Success Story: Alex’s “Stitched-Together” Aeroplan Family Getaway

The Reader Success Story for the month of October 2019 features Prince of Travel reader Alex K., who shared with me his experience redeeming Aeroplan miles for the first time.

The realities of his travel goals certainly didn’t make things easy for him: he needed to fly his family of four over to Israel, while he himself needed to slot in a 24-hour layover in Moldova along the way, all while doing his best to avoid fuel surcharges. You’ll find his story reproduced here, with a few of my comments below the fold. 

Hey Ricky,

I wanted to share my first award ticket booking with Aeroplan.

We are two adults and two kids, and we were talking about flying on a pretty complicated trip sometime in August 2020.

We wanted to leave from Toronto to someplace in Europe, where we would split ways: I would continue to a layover in Chisinau, Moldova (a short personal visit), while the rest of my family would continue to Tel Aviv, Israel.

Later on, I would join the family in Israel for a 10 day vacation. When we finish, we wanted to spend four nights with a couple of friends in Porto, Portugal before flying back home to Toronto.

I have taken the task to create this complex routing using the tips, guides, comments and other information available on Prince of Travel, and it was really a blessing to have access to all that knowledge!

For this Aeroplan booking, our origin would be Toronto and our destination would be Tel Aviv. I have checked the maximum permitted mileage (MPM), which is 9,561 miles. Tel Aviv is in the Middle East, so according to the Aeroplan chart, it would cost us 165,000 miles per person on a business award – a whopping 660,000 miles in total for four people. We only had 360,000 miles on hand, so we decided to bite the bullet and fly in economy.

Since the only direct flight to Tel Aviv is with Air Canada, and we wanted to a) save on fuel surcharges and b) fly together as a family on the transatlantic leg to Europe, we needed to find the connecting airport from which we would be able to continue to both Chisinau and Tel Aviv.

While Tel Aviv is connected very well to most European airports within the Star Alliance, Chisinau turned out to be a problem. I checked Chisinau’s airport to see which inbound and outbound flights are there at all, and found Vienna, Warsaw, and Istanbul as suitable candidates.

Flights from Toronto to Vienna were with Lufthansa or Austrian Airlines and their enormous fuel surcharges, while there were no available flights to Istanbul from Toronto, Montreal, Chicago, Washington, New York, or Boston in economy.

Toronto–Warsaw on LOT Polish Airlines turned to be our lucky choice: there were plenty of seats in both economy and business on their Boeing 787-9.

Then, I decided to work on plotting our way back from Tel Aviv to Toronto with a four-night stopover in Porto, Portugal, and I would come back to arrange the journey from Warsaw later on.

I couldn’t find direct flights from Lisbon (3 hours away from Porto) to Toronto, so I decided to take a flight with a long layover in Chicago and to enjoy its downtown. It was with TAP Air Portugal on their new Airbus 330-900neo, so again we’ve saved on the surcharges and would fly on a newer airplane.

At last, I came back to stitch the last piece of the puzzle, and while the flights from Warsaw to both Chisinau and Tel Aviv weren’t elegant, I was able to make them happen on a combination of Austrian Airlines and Turkish Airlines.

I called the Aeroplan phone number, and after 45 minutes of waiting for a customer service representative, I have triumphantly booked it all!

It cost me 80,000 Aeroplan miles per person (320,000 miles in total), plus roughly $1,500 in taxes and fees for the four of us.

Afterwards, I calculated how much I would have to pay out-of-pocket if I were to pay with cash on the most basic flights with any airline – this routing would have cost our family around $8,000 ($2,000/person, and realistically as much as $2,500/person), so I consider 320,000 miles + $1,500 a very good deal.

I had gathered the 360,000 miles in 9 months of TD and CIBC Aeroplan personal and business cards, as well as the Amex Gold personal card, with zero annual fees for all those cards across both myself and my wife.

I used the five-day free trial of the ExpertFlyer premium service – and this tool is absolutely essential! I will team up with a few more friends to share this account in the future.

While it is not exactly a crazy round-the-world trip to dream destinations, it is the itinerary we needed, and it was very satisfying to be able to stitch together this puzzle!

Thank you Ricky for providing all the resources, and thank you to all of you who leave valuable comments in the blog!

As we all know, flexibility is key when redeeming miles for travel, and I’m impressed with the ways in in which Alex was able to draw upon this principle as he sought to stitch together his booking.

First, he put in the time to do his homework and figure out which airlines would work best for his goal of flying his family over to Europe without paying surcharges. Then, by maintaining a level of flexibility among those airlines, he was undeterred when a few of them came back without award availability, and was eventually able to find space on the Toronto–Warsaw flight by LOT Polish Airlines.

On the return journey, Alex was again faced with a lack of direct flights between Lisbon and Toronto on TAP Air Portugal. Whereas the average traveller might find themselves frustrated at having to endure an additional connection or two, but Alex was able to see the bright side of things, scheduling a longer layover in Chicago to get an additional destination out of it, which is sure to make the family trip even more memorable.

Alex’s redemption also goes to show the sheer power of Aeroplan across the board when it comes to travelling internationally.


Whereas many of the other programs in the Canadian landscape are only best-suited to travelling to specific destinations on specific routes, Aeroplan’s access to the vast Star Alliance route network allowed Alex to effectively plan a trip that will take him to Moldova, Israel, and Portugal. 

You’d be hard-pressed to find another program that offers nearly quite as much flexibility; moreover, even though the highest value of your Aeroplan miles is naturally unlocked when fly in premium cabins, these trips can get pretty expensive when travelling in economy too, and Alex demonstrated that you can still achieve a respectable 2+ cents per point (cpp) even when flying economy.

Achieving these outcomes on Aeroplan, however, will require understanding how to use the program properly beyond what the search engine spits out.

Thanks for sharing, Alex, and I’ll be sending you 5,000 Aeroplan miles as a reward to get you closer towards the next big trip. 

And if you’d like your story to be featured too, send me an email with “[Success Story]” in the subject line for a chance to be selected for the November edition!