The Crazy Aeroplan Redemption I Booked But Never Flew

Would you fly an itinerary if you got to be on 5 new airlines, fly to 5 new airports, at the cost of no proper sleep for more than 30 hours, and have a total trip time of ~50+ hours for what would ideally be less than 12-14 hours on a more direct route?

As an introduction, I got into the miles-and-points game in late 2022. Guided by this blog and similar sources including channels, forums, and videos, I went deeper and deeper into stretching my miles and points. I have developed a penchant for flying, traveling, and maximizing all the random flight stats I can, with the limited time and resources available to me outside my regular day job. My first international redemption, as luck would have it, was the fabled Q Suites in 2023.

We fast-forward to January 2025 with this background. By that time, I had already used Aeroplan a couple of times for my domestic and international travels. I was now looking to see how I could get even more value from it. I had a trip to Portugal planned for June and had already applied for and received my Schengen visa. My flight from Lisbon back to Mumbai was booked on Qatar Airways using AA points transferred from Marriott (had and have never flown to North America or on any airlines based there, score one for transfer partnerships), with the itinerary beginning on 23rd June with LIS => DOH => CMB => BOM. Well, kinda boring.

I remember reading about Ben’s Aeroplan whirlwind adventure in one of his linked posts at that time, and it got me thinking, wait, can I replicate it somehow? So, I decided to follow through.

For the purpose of this story, I would like to keep the basics simple:

1. Aeroplan allows six sectors in one itinerary
2. The distance you travel across six sectors cannot be more than twice the distance between the city pair (so with LIS – BOM at 4,989 miles, my max could be 9,978)

An added complexity for me was that mine was a single-entry Schengen visa, with a hard limit on the duration I could spend in the region, so by 24th June I needed to be processed out of the region. Additionally, I could not backtrack and fly within the Schengen region once I was out.

With these constraints in mind, I got cracking. For those looking to replicate, gcmap is your dearest friend. I tried to build out multiple itineraries, running the Aeroplan search in parallel across various city pairs to check award availability and layover lengths. I wanted to build in buffers in case there were any delays in preceding flights, to ensure the subsequent trip didn’t get butchered, given the complexities involved.

After a weekend (well spent as per my POV), I had my itinerary ready, which would typically be a nightmare for any sane person. I would be taking the train down from Porto to Lisbon to kickstart the proceedings on the afternoon of 22nd June.

The flights (all times local) to follow would be:

1. LIS – MAD on TAP Portugal (departing 19:05, arriving 21:25)
2. MAD – ATH on Aegean (departing 1:20 on 23rd, arriving 5:45)
3. ATH – FRA on Lufthansa (departing 11:40, arriving 13:45)
4. FRA – VIE on Austrian (departing 15:50, arriving 17:15)
5. VIE – ADD on Ethiopian (departing 22:05, arriving 5:25 on 24th)
6. ADD – BOM on Ethiopian (departing 18:20, arriving 2:05 on 25th)

Considering the first four legs were in European business class (middle economy seat blocked), I had to accept that my first proper sleep after waking up on the morning of the 22nd would come only on the night of the 24th. However, the attraction for me was that I had never flown these airlines before; I would have access to their Schengen business-class lounges, six entirely new routes, and 5 new airports (excluding LIS and BOM, of course). The added benefit of this trip was that, because the Ethiopian transit was long enough, I could get a complimentary stay at their transit hotel. So I was looking forward to that too.

For ticketing this itinerary, just consider this article as your go-to. I called at the exact opening time and was connected quickly. I had a NATO phonetic chart in front of me because, due to differences in accents, I always prefer to give IATA codes for airports and destinations. I informed the agent that I wanted to book a multi-leg itinerary, and the agent was efficient and kind enough that it all happened in one go. We went through each leg one by one, with me providing the specific flight number and airline I wanted to book with.

Ultimately, the agent confirmed it would cost me 80k Aeroplan points and 192.40 CAD to book the entire itinerary in business class (as an avgeek, a steal). Ticketing was processed, charges were deducted, and I got the confirmation email.

Now coming to the second part of the headline. I ultimately didn’t fly this, because I found an even juicier experiential redemption for me. So that got booked; this got canceled. As luck would have it, I would end up canceling that too, for the best-ever redemption I have done. But maybe that’s for another story.

What do you guys think, though? Would you fly such an itinerary and basically spend 50+ hours in airports and on nonstop flights?