My Miles & Points Journey: A Complete Timeline [2020]

I first wrote this post in the summer of 2018 to document my Miles & Points journey, year by year. I thought I’d give everyone an update for the rest of 2018, 2019, and the first half of 2020 – scroll down to the “2018” section to pick up from where we last left off. I’ll also look to continue updating this post biennially going forward.

Earlier this week, I was doing that thing I always do when flying in a premium cabin: setting aside my glass of bubbly, reclining my seat all the way back, sprawling out on the flat bed, and thinking to myself, “What sort of bizarro world do we live in where all of this is possible?!”

After all, I had paid barely $70 out-of-pocket for this flight, one which usually retails for thousands of dollars, and that’s merely the example at hand. Loyal readers will know that I’ve been travelling pretty much nonstop in the past few months, redeeming hundreds of thousands of points in various mileage currencies and scoring my airfare and accommodations at similarly jaw-dropping discounts. 

Of course, this requires earning those miles to begin with, whether that’s through credit card signup bonuses, referrals, or simply buying miles outright. These days, I have pretty healthy balances in all my mileage accounts, but things weren’t always this way – not too long ago, I was not only scraping together 30,000 miles to book a “free” one-way economy ticket to Europe, but also feeling pretty damn satisfied with myself for it!

I’ve come a long way since those days, and in this post, I wanted to dust off the history books and talk about my journey from a beginner points collector to an advanced practitioner. 

One of the missions of Prince of Travel is to help every dedicated reader unlock the power of Miles & Points in order to be able to travel the world in a way that’s satisfying and fulfilling to them. It’s my hope that reading about my experiences will allow you to replicate my successes, sidestep my mistakes, and visualize your own journey towards mastery of this art. I often tell people that “if I can do this, then anyone can”, and while that’s technically true, having a blueprint of what to expect along the Miles & Points journey makes it a much more meaningful statement.

2013: Wish Upon a Star Alliance Gold

June: I’ve told this story before – what got me started with Miles & Points was, in fact, an obsession with airline status. Back then, Aegean Airlines Miles+Bonus was offering an easy route to Star Alliance Gold, allowing you to earn top-tier status with the world’s largest airline alliance by accumulating just 19,000 elite miles.

Regularly flying between Canada and China on cheap economy fares at the time, I start crediting all my flights to Aegean, looking to secure Gold status by the end of the year. 


November: I’m basically duped into applying for my second-ever credit card. You see, MBNA offers a little-known line of credit cards that are associated with various universities’ alumni organizations, and I unwittingly get myself signed up for the UofT version when I drop by the booth when walking to class one day. I only find out that it was a credit card application a few weeks later, when I receive a shiny new piece of plastic to go in my wallet.


As it turns out, the MBNA card’s 1% cashback beats out the 0.5% I was getting on my introductory TD Rebate Rewards card, but I still keep using the TD one because I don’t know any better. Many years down the road, the UofT Alumni card would eventually be sacrificed in favour of multiple MBNA Alaskas

December: My Christmas flight back home to Beijing finally brings me up to the 19,000-mile threshold with Aegean, but unfortunately I arrive late for my return flight, thus delaying my maiden lounge visit for another six months. Still, I proudly show off my Gold card to my university roommates upon my return. They congratulate me on my smallest of victories, failing to recognize the sheer monster that’s being created right before their eyes.

2014: “Member Since”

March: Buoyed by my success with Star Alliance Gold, I start reading FlyerTalk a little more seriously. I notice lots of people talking about earning points via credit cards and slinging around jargon like “Mini-RTW in F”, but I fail to take action. Instead, I continue spending my time plotting out where I’m going to credit my revenue flights in order to scrape together enough miles for a “free” ticket.

May: I grace an airport lounge with my presence for the very first time, slipping into the Toronto lounge a few minutes before my flight to Hong Kong is about to board. That first bite of a stale Maple Leaf Lounge cookie? Heavenly.

