How I Booked a Year’s Worth of Travel on Points

Sometimes, the most challenging part of travelling on points is what to do after you’ve gone through the trouble of earning them.

If you travel as a family or in a group, you’ll need to start off by planning in advance, especially if you’re looking for several award seats.

My family takes several trips a year, and I typically start planning our trips one or two years in advance. Two years gives me enough time to earn the points I need, and then I start booking approximately 11 months out from my travel date, especially on high-demand routes.

In this article, I’d like to highlight the trips I’ve planned out for the year, and how I’ve used my credit cards and award points to offset the costs.

Some of my redemptions may not be the best options or most valuable, but they’re ones that worked well for my family, based on the points that we’ve earned and credit cards that we have.

In This Post

Big Island, Hawaii

Hawaii is a popular destination for North Americans, and the cost of flights can quickly add up, especially during peak travel holidays.

Luckily, there are many ways to redeem points for travel to Hawaii, and a bit of planning in advance can help you get there for less.

Hawaii is a popular destination for North Americans

For our flight going to Kona from Toronto, we booked using WestJet dollars and the annual companion voucher that comes with our WestJet RBC® World Elite Mastercards.

Normally, it’d make sense to book a round-trip flight if you’re using a companion voucher, as there’s usually a $399 fee for the companion to use the voucher to Hawaii.

However, a couple of years ago, WestJet ran a promotion in which they offered a special companion voucher with a $0 base fare for a second passenger. All I had to pay were the taxes and fees for the companion ticket, and there was no cost for the base fare.

In the end, our redemption for Toronto to Kona for five passengers looked like this:

  • Two companion vouchers
  • 439 WestJet dollars × 3 passengers (we chose the EconoFlex fare just in case we needed to make changes)
  • $117.10–157.10 (CAD) taxes and fees × 5 passengers

In other words, by making use of our companion vouchers and WestJet dollars, the total out-of-pocket cost for five people was less than $800 (CAD), which is pretty good.

Coming home from Kona to Toronto, we redeemed $1,560 (USD) from our United Travel Banks to cover our United Airlines flights back.

The biggest takeaway from booking this trip: take advantage of promotions whenever they come up, as they can wind up paying dividends down the line.

Hong Kong and Japan

My grandma is turning 90 this year, so our family will be heading back to Hong Kong to celebrate with her. Although there are many options to get to Asia, for convenience, I wanted a direct flight there.

In the past, I would have booked Cathay Pacific through Alaska Airlines Mileage Plan; however, Cathay Pacific hasn’t been reliably releasing any long-haul award space to any of its airline partners for the past few years.

Cathay Pacific award availability isn’t great these days

The only reliable way to book Cathay Pacific award flights these days is through Cathay Pacific Asia Miles, its own award program.

Asia Miles can be acquired through transferring RBC Avion points at a 1:1 ratio, which I earned with my RBC® Avion Visa Infinite†, or by transferring American Express Membership Rewards points at a less favourable 1:0.75 ratio, which I earned mainly from my American Express Cobalt Card.

Knowing I had this trip coming up, my husband and I both signed up for the new Cathay World Elite Mastercard – powered by Neo, which came with a welcome bonus of 45,000 Asia Miles.

Then, for our flight from Toronto to Hong Kong, we redeemed the following:

  • 38,000 Asia Miles for economy class × 3 for the kids
  • 75,000 Asia Miles for premium economy class × 2 for my husband and me
  • $224.50 (CAD) taxes and fees x 5 passengers

Coming back, we booked a direct Air Canada flight from Tokyo to Toronto using Aeroplan points.

Between the two of us, we were able to use eUpgrades to get the whole family into Air Canada business class using the Latitude Attitude.

For this leg of the trip, we redeemed the following:

  • 74,800 Aeroplan points × 5 passengers
  • 13 eUpgrades × 5 passengers
  • $36.40 (CAD) taxes and fees × 5 passengers  

I haven’t booked our flights from Hong Kong to Tokyo yet, but likely we’ll be paying cash for this, in the range of $300 (CAD) per person.

