel to other states for a new experience. A lot of tickets are $100 for a round trip flight.

    • Reply
      February 22, 2018 at 10:02 am

      It is indeed getting harder to get free seats for flights via miles. 🙁

  • Reply
    Dividend Diplomats
    February 25, 2018 at 7:51 pm

    That is some serious travel hacking Tawcan! Hopefully it made the trip that much sweeter. Way to maximize all of your points and credit card points. I can’t wait to unload some of my Hilton points that I have been accumulating while traveling for work.


    • Reply
      February 26, 2018 at 7:31 pm

      Thanks Bert. It’s awesome to be able to use up these points that you earned while traveling for work.

  • Reply
    February 26, 2018 at 1:10 pm

    You’re speaking my language! We’ve gone or 12 or 13 trips without paying for airfare. I keep a spreadsheet to track our cards and spending. I also list our award flights and hotels and I think it’s somewhere around $70,000 of value we’ve gotten from travel hacking over the years, plus another couple million points and miles still in the bank. That said, I just went to Norway for a week and paid $99 each way, so there are good deals to be had paying cash!

    • Reply
      February 26, 2018 at 7:27 pm

      It’s always awesome to be spending very little money (or no money at all) to go traveling.

  • Reply
    March 1, 2018 at 5:45 am

    Travel hacking seems very attractive, but in reality it didn’t work for us. We ended up spending way more over the course of a year than we normally do (we’re rather frugal) and most of our basic bills are not payable via credit card without extra fees. Seeing as how we don’t ever travel for work (which seems how most get all their miles!) we never racked up enough other than the bonuses. In the end, we closed all of the cards as we started to get hit with frauds who stole our credit card information. I love that everyone touts credit card hacking for travel, but sometimes it doesn’t work out for everyone the way it does for others. Nice work on your hacking!

    • Reply
      March 1, 2018 at 5:30 pm

      That makes sense. We are lucky that many of the big expenses were payable via credit card without extra fees. So we felt we should take advantage of the opportunity.

  • Reply
    Nicolas Chenail
    March 1, 2018 at 2:11 pm

    Since all of the Amex cards have a once in a lifetime bonus rule, what do you recommend getting after those for more points?

    • Reply
      March 1, 2018 at 5:32 pm

      I believe the business cards don’t have a lifetime bonus rule, but I’d have to double check.

      I sure hope there will be more rewards credit card options for us Canadians.

      • Reply
        Nicolas Chenail
        March 2, 2018 at 6:08 pm

        I’m pretty sure all Amex cards do, it’s their credit card policy.

        • Reply
          March 3, 2018 at 1:39 pm

          Ah I have to double check that. This certainly limits how many rewards credit cards you can apply for in Canada.

Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.