Booked: The City of Roses

Jessica and I have been back home for about two weeks now, doing our best to enjoy the last few days of the lovely Toronto summer. Having said that, it does feel somewhat as though our round-the-world adventures over the summer have raised our appetite for adventure to unprecedented levels, because when a block of time opened up in our schedules for this upcoming weekend, our first instinct was to plan a quick trip to spend a relaxing long weekend somewhere.

The Trip

For this getaway, our primary goal was to see a new part of the world – preferably somewhere close to home – while taking things at an easy-going pace.

We considered – and vetoed – a host of possibilities. New Orleans? It’s been on my bucket list for a long time, but Hurricane Gordon was in town and ready to make its presence known. Havana? The language barrier was at odds with the idea of an “easy” trip. Montreal? Always a good idea, but a little too close to home for our liking.

After plenty of deliberation, we eventually decided on Portland, Oregon, which is a place that we’ve both been wanting to visit.

I do love spending time in the Pacific Northwest – Vancouver is my birthplace after all, and Seattle is a place I hold dear having visited last year and the year before.

Portland is the last major city in the region that I’ve yet to visit, and it’s always struck me as the youngest sibling of the PNW, making up for its smaller size with a strong cultural output and a hip, forward-thinking attitude. 

I mean, come on – Portland is known for excellent microbrews and food trucks, its eminently cycle-friendly streets, and the picturesque hiking trails in its backyard. If that doesn’t make for an ideal long-weekend getaway, I don’t know what else would!

The Flights

Booking domestic or transborder flights within North America has always been a bit of a pain point for those who like to redeem rewards points for travel, because often times the value proposition of doing so can be rather unclear.

First of all, I’m not fussy at all about spending four or five hours in economy class (access to Priority Pass lounges makes the economy experience all the more palatable), nor am I particularly eager to splash my hard-earned miles on middling domestic business class seats on narrowbody aircraft. As a result, I almost never find it worthwhile to redeem points for business class within North America. 

Pay double the miles for these seats? Nah...

Pay double the miles for these seats? Nah…

That leaves the possibility of redeeming points for an economy ticket, such as 25,000 Aeroplan miles for a roundtrip between Toronto and Portland. This could be a good use of Aeroplan miles in certain situations, such as if you were to add a stopover to the journey in order to visit two cities instead of one. However, this time around we simply wanted to spend our time exploring Portland and had no plans for a stopover, so that’s moot in this scenario.

What’s the alternative? Since I was booking this trip pretty close to the date of departure (this past Monday, to be exact), cash prices were already looking pretty high, at around $700 roundtrip. Nevertheless, I had a 30% discount code that I had received as a result of my botched travels on Air Canada earlier this year, bringing the total down to around $500.

The cash flights would also give me an ideal schedule, whereas the only award flights with space available had me leaving Portland at 7am and arriving in Toronto at 1am, courtesy of an awkward 8-hour layover in Calgary – ugh! 

Moreover, once I factored in the taxes and fees I’d have to pay on an Aeroplan redemption (there’s lots of those, much to the frustration of Canadian travellers), I was looking at a value of about 1.45cpp on my redemption, which is not ideal at all.

Looking at the big picture, I knew that I’d be able to put the miles to a much better use on future trips, and so I decided to pay cash for the flights outright. In my mind, a $500 roundtrip is pretty reasonable for transcontinental flights out of Toronto to the Pacific Northwest, and I didn’t know when I’d otherwise be able to put that 30% discount to work, so it was a good time to use it up.

My overall routing looks as follows, all on Air Canada:

  • Toronto to Vancouver, departing 10am and arriving 12:02pm

  • Vancouver to Portland, departing 1:35pm and arriving 2:47pm

  • Portland to Calgary, departing 12:20pm and arriving 3:11pm

  • Calgary to Toronto, departing 5:10pm and arriving 10:51pm


As I mentioned, though, the question of redeeming miles vs. paying cash on North American flights often has no clear-cut answer, so make sure you carefully consider your options – in fact, sometimes it can even be a good deal to use cash in one direction and points in the other!

The decision can vary from person to person as well – in this situation, I came to the conclusion that paying cash was better, but someone else in the same position might choose to burn their points instead (for example, if they weren’t planning any future trips and were focused on paying as little out-of-pocket as possible).

The Hotel

It’s taking me a while to get used to the new Marriott hotel categories, because compared to the couple of years preceding the Marriott/Starwood merger, things have certainly gotten less favourable for those of us looking to score free nights using our points.

