An award flight put Istanbul on our itinerary. Santorini was the place we refused to sacrifice. Budapest was the city we didn't give nearly enough time.
I did not sit down to plan a trip to Istanbul, Santorini and Budapest. I sat down to see whether I could find an interesting redemption that would get us to Europe.
The first search was through Aeroplan. It led me to a Vancouver–Chicago–Istanbul itinerary, with United Airlines for the short Economy leg and Turkish Airlines Business Class across the Atlantic. But when I compared booking options, Turkish Miles&Smiles offered the more attractive redemption. The flight made Istanbul a place worth considering. From that one decision came an eight-night itinerary across three very different destinations.
It was not a neat, entirely points-funded holiday. We used multiple loyalty programmes, paid cash where that made sense and passed up one city we would otherwise have liked to see. In the end, the stop that began the planning was not the one I most wanted to revisit.
The award that changed the map
Dream Lux TravelsOur April 2024 outbound booking cost 45,000 Turkish Miles&Smiles miles plus C$338 per person, using miles transferred from Capital One. From Vancouver we flew United Economy to Chicago and then Turkish Airlines Business Class to Istanbul.
The Turkish flight was one of the reasons I was excited about the booking. Its spacious seat and generous food service, with a chef taking orders in the cabin, made the long sector memorable. Service was efficient rather than especially personal, but the onboard meal experience lived up to the airline's reputation for us.
I would not treat 45,000 miles as a current price or assume the same award can be recreated. Even then, it was a particularly appealing opportunity. Its larger effect was on the itinerary: Istanbul was not somewhere I had been determined to visit, but the redemption made it our natural starting point.
Once that flight was booked, I began looking for what could come next. Athens was an option. Santorini was something more than an option. Our eventual regional routing would put us on Aegean Airlines Business Class, connecting Istanbul–Athens–Santorini and later Santorini–Athens–Budapest. I used Aeroplan points for both Aegean itineraries: around 60,000 points in total for the two of us. We had found another way to build the trip with miles—without sacrificing the time we wanted in Oia.
The destination we would not give up
Santorini had been on our wish list for years, and Oia was the experience I cared most about protecting. We wanted to stay there, not simply arrive with a group for a few hours and leave after the famous sunset.
Getting the flights to line up was more awkward than it first looked. Our Aegean Business Class itineraries ran IST–ATH–JTR on April 6 and JTR–ATH–BUD on April 9, so Athens was part of the flying regardless. The question was whether to turn one of those connections into a stopover and actually explore the city. Aeroplan allowed eligible international stopovers for additional points; it was not an impossible idea. But the flight dates we could use meant that giving Athens real time would have taken two days from Santorini or at least one from Budapest. Neither compromise appealed to us.
So we decided to connect through Athens, rather than stay in Athens, without pretending we could experience everything Greece had to offer on that trip. I had already reserved our Oia hotel while the flights into Santorini were not yet available to book. Waiting for those flights to open was the nerve-racking part of an itinerary that looked much simpler on a map than it was to assemble.
It was an early lesson in what I think good points planning actually involves: a useful redemption is only a starting point. The harder decisions concern the time and experiences you're willing to protect.
Istanbul: glad we went, not eager to repeat it
We arrived in Istanbul on April 3 and spent three nights at Hagia Sofia Mansions, booked for 210,000 Hilton Honors points in total. Our accommodation felt more like a two-level private residence than a conventional room, with Hagia Sophia just a short walk away. Being able to explore the historic district on foot made this an excellent base for those few days.
The Blue Mosque more than justified a visit. Its scale and detail were even more striking inside than in photographs. Another favourite memory came without a reservation: while looking for something to eat around Galata and Karaköy, we came across a Bosphorus cruise and decided to go. Seeing Istanbul from the water was one of the nicest parts of the stay. The baklava from Karaköy Güllüoğlu was another exception in a dining experience we otherwise found difficult as vegetarians.
Not everything worked. Busy tourist areas brought persistent selling, and some interactions left us less comfortable than we had hoped. My partner and I did not always read those encounters the same way, and I would not extrapolate our experience to everyone in the city. But it coloured how relaxed we felt there.
Three nights were enough for our particular priorities. I am glad the award led us to Istanbul; I am not especially eager to return. That is not the same thing as regretting the stop.
Read the standalone Istanbul journal, including the full firsthand verdict on the mosques, hotel and Bosphorus afternoon.
Oia: the place I still think about
Dream Lux TravelsOn April 6 we reached Santorini and checked into Canaves Oia Suites for three nights. We had used 105,000 World of Hyatt points in total for a Superior Suite with a plunge pool, overlooking the caldera. It was the room we had booked, not a surprise elite-status upgrade, and it was extraordinary enough without one.
I remember our first view from the property and then the moment we stepped into our suite and looked out across the water. I had spent years seeing photographs of Oia, but I had not expected the real thing to be that affecting. A private pool and a caldera-facing terrace turned the stay itself into the main attraction. The hotel breakfast, a welcome drink and even simple meals we brought back felt better because of where we were sitting.