June: I redeem around 25,000 Air China PhoenixMiles – basically all the miles I had accumulated since childhood – on my first-ever “First Class” experience of any kind, a domestic Air China flight from Shenzhen to Beijing in the front of the plane. After my first encounter with fine dining at 37,000 feet and being addressed as “Mr. Zhang”, a craving for more of the same slowly begins to take hold.

Air China domestic, my maiden First Class flight

Air China domestic, my maiden First Class flight

August: Preparing for my study abroad in London, I work out that I’m able to use the miles I’ve collected in Aegean Miles+Bonus and United MileagePlus towards a round-trip flight back to Toronto and a flight for Jessica to visit me next year, except I’m still short about 30,000 miles.

Lo and behold, the American Express AeroplanPlus Gold Card was offering an excellent bonus of 30,000 Aeroplan miles with a first-year fee waiver, so I jump on that. Since it’s my first Amex card, there are issues with verifying my identity, and I even go so far as visiting the American Express HQ in the Toronto suburbs to complete the process. 

The card doesn’t get delivered until after I leave Toronto, so Jessica has to drop by my old temporary housing spot and fish the envelope out of the trash. Was it worth it? You bet – the two of us are able to reunite quite a few times while I’m away, including a one-month backpacking trip in Europe in the spring of 2015. The magic of Miles & Points was on full display for the first time.

2015: Credit Cardio

February: By sheer accident, I stumble upon one of One Mile at a Time’s reviews of premium cabins, and find myself intrigued as to how this regular-looking guy, not much older than myself, can fly around the world in business class and First Class so often.

I finally realize that racking up the points via credit cards was the answer, and the idea of travelling the world by earning and redeeming points, while maximizing value on both sides, becomes crystal-clear in my mind. I immediately set out to put together a strategy for credit card applications upon returning to Toronto in the summer.

July: I hit the ground running with a trio of new credit cards: the TD Aeroplan Visa Infinite for 30,000 miles, the Amex Gold Rewards Card for 25,000 MR points, and the now-defunct Chase Marriott Visa for 50,000 Marriott Rewards points. I try to convince Jessica to do the same, but she flat-out refuses, to my utter dismay.


September: My first MBNA Alaska arrives, laying the groundwork for a dream flight in Cathay Pacific First Class. It’s also at this point that I begin to realize the importance of networking, so I exchange emails with bloggers and start participating in forums in order to build up my knowledge.

December: Mulling over potential New Year’s Resolutions, I briefly toy with the idea of writing a blog about my travels and my newfound Miles & Points undertaking. However, I can’t decide on a satisfying domain name to use, and the thought flitters away.

2016: Immersions, Excursions, and AC Conversions

April: I continue my credit card merry-go-round at full tilt, adding the Amex Business Gold Card, the Amex Platinum, and two more MBNA Alaska cards at three-month intervals. Shortly after my third Alaska arrives, MBNA changes their policy to forbid people from holding multiple Alaska cards at once, leaving my plans for a two-person First Class getaway in tatters. I also learn about product switching, thus allowing me to downgrade my TD Visa Infinite to a no-fee card, ready to be upgraded once again at a future date.

Amex Platinum Card.png

May: In planning my travels for the upcoming year, I resist the temptation to splash my newly-earned points on economy class flights, having learned that the true value lies in premium redemptions. Instead, I book a cheap fare to London and Lisbon for myself and Jessica in late summer, which comes to about US$200 all-in.

June: I dip my toes into the US credit cards market, applying for my ITIN successfully and nabbing the US-issued Amex Premier Rewards Gold Card via Global Transfer.

October: I attend the PointsU Conference for the first time, which opened my eyes to the active community of travellers and points enthusiasts around me and inspired me to take my game to an even higher level.

2017: Prince of Travel

February: Still unable to fend off my itch to write stuff about my travels, I conjure up the name “Prince of Travel” in a coffee shop and launch the website the very next day. Around the same time, I complete my first meaningful redemption of the points I’ve earned via credit cards: a five-night stay at the Marriott Resort St. Kitts during reading week. 