There’s usually a handful of mid-tier hotels under the Marriott, Renaissance, or Autograph Collection brands in every major city in North America. These hotels typically offer comfortable surroundings and a decent lounge and breakfast, making them my preferred choice for city breaks like this. Since they’re usually located centrally in major cities, though, they tended to fall into the higher-end hotel categories, with the very highest categories being reserved for top-tier luxury brands like JW Marriotts. 

The thing is, prior to August of this year, these higher-end categories were something like the Old Category 7 or even the Old Category 8, costing up to 40,000 points per night. Now, these hotels mostly find themselves within New Category 6, meaning that a free night goes for 50,000 points per night! That’s very hard to justify when the cash prices on these hotels typically hover between US$200 and US$300.

The situation in Portland was as follows. There’s two Marriotts – one by the waterfront and one in the downtown core. Then there’s the Hi-Lo Hotel, part of the Autograph Collection, and The Nines, part of the Luxury Collection, which both looked like serviceable hotels with plenty of character. All were Category 6, and all had cash prices of about US$250 a night for my four-night stay.

In the end, I picked the Portland Marriott Downtown Waterfront, both because it looked the newest and also because its cash rate varied throughout my stay, meaning that the first two nights were going for around US$350 and the last two for around US$200. I therefore redeemed 100,000 Marriott points for the first two nights – right on the cusp of what I’d consider an acceptable value for Marriott points – and paid cash for the remaining.

Portland Marriott Downtown Waterfront

Portland Marriott Downtown Waterfront

My total out-of-pocket spending for the trip, per person, was as below. It’s more cash than I’d normally spend on a trip like this, but then again you have to remember that the power of Miles & Points tends to be at its greatest when you’re booking a complex trip, and it can be optimal to pay for the simple weekend getaways with cash if you can put your points to better use on other trips.

  • YYZ–YVR–PDX–YYC–YYZ, Air Canada economy class with 30% discount: $520

  • Portland Marriott Downtown Waterfront, 2 nights: $264

  • Total: $784


After a summer of frenzied globetrotting, a relaxing long weekend on the West Coast is exactly what we needed, and I’m looking forward to renting bicycles, conquering hiking trails, and sampling some craft beer in the effortlessly hip (and gorgeously nicknamed) City of Roses. I’m sure plenty of readers – especially those living out west – have been to Portland, so please do send me all your recommendations in the comments below!

  1. Anna

    Hey Ricky, hope you and Jessica had a fantastic time in Portland! Any restos you recommend … and did you check out House Spirits Distillery via Priority Pass at the airport?

    1. Ricky YVR

      We followed some of Colin’s recommendations – loved the wings at Pok Pok and the food truck corner around the Target downtown. The donuts at Blue Star was incredible as well.

      Just finished up at Capers Market, the Priority Pass restaurant in Terminal D, where Air Canada flies out from, and we got a free US$112 in total to spend on food and goodies! (2 Priority Passes each with 1 passenger + 1 guest) Doesn’t get much better than that 🙂

  2. Atom

    Voodoo Donuts is pretty popular for fancy donuts… some say there are better places… but that’s probably because Voodoo has become so famous. Also, if you’re into the pub-crawl scene… they have these 12-person bikes which enable you to go from pub to pub legally… the DD steers and the pub-crawlers all do the pedalling… so it’s all kept legal.

    Depending on which day you go, there’s a good market in Portland… can’t remember where it is… and there’s this epic used book store in the city called Powell’s if you’re into rare books.

    1. Ricky YVR

      We saw the lineup at Voodoo and opted to head to Blue Star instead, but it certainly looked very busy on the inside. We also saw more than one passenger departing PDX bringing boxes of Voodoo donuts with them, so it must be quite a treat!

      The Portland Saturday Market and Powell’s Old Books were both very enjoyable as well. We got lost in Powell’s for quite a bit, but it was time well spent.

  3. Randall

    The Nines was one of my worst luxury hotel experiences ever! Glad you avoided it.

    1. Ricky YVR

      I’m curious what your experience was like? We thought the Marriott on the Waterfront was decent but that one of the downtown options might’ve been better, so I’d be interested to find out what you thought of The Nines for next time.

  4. Colin

    Amazing food in Portland! Grassa, Pok Pok, Screen Door, food trucks, skip Voodoo Donuts and go for Blue Star instead.

    1. Ricky YVR

      Invaluable suggestions, Colin – thanks so much. We loved the wings at Pok Pok!

  5. Jian

    But if you go to the Rip City, I suggest Moda Center.

  6. Jian

    Oh, my god! You booked again…

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