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  • Writer's pictureLogan

Booked: A Canadian Fall

I love Canada and am proud to call it home. When looking at my historical flights, I noticed a distinct lack of Canadian adventures. Sure, I've been to Toronto, Calgary and I live in Vancouver, but Canada extends a lot more than that. It bothered me knowing how much I love this country, but I haven't even seen the start of it.

After returning from a wonderful three weeks abroad in South America and two international trips planned towards the end of the year, I wanted to stay closer to home and see the parts of Canada I hadn't seen yet. By taking full advantage of a flexible work from home policy, I'll be able to travel on the weekends, work during the week, and explore areas in my free time.

My fall season will see me visiting Whitehorse, Toronto, Winnipeg, and Yellowknife.

Whitehorse: Thanksgiving

Whitehorse has been on my list for a while - it's located only a short flight from my home, and the wilderness activities are second to none. The long weekend brings an opportunity to spend three full days in the northern territory, and I plan to take full advantage of my time there.


The "flag carrier" of Yukon is Air North. They're known for their friendly hospitality, and freshly baked chocolate chip cookies served to all classes of customers. I planned to fly round-trip with Air North, relying on a cheap fare promotion that saw round-trips price at around $400.

Still warm to the touch!

However, Air Canada was quick to react and heavily discounted their fares as well - offering business class one-ways for 14 thousand Aeroplan points and a negligible amount of taxes and fees. Ultimately, I had to go for the best of both worlds and fly Air Canada in business outbound, catching the late flight of the day landing just before midnight on Friday. I'll make the early afternoon Air North flight on Monday, which will have me at home, just in time for Thanksgiving dinner.


I knew hotels in Whitehorse would be limited, but I was pretty surprised. Admittedly, I have been all too used to just pulling up the Marriott or Hilton app and just booking the cheapest option, but there are no properties in Yukon.

Then Best Western came up. I remembered they have an excellent status match program, essentially matching their equivalent status to any other hotel program's with no catches. I submitted the online form and matched my Marriott Titanium to their top-tier BW Diamond Select membership level. From form submission to seeing the status reflected in my account took only 9 hours - now that's good customer service.

I quickly booked the three nights in the Best Western Gold Rush Inn with my newly minted Diamond Select status - I'm not expecting much, but I would love to see some status recognition - perhaps an upgrade to a larger room would be nice. Pairing this status with their current promotion of $20 in gift cards back each night, I think I'm in for an enjoyable stay.

Best Western Gold Rush Inn - A Whitehorse Experience


No trip to the territory is complete without a viewing of the Northern Lights. If the night is right and the "aurora cast" shows a good reading, anyone can see the aurora borealis from anywhere in the province. Despite this, I've elected to take a tour.

At $129, the tour promises to visit three locations to ensure the highest chance of viewing, offers transportation to and from the hotel, and accompanying snacks and drinks. As my trip centers around seeing the Northern Lights, I will happily pay extra money for the highest possible chance of viewing.

Toronto: October 16 - 31

I've meant to get back out to Toronto for a while now. I'd love to see some friends I haven't seen in many months, and my company has an office there, allowing me some space to work from and meet other colleagues.


Flights are more of the same. I've flown Vancouver to Toronto on Air Canada in business class at least a dozen round-trip times, and this will be no different. I was able to snag fares before the October 1 deadline, which allowed me free cancellation and changes for all Aeroplan reward tickets. I paid just over 22 thousand Aeroplan for the outbound flight, booking into award business. I was unable to get a return flight due to AC's dynamic pricing woes and had to select a latitude reward fare instead, apply four eUpgrades, and instantly confirm an upgrade to business. With my eUpgrades expiring at the end of the year, I happily used them and saved approximately 30 thousand Aeroplan points.

Hope they have more of this mouth watering chocolate desert


I've found that Toronto hotel prices are either low or oddly expensive. I've never been to Toronto, when the prices are what I would call "fair". Needing to burn some of my Marriott Bonvoy points, I will stay in the St. Regis Toronto for five nights on points. The member-exclusive "fifth night free" will come in handy here, as I'm paying 240 thousand Marriott for this and want as much return as possible.