Over a beachside dinner one day, Jessica indicates that while she’s appreciative of our steeply-discounted vacation, she still thinks this whole points-collecting gig is just smoke and mirrors, with little in the way of tangible rewards at the end. I tell her that she ain’t seen nothing yet.

The Marriott Resort St. Kitts, my first major hotel redemption

The Marriott Resort St. Kitts, my first major hotel redemption

March: The AC Conversion Card begins its slow death, with Canadian Dollar loads being restricted to $100/day. Nevertheless, I’ve come away with hundreds of thousands of miles coupled with a stronger understanding of the principles of MS, and I begin looking for the next big opportunity around the corner. 

May: Finally, at long last, I put all the points I’ve earned to good use by flying around the world in 16 days in business class. Somewhere along the way, I turn towards Jessica in my neighbouring seat and ask her, “Now will you start applying for credit cards?”, and she nods reluctantly as she takes another sip of her champagne.

Brussels Airlines business class, my first long-haul premium class redemption

Brussels Airlines business class, my first long-haul premium class redemption

October: Lufthansa First Class, check! Meanwhile, traffic starts to pick up on Prince of Travel, and I begin taking it much more seriously. The credit cards and MS continue at their usual pace, but referral points from the blog begins to take over as my primary source of accumulating points. On the US side, I’m approved for my very first card with Chase – the Sapphire Preferred.


November: The Star Alliance Gold story comes full circle – after three years of maintaining my Gold status through back-breaking mileage runs, I finally do the sensible thing and allow it to lapse. I’m crestfallen when Aegean sends me a newly-minted Star Alliance Silver card, but take comfort in the fact that I can reliably enjoy the same benefits as before by flying in premium cabins these days. 

2018: What’s Next?

February: I knock off another few First Class experiences off my bucket list, flying on Japan Airlines, ANA, and Cathay Pacific within the span of a few months. My taste in caviar is coming along in leaps and bounds.

August: Blessed with a steady inflow of points thanks to referrals, MS, and new credit cards in both Canada and the US, my focus shifts to how I can best leverage my points to take the trips that I’ve always dreamed of taking. I kick off this exciting phase with a tour of Latin America and a journey along the Trans-Siberian Railway, and I can’t wait to see what other adventures lie ahead.

Written in July 2020

September: After completing my Trans-Siberian Railway journey and spending some time in Asia, I returned to Canada by way of a last-gasp flight on Asiana Airlines First Class shortly before the product was phased out. I also attend PointsU 2018, once again having a great time connecting with the community and this time even sharing a few tricks of my own.

2019: A Year of Amazing Travel

January: The year begins with a crazy Aeroplan Mini-RTW that brings me to Africa and Oceania for the first time, completing a traveller’s milestone of visiting all six continents and allowing me to sample the novel tastes of Ghanaian jollof, Australian flat whites, and both the 2004 Krug and the 2009 Dom Perignon onboard my first flight on Singapore Suites. The United Island Hopper, at the end of the journey, checks off one of the major bucket list items on an aviation geek’s list.

February: With the official launch of Marriott Bonvoy, I can’t help but feel like the value in hotel points from a Canadian perspective is on a worrying downward spiral compared to the heyday of Marriott Rewards and SPG from before. I adapt my strategy accordingly, opting to pay cash for hotels more often (while looking deeper into things like third-party booking services) and reserve my Bonvoy points for only the most special redemptions.

May: Speaking of special Bonvoy redemptions, how about Mystique Santorini and Al Maha Desert Resort Dubai, with a handful of other very memorable hotel stays sprinkled throughout on a month-long Middle East trip? The best sweet spot of 2019 was Marriott Bonvoy’s luxury hotel redemptions for only 60,000 points per night at the Category 7 rate, and I was on a mission to try out as many of these as possible throughout the year.

June: To cap off the trip? A 27-hour itinerary onboard Emirates First Class (old and new), thanks to an Alaska Mileage Plan sweet spot that still exists to this day (and is easier to book due to Emirates’s relaxed availability patterns on their New First Class, for anyone who wants to make a speculative booking for 2021).

