Blog5 country European stopover summer holiday

5 country European stopover summer holiday

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Greg·July 9, 2026·3 min read

This was my first serious Aeroplan redemption and did I ever put the work in to plan this one. I spent weeks looking at possible routing and was very happy where I ended up. Everything was in economy, but that didn't bother me one bit at the time. Now that I've experienced long-haul business class, I might have a different opinion of course.

This trip made use of several layovers (stops less than 24 hours) as well as an open jaw (flying home from a different airport - not a round trip), as well as a stop-over.

This was all booked on a single redemption of about 60,000 points and $234 of taxes and fees.

If that sounds too good to be true, this trip happened in 2019, so the details are a little fuzzy, but here's what I remember happening. =D

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European Getaway
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120,000 pts
$234.00 taxes
7 segments

Starting out from Winnipeg, the first stop was during the day in Chicago. Jumped on the elevated train and hit the art museum before grabbing some refreshments in a little cafe near the museum. Then back on the train and off to London, UK!

I had about 24 hours in London, and spent most of it just doing basic tourist things, checking out Big Ben and the London Tower, walked past the Big Eye, grabbed some ice cream by the river, walked through Camden and hit up a couple of pubs before heading back to Heathrow airport.

From there I landed in Frankfurt which is the first time I had a bus trip back to the terminal. Frankfurt was really just a quick pit stop to get me into central Europe. I made my way to the central train station, Frankfurt (Main) Hauptbahnhof, and grabbed a quick lunch on a nearby pedestrian street. From there it was on the train and off to Florence.

If you haven't been on a high-speed train, I highly recommend it. The comfort and roominess far surpass any economy seat on an airplane, and everything just feels much less stressful when you're not stuck in a flying tube.

Florence is amazing of course, the food, the art, the markets, and all of it completely walkable, no need for a car, just watch out for the thousands of Vespas whipping around the city and down back alleys. These is a large indoor market in Florence which has all sorts of food and artwork. I have no idea if it's still there, but there was a booth making fresh pasta and you could choose the type of noodle and the sauce. It's still the best pasta I've ever had.

I spent some time in the Tuscan country-side visiting wineries and watching amazing sunsets with a glass of wine before returning to Florence to continue the trip.

From Florence I flew to Lisbon and spent about 48 hours running around the the city, doing an electric bike tour (highly recommend!) and taking a train out of the city to a beautiful beach.

After Lisbon it was back to Canada with a quick overnight in Toronto, only had time to watch the Raptors in the NBA finals at the hotel before finishing the trip back to Winnipeg.

This trip was a total of 15 days, so I got to see and do a ton of stuff in that time for an amazing deal, something that can only be done with points!

Hopefully this inspires you to go out and book your next travel points redemption and make some memories!