Caroline Astor Suite at the STR Toronto

I've heard mixed reviews about this property. I'm concerned with the butler service, and how unlike other St. Regis properties around the world, their coffee and tea service ends in the morning and isn't available 24/7.

On the other hand, I've heard this property is excellent with elite recognition - which is the only reason why I selected this over the similarly priced Ritz Carlton. Friends have received no-questions-asked upgrades to grand deluxe suites, and the two-bedroom residence is even available as an option for suite night awards.

Louix Louis Restaurant in the STR Toronto

I will not be applying my SNAs here. Instead, I hope to snag a complimentary upgrade a couple of days in advance over the phone and the in-app chat feature.


I'll likely be moving to Toronto permanently in the spring of next year, and I want this trip to be a "taster" of the city. While I've been to Toronto many times, frequently passing through on my way to school, I never stayed for more than one night.

Accordingly, I want to treat this city as my home - going to the office, working, enjoying dinners, and meeting friends. It's a short trip, but I'm sure I'll be able to maximize my time here.

Additionally, I have my $175 dining credit from American Express I need to spend. After visiting many restaurants on the Vancouver list, I am hoping to try something new in Toronto. Buca and Alobar are top of the list.

Winnipeg: November 3 - 7

The amount of people that said "don't go to Winnipeg" makes me want to go more. I can't take their word for it and have to see it for myself. I've never been to the "real" prairies (not counting Calgary here), so this will be a first for me. Yes, I'm going at a terrible time - namely, the weather will be hitting -10 degrees, but I still think it will be good to see.


Part of the reason why I'm doing Winnipeg is that the flights were so cheap. I paid exactly 3.3 thousand Aeroplan each way. For a three-hour round trip flight for only 6 thousand and about $60 in taxes and fees, it's tough to say no.

I'll be flying Air Canada and am considering a bid upgrade to business class. Both legs are on the 737 Max 8, a business class I frequently fly, but I will appreciate the comfort on a three-hour return.


As the only centrally located Marriott hotel, the Delta Hotel Winnipeg will be mine for the four nights. Located 10 minutes from Portage and Main, the hotel boasts a comfortable stay and a rooftop pool - I hope it's heated. As I only need the hotel for four nights, I can't take advantage of the fifth night free. However, I still booked for five nights - at the cost of only 65K Marriott points - and intend to checkout with mobile checkout to earn credit for the additional night. As a Titanium member with no hopes of hitting Ambassador, the extra night will offer no use, but this game is all about maximizing points, even if it makes no sense, isn't it?


As I'll be working in Winnipeg during my time here, I will have minimal time for other activities. An early morning returning flight on Sunday only gives me Saturday to truly explore the city.

Due to the cold, I think my time in Winnipeg will be one that visits many museums. The Canadian Museum for Human Rights has always been an interest of mine due to its prominence on the special ten-dollar bill, and I can't leave without visiting the Winnipeg Railway Museum.

I will be scouring the internet for cheap tickets to Friday's Winnipeg Jets vs. Chicago Blackhawks game. If anything, my time in Winnipeg will give me a break from Vancouver and help me explore more of our country.

Yellowknife: November 10 - 14

Second to Whitehorse in interestingness is Yellowknife. Currently, no travelers are allowed in the Northwest Territories unless you meet specific criteria, something I'm sure my tourism would not fall under. Accordingly, I'm more hesitant and haven't done much planning as I don't think this trip will happen, but I'm hoping it will.

Interestingly, Yellowknife is much more "spread out" than Whitehorse - something I've heard makes it seem larger, despite its smaller size. Yellowknife is my backup if the Northern lights aren't strong in Whitehorse; the lights are much more intense in Yellowknife due to its geographical area.

The Northern Lights from NWT -

This trip remains fully cancellable as I booked the ticket before the October 1 deadline. Due to current restrictions, I have not done much in the way of planning. I have hope that the NWT will open up, but it's not looking promising.


Before two more extensive international trips approach, I want to explore this beautiful country I am lucky to call home.

I don't think there is a better time to explore Canada than now. With Covid still limiting international tourism and many people on flexible work from home policies, the ability to see our home country has never been higher. It's time we see it, and I'm excited to start with these four cities!

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