Some of the places I remember most fondly were never the reason I started planning a trip. They appeared as airport codes in an award search: a connection between where we were and where we needed to go.
Normally, a connection is something to get through. But sometimes the flight routing makes me curious. What if, instead of spending a few hours in an airport, we gave that place two, three or four nights? Across five trips, that question took us to Taipei, Switzerland, Warsaw, Iceland and El Salvador. They were very different experiences, but each was worth more to us than an efficient airport transfer.
Four of these were historical Aeroplan bookings where adding the stopover cost us 5,000 points. The fifth, Iceland, was an Icelandair itinerary booked using Alaska Mileage Plan miles, with two nights added under the Alaska stopover policy at the time. I'm talking about what we actually booked—not promising those exact flights, prices or rules are available today. And the extra nights still meant paying for hotels, meals, transport and experiences.
Taipei: the connection I would happily have extended
Taipei entered the plan because I found an EVA Air redemption from Seoul to Singapore via Taiwan. For an additional 5,000 Aeroplan points on our booking, we turned that connection into three nights in Taipei. My expectations weren't especially high at the start. By the time I researched the city, I was looking forward to it—and by the time we left, I wished we'd stayed longer.
Our private tour took us to Jiufen and the remarkable rock formations at Yehliu. Taipei 101 was every bit as impressive as I'd hoped. The vegetarian food was a particular surprise: we ate exceptionally well, and the bubble tea certainly didn't hurt. There was far more to explore than we could comfortably fit into three nights. I would have welcomed a fourth just to wander the night markets and spend more time in the city.
Not every part of the stay was perfect. Grand Hyatt Taipei was convenient for Taipei 101, but it was showing its age. Even so, the city itself was the real revelation. Taipei is now somewhere I've recommended to family—an unlikely outcome for a stop that began as a routing opportunity.
Switzerland: a five-thousand-point stopover and one extraordinary mountain
Our route home from Manchester to Vancouver offered another opportunity. An Aeroplan redemption on SWISS and Lufthansa could take us via Zurich, and adding four nights in Switzerland cost an additional 5,000 Aeroplan points on that historical ticket. Switzerland was already high on my travel wish list, so it was one of the easier decisions I've made.
We arrived in Zurich late enough that we spent the first night near the airport before moving into the city. Over the following days we saw Rhine Falls, Lucerne, Grindelwald and Jungfraujoch. I enjoyed much of it, but Stanserhorn was the experience that surprised me most. We travelled by train, ferry, funicular and then an open-air gondola to reach the mountain. It felt like an entire Swiss travel advert unfolding in a single day.
I also learned that a brilliant stopover can still be planned better. Jungfraujoch was extremely crowded and, for me, didn't justify its cost. We spent more time travelling back to Zurich between day trips than I would have liked. If I repeated the journey, I'd try to arrive in one Swiss city and leave from another, rather than use the same base for everything. The four nights worked; the itinerary could have worked harder.
Warsaw: the compromise that stopped feeling like one
Warsaw wasn't the Polish city I originally had in mind. I had wanted Kraków, but when I found a LOT Polish Airlines routing from Rome to Toronto via Warsaw—FCO–WAW–YYZ—I could turn the connection into a two-night visit for another 5,000 Aeroplan points on our booking. I expected a compromise. Instead, Warsaw became one of the most pleasant surprises of that wider trip.
A private tour in a vintage Fiat was a wonderful introduction to the city. We saw historic buildings carrying traces of the Second World War and discovered public benches that played Chopin when you pressed a button. Our hotel, Nobu Warsaw, added its own memorable moments, including an excellent suite upgrade and cocktails good enough that one round became several.
The food produced a little twist of its own. Nobu's restaurant wasn't a good fit for our vegetarian needs, so we went elsewhere and found excellent ramen at Uki Green. That wasn't how I'd planned the evening, but it became part of what I remember fondly. Two nights felt about right, and I'm perfectly content with that visit. I wouldn't necessarily build a separate trip to Warsaw, but I'd happily choose it again if a flight took me through Poland.
Iceland: the stopover that earned a return trip
Iceland is the important exception to the Aeroplan examples. We booked Icelandair flights from Vancouver to Brussels via Keflavík—YVR–KEF–BRU—using Alaska Mileage Plan miles, and used the Alaska stopover policy applicable to our award to spend two nights in Iceland. It fitted into a wider journey that eventually continued into Europe and beyond.
Iceland already appealed to me, but even high expectations hadn't prepared me for the landscapes. The scenery began almost as soon as we landed. I still remember watching the sunrise on our drive towards Reykjavík. Between the volcanic terrain, geothermal areas, craters, geysers, waterfalls and the sheer drama of the views, two nights felt hopelessly short.
The Blue Lagoon was the weakest part for me because of the crowds, and almost everything—from restaurants to tours—felt expensive. Our Icelandair business-class seat wasn't lie-flat either. But that illustrates the point of this story: the highlight wasn't the airline seat or the theoretical value of the award. It was getting to experience a place we now absolutely want to revisit, ideally with enough time to see more of the country.
San Salvador: the stop we were unsure about became a favourite
The final example began with an Aeroplan journey back towards Vancouver. We had a routing via San Salvador—PTY–SAL–LAX–YVR—and added a two-night stop in El Salvador for another 5,000 Aeroplan points at the time. Of all these stopovers, it was the one I was most apprehensive about beforehand. I'd heard enough about the country's safety challenges that I wasn't sure what to expect.
What stayed with us, though, was the landscape and how much we enjoyed the visit. The volcanoes and El Boquerón were extraordinary, and our tour with Eco Tours Petate gave us a memorable introduction to the country. I would rather have spent another night here than added a night in Panama. It ended up being our favourite city stop on that particular trip.
There were practical surprises too. At the airport, we had to order a meal using Google Translate, passing the phone back and forth to explain each item. Experiences like that reminded me not to take English-language convenience for granted. I wouldn't generalise from one trip about conditions across El Salvador, and I'd still check current advisories and make sensible plans before visiting. But I'm glad we didn't let uncertainty automatically turn this into a same-day connection.
A stopover isn't a free holiday
The easy version of this story would be to say that four cities cost us 5,000 Aeroplan points each and Iceland came courtesy of Alaska miles. That's true of those specific historical bookings, but it leaves out the hard part. A stopover asks you to spend additional days of a finite trip. It can add hotels, food, local transport, touring costs and some welcome complications. And any award ticket still needs to be available and bookable under the rules in effect when you travel.
The reward isn't automatically the lowest number of points. In Zurich, the extra days opened up Switzerland. In Taipei, they turned an airline connection into a city we recommend. Warsaw challenged my expectations. Iceland gave us a place we want to explore properly. San Salvador gave us one of the biggest surprises of that trip. Those are very different outcomes, and that's why I wouldn't force every convenient connection into a holiday.
Before making the same decision today, I'd check the current stopover rules and ticket pricing, the actual routing, entry requirements, arrival times, luggage arrangements and what the extra nights would displace. An appealing stopover only becomes worthwhile once there's something on the ground I genuinely want to experience.
The itinerary got us there. The destination did the rest.
Looking back, I don't remember these places primarily as clever redemptions. I remember the views from Stanserhorn, the unexpected food in Taipei, the yellow Fiat in Warsaw, Iceland's volcanic landscapes and the feeling of discovering something in El Salvador that I'd nearly skipped.
Points helped us turn connections into real trips. But points weren't what made those extra nights valuable. The places themselves did.