We did not book an elaborate series of tours. We walked through Oia, took in the view and had time simply to be there. When we later tried the popular public sunset viewpoint, the crowd made the contrast unmistakable. We'd already enjoyed the scene from the privacy of our accommodation, without competing for a space among the people who had arrived well in advance.
There is one practical caveat I would give anyone looking at photographs and imagining effortless luxury: Oia's steps and slopes are real. Getting around requires more energy than the postcard version suggests. We also found arranging reliable airport transport valuable.
Of the three destinations, this was the one that exceeded my highest expectations. Three nights felt right. I would return to Oia for the view alone, even knowing there are other places around the world we have yet to see.
I planned the Canaves booking deliberately. I had World of Hyatt Globalist status at the time and knew Hyatt's partnership with Small Luxury Hotels of the World was coming to an end. I therefore used our Hyatt points to secure three nights at Canaves Oia Suites while that booking opportunity still existed. The partnership ended on May 15, 2024, just weeks after our stay. It was a window I chose to use, not a lucky coincidence.
Read the standalone Santorini journal for the complete Oia and Canaves experience.
Budapest: the good flight home that became the problem
Dream Lux TravelsBudapest entered the itinerary in a much less romantic way. I found a useful return award to Vancouver from there, flying KLM Business Class via Amsterdam. My sister had spoken highly of Budapest, so the city was easy to justify as the final stop. We gave it two nights, April 9–11.
What a mistake that limit turned out to be—not because the stay was poor, but because we loved it too much to leave so quickly.
We stayed at Matild Palace in Pest. One night cost 63,000 Marriott Bonvoy points and the other €389.13 in cash. We booked a Deluxe King Room and, as Marriott Bonvoy Platinum members, received a One Bedroom King Suite. The upgrade was a wonderful surprise, but one I would never imply is guaranteed. The hotel's architecture, location and breakfast made it a memorable stop in its own right.
Outside the hotel, we were struck by Budapest's grandeur, particularly on the Pest side. Our private tuk-tuk tour gave us a practical way to connect the sights across a sprawling city. And walking beside the Danube as evening arrived, seeing the illuminated buildings and Buda Castle across the water, was one of the finest moments of the entire holiday.
The tour did not make two nights adequate. It made the city feel bigger—and made us realise how much we had only sampled. Next time I would spend longer exploring both Buda and Pest, perhaps staying in each. My partner would rank Budapest among her favourite cities; it is certainly very near the top of my list too.
Read the standalone Budapest journal for the full hotel, tuk-tuk and Danube experience.
What we actually spent points on
A three-city points itinerary is easy to oversimplify as a series of free flights and free hotels. Ours was neither.
- Outbound to Istanbul: Turkish Miles&Smiles, 45,000 miles + C$338 per person, for United Economy Vancouver–Chicago and Turkish Airlines Business Chicago–Istanbul. We transferred Capital One miles to Turkish.
- Istanbul hotel: 210,000 Hilton Honors points total for three nights at Hagia Sofia Mansions.
- Aegean regional Business Class flights: I used Aeroplan points for both Aegean itineraries: around 60,000 points in total for the two of us. We flew Business Class on Aegean for both IST–ATH–JTR and JTR–ATH–BUD.
- Santorini hotel: 105,000 World of Hyatt points total for three nights at Canaves Oia Suites, including the plunge-pool suite we booked. This was possible through the former Hyatt–SLH partnership, which ended May 15, 2024.
- Budapest hotel: 63,000 Marriott Bonvoy points for one night, and €389.13 for the second at Matild Palace.
- Return to Vancouver: KLM Business Class Budapest–Amsterdam–Vancouver through Flying Blue, ultimately 50,000 miles + US$293.80 per person. I'd originally booked the award at 80,000 miles per person and later paid US$56 per ticket to change it when a lower points price became available.
Meals, tours, transport and other travel costs were paid separately. Our points came from different programmes, each used for a different part of the journey.
What the bookings gave us was the ability to put money and time towards the moments that mattered most: a stay in Oia we would not have casually booked at the prevailing cash cost, a distinctive hotel in Istanbul, and room in the budget for experiences such as Budapest's private tuk-tuk tour.
What I'd change about this itinerary
I would not add Athens at the expense of Oia or Budapest. Skipping an attractive destination felt like a compromise when we were planning; it proved to be one of the decisions I most agree with in hindsight.
I might shorten Istanbul to two nights if our arrival time and sightseeing priorities allowed it, though we were glad to have seen the city properly. I would keep at least three nights in Oia. And I would give Budapest substantially more time—certainly more than the two nights we gave it.
The redemption that started this trip was excellent. But it wasn't the best part of the journey, and it wouldn't be what I'd use to decide our next visit. One city was a worthwhile introduction, one island was everything I had hoped, and the final stop reminded me how easily an itinerary can be too efficient for its own good.
Points helped draw the map. The experiences told us where we should have stayed longer.