Emirates 777 New First Class, my best flight(s) so far

July: A month-long trip to Japan, China, and Cambodia ranks as one of my favourites in recent years. Returning home, I focus on raising my US game a little bit, knocking out new applications for the Hilton Aspire Card, the US Platinum Card, and the Citi Premier Card – while also embarking on Rounds #4 or #5 of perennial favourites like the MBNA Alaska or the CIBC Aerogold for Business.

November: After spending a few months settling into Montreal following a summer move, I embark on another convoluted Mini-RTW journey to get my fill of flying around the world. As before, most of my cash is actually being spent on hotels and accommodations for the trip, and I find myself grappling with the fact I’ve spent far more actual dollars on travel this year than any previous year – but I’ve also gotten to realize far more of my travel dreams as well. While my journey may have started in 2013 with the allure of “free First Class flights”, I’ve come to realize that it’s instead more about supercharging your travel possibilities: the greater a travel budget you have to begin with, the greater the degree to which Miles & Points can act as leverage on that budget and stretch the value further.

2020: Will This Year Please End Already?

January: With Aeroplan removing the second stopover and facing an uncertain future, it’s time to explore a wider variety of award chart sweet spots. I kick off the year with a proof-of-concept of the Avios multi-carrier award, which allows me experience Japan Airlines First Class for the second time (although I would sadly have to cancel that multi-carrier award later in the year due to a pesky pandemic).

March: We’re all familiar with the events of the second week of March 2020, but I’ll always be grateful that we managed to return from a very special trip to the Maldives just before everything got a little crazy. Aside from all the fancy First Class flights, the overwater villas of the Maldives were probably one of my greatest motivations for getting started with Miles & Points back in the day, so it was an incredible experience to finally make that dream a reality seven years later (of course, getting engaged under the Maldivian sunset wasn’t bad either). 😉

JW Marriott Maldives, my first experience at an overwater villa resort

May: COVID-19 decimates the global travel industry and leaves long-lasting effects on the Canadian loyalty landscape as well. As we’ve seen recently, this period was all about playing in “defensive mode” as credit card issuers tightened their belts and signalled a heightened risk aversion. It was a time of taking advantage of the few outstanding offers that did arise (Travel at Home and Double Rewards, to name a few), making relatively few big moves otherwise, and recharging our batteries while waiting for the prospects of future travel to re-emerge. Besides crunching through a few $900+ Platinum Cards and earning lowly Prestige 25K status for the first time via Travel at Home, I’m pretty content to take things easy.

July: As spring turns into summer, Canadians’ appetite for travel seems to be on its way back, if only very gradually. I loosely plan a handful of domestic trips, taking advantage of the many good deals designed to tempt us back into travelling throughout the rest of the year. I also ramp up the credit card cycles again, switching my RBC Avion to the WestJet MasterCard and maybe throwing a few high-end TD and CIBC cards into the mix as well, as we look ahead towards a much-anticipated upturn in fortunes in the Canadian loyalty landscape in the latter half of this god-forsaken year. 


There you have it – a year-by-year timeline of how I went from signing up for credit cards on accident to enjoying frequent trips around in the world that I could’ve never imagined in my wildest dreams. Looking back at all these years of dabbling with Miles & Points, I think the biggest takeaway is that it’s all about simultaneously working on many fronts to achieve your goals. Credit cards, hustling for referrals, the US side of the game, maximizing redemptions, networking – each piece of the puzzle is important in its own right.

Ultimately, everyone goes at their own pace. It took me about five years to go from the initial spark of interest to a high-level understanding of things; it may take you less or more. And no matter where you are on the learning curve, make sure to savour the fruits of your labour when you redeem your points for trips – after all, it’s pretty crazy that all of this exists in the first place.

Let’s revisit this post in another two years’ time, shall we?

  1. SoyMexicano

    Just wanted to say a big thank you for all your leg work on this topic, and all the others I’ve read in he last few weeks!