Round-trip tickets right now on Cathay Pacific are pricing out at $2,700–3,100 (CAD) in economy class, so I feel that we get an excellent deal by using points.

The biggest takeaway from booking this trip: working in two-player mode and having flexible points gives you the best options for booking trips on competitive routes.

San Diego and National Parks

In the summer, we’re heading to California for a bit of time with extended family.

Friends are always telling us what a great family destination San Diego is, and since our trip to Zion National Park in Utah, we’ve also been wanting to explore more national parks, so we decided to cross both off our list.

We booked our flights flying into Los Angeles from Toronto, and plan on driving up to Sequoia and Kings Canyon National Parks.

From there, we’ll catch a short flight back to San Diego, and spend some time there before heading back up to Toronto.

Sequoia National Park

For our flight from Toronto to Los Angeles, we booked a direct flight in economy using Aeroplan points, for the following costs:

  • 9,400 Aeroplan points × 5 passengers
  • $107.20 (CAD) taxes and fees × 5 passengers

For our flight coming back from San Diego to Toronto, we booked a direct flight in economy using Aeroplan points, for the following costs:

  • 12,400 Aeroplan points × 5 passengers
  • $76.30 (CAD) taxes and fees × 5 passengers

At the time of writing, this itinerary is pricing out at $699 (CAD) per person, which means I’m getting a value of 2.23 cents per Aeroplan point, which I mostly earned from my American Express Aeroplan Reserve Card.

For our short flight from Fresno, the closest airport to Sequoia, to San Diego, it’ll cost $125 (CAD) per person.

For this, I plan on booking through Expedia® for TD and cashing out my TD Rewards Points earned through my TD First Class Travel® Visa Infinite* Card

The biggest takeaway from booking this trip: booking in economy can still result in great value for your points, and having fixed-value points comes in handy for offsetting other travel expenses.

New Zealand

My husband and I had a work conference pencilled in for New Zealand later this year.

As luck would have it, Air New Zealand, which is a notoriously difficult airline to book on points, decided to release a bunch of award seats a few months ago that happened to coincide with our travel dates.

Air New Zealand business class

Air New Zealand is a Star Alliance airline, and I was able to secure our flights there using Aeroplan points.

However, I also managed to book the return flights through Virgin Atlantic Flying Club, leveraging the separate partnership between the two airlines.

Air New Zealand doesn’t fly to Toronto, and I had to book from Houston to Auckland and back.

For our flight from Houston to Auckland, we redeemed the following:

  • 75,000 Aeroplan points for Air New Zealand business class × 2 passengers
  • $132.90 (CAD) taxes and fees × 2 passengers

For our flight from Auckland to Houston, we redeemed the following:

  • 62,500 Virgin Points for Air New Zealand business class × 2 passengers
  • $61.99 (CAD) taxes and fees × 2 passengers

If you’re wondering how I accumulated my Virgin Points, it was once again through my Amex US cards.

In the last couple of years, there have been a couple of 30% transfer bonuses from Amex US Membership Rewards to Virgin Atlantic Flying Club, which I took advantage of. 

Initially, the intent was to use them to book an ANA First Class flight, but that didn’t work out, so I jumped at the opportunity to use them for Air New Zealand instead.

Factoring in the transfer bonus, my business class redemption was only 48,077 Amex US MR points per ticket, which is outstanding.

Without taking into consideration the short positioning flight I still need to book from Toronto to Houston and back, we scored an astronomical value from our credit card points for this redemption.

The biggest takeaway from booking this trip: leverage transfer bonuses whenever you can, and keep an eye out for award availability with airlines that are difficult to book.


For our final big trip of the year, we’re going to Morocco. This is a couples’ trip we had planned before the pandemic happened, and was cancelled because of it. Needless to say, I’m glad we can finally go.

Initially, the plan was to use our Aeroplan points for the redemption. Air Canada offers direct flights from Montreal to Casablanca, and flying back, we’d fly TAP Air Portugal from Marrakech to Toronto, with a short layover in Lisbon.

For our flight from Toronto to Casablanca via Montreal, we redeemed the following:

  • 57,800 Aeroplan points for business class × 1 passenger
  • 64,300 Aeroplan points for premium economy × 1 passenger
  • 11 eUpgrades × 1 passenger
  • $65 (CAD) taxes and fees × 2 passengers

Unfortunately, while waiting for our friends to accumulate enough points for the return flight, the TAP Air Portugal award seats disappeared on the dates we needed.

Luckily, we found a flight on British Airways that worked on our dates, with several seats available.

The rates from British Airways Executive Club weren’t great, so instead, we used American Airlines AAdvantage miles to make the redemption.

Unfortunately, the taxes and fees were hefty, since we were going through London, but overall it was still good value for a business class redemption, and it allowed us all to travel together.

The taxes and fees on flights with British Airways can be steep

We acquired the AAdvantage miles through transferring our RBC Avion Rewards earned from our RBC® Avion Visa Infinite† cards at a 1:0.7 ratio. 

For our flight from Marrakech to Toronto via London, we redeemed the following:

  • 57,500 AAdvantage miles for business class × 2 passengers
  • $484.70 (CAD) taxes and fees × 2 passengers

The cheapest flights for our dates were more than $4,500 round-trip, which gave us a value of over 3 cents per point in either currency.

The biggest takeaway from booking this trip: even with high taxes and fees and less-than-ideal transfer ratios, booking premium flights can still result in great value for your points.


Hopefully, this article has helped to highlight how holding different Canadian and American credit cards, as well as earning different point currencies, can be used for various trips near and far.

Keep in mind these are just a few examples of the countless possibilities of where your redemptions can take you.

For our trips this year, we redeemed a grand total of just over 1.2 million points and miles, two WestJet companion vouchers, 76 Air Canada eUpgrades, plus other reward points and credits from our credit cards to make it all happen.

Having multiple points currencies and booking early are keys to giving you the most flexibility and the greatest success in making the flight redemptions you want.

While Canadian credit cards will cover a majority of your travel plans, US credit cards will give you greater access to other airline programs that can allow you to book similar flights for an even better value.

Here’s to happy travel planning for 2024 and beyond!

  1. Ana

    I love your posts because we usually travel as a family. Planning 2 years in advance makes sense, but the anticipation… lol!

    Our year started (or, 2023 ended) with a trip for 4 to Brazil over the holidays using Latitude Attitude (had to book that 11 months in advance). March break in Mexico using MR/Delta/WJ for the flights with 2 free nights at the Hilton. Was offered the Hilton time share offers and, thanks to what I learned from you, took them and we will be going to Big Island and Honolulu – planning to use RBC Rewards Fixed Redemption for the flights. Now need to figure out what to do over the holidays! Thanks for the constant inspiration!

  2. Tom

    How do you usually meet the MSR for so many cards?

    1. christopher

      You don’t them all at the same time of course, but if you plan you game properly, you can meet one MSR after another. Don’t just get the cards that you think is good, think about if you can utilize it efficiently

  3. MurrayF

    Great article, very worthwhile reading thanks. shame I missed those flights to NZ. I am seeing occasional first class on AA from BOS and JFK via LAX and SYD to Auckland for 90-110,000 each way which is pretty good vs the standard 450k, even though it’s only American first class. would be nice to do it once before it dissapears.

  4. David

    Two questions.
    1 How long did it take to save all those different points?
    2. Do you maintain all those credit cards yearly?

    1. Amy YYZ

      Hi David. Some currencies are easier to earn than others. In general, I’d say it takes 1-2 years to earn the point balances I need for my trips, depending on how many I take in a year and where I’m travelling. As long as I see value in a card, yes, I will keep the card.

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