    At 60, I just signed up for my first ever AMEX card (Gold charge card) today, and did so thru the referral link on your blog as a way to say thanks:). Did the free supplementary card for my wife and got the extra 5K points.

    Unfortunately signed up for my first ever Alaska World Elite two weeks ago (and my wife signed up for hers as well), before coming across your blog/videos, and learning about GCR…lessons learned:(

    Our goals are similar to your original one; that being flying up front (instead of in steerage), eating Caviar and sipping bubbly. We don’t have as much of a time horizon as you do, but your information will help us fast-track to the promised land.

    Next up – acquiring a US bank account, more AMEX (US) cards, and eventually meet the “Chase Family, Conrad Hilton, and Ms. Marriott Bonvoy”.

    Thanks again!

  2. Annie

    Hi Ricky,
    First of all, love your new website! I have been following you and read your blog for years, since there are not many travel/credit card blogs for Canadian market compares to US markets. To achieve all these perks, you have spent a tremendous amount of time and effort for sure. Looking forward to read about your next adventure!

  3. Vagabond YYC

    Ricky, what a great article of your game. I had to take notes…again, since I have been in that ‘flittering’ stage with too much on my plate overall in life. Thanks for such an interesting article…amazing where you started and where you right now. Well done!

  4. Terence Rebello

    Ricky, Always very happy to read your articles. I enjoy them. Hope I or rather we, me & my wife can accomplish 60 to 70 percent in terms of travel on points you do. Keep it up both sharing your knowledge, your encouragement and your travel. Best Wishes Terence Rebello

  5. Abubakar

    Always refreshing to reread your blog!

  6. Garry

    Articles like this are one of the many reasons this is one of the best blogs in this field

  7. Bernard

    Enjoyed reading this write up. Please consider updating it yearly.

  8. Alex S

    This is a great summary, thanks for posting!

    I’ve always been curious at how long it took you to earn your first redemptions, so this is great as it gives a baseline for myself.

  9. Daniel Jordan

    Ricky, I just have to say thank you. I stumbled upon your blog last November and after reading through just a few of your posts, the potential of all this finally sank in. Since then, I have travelled across Canada and Europe in luxury all on points. I tell everyone I run into to check your blog to see how to do the same. Thank you again, and I look forward to your next post.

  10. susan

    Thank you again for a great article. Look forward to more.

    Susan S. Calgary

  11. Rose Mary

    Hi Ricky,
    Great article. Any chance you could say a little more about your statement:

    Instead, I book a fuel-dump fare to London and Lisbon for myself and Jessica in late summer, which comes to about US$200 all-in.

    What is a fuel dump fare and how can I get a fare to London and Lisbon for US 200?

    1. Ricky YVR

      This merits its own article one day! Google “fuel dumping” for a few intro guides that have been posted around the web.

      While it sounds nice, in practice it takes a lot of work to accomplish – much more work than learning to maximize points, and in most cases for lesser rewards.

  12. Linda

    A terrific article – I really enjoyed reading it. I suspect everyone on this site has experienced that feeling of ‘you can do that?". LOL.
    And what is it with the relatives and friends who keep telling me it’s too ‘overwhelming’ and ‘too much work’ to collect points for free holidays and flights? Bizarre.

    1. Ricky YVR

      Consider me a “workaholic” then 😉

  13. andyin250

    Another incredible article. Very detailed and informative. I just started my journey recently thanks to your blog. What is your opinion on getting into the US market while I am still a newbie? Is the US market that much more attractive? I have read your article about how to obtain US CCs and all but still would like your opinion. I feel like I should master the Canadian territory first before I make that plunge. Always an inspiration Ricky 😉

    1. Ricky YVR

      In the long run, getting into US credit cards allows you to earn points much faster (since there are so many cards with good offers) and opens the doors to a much wider variety of redemptions. But it does involve a considerable amount of time and effort to get started.

      Ultimately, your resources in terms of time/effort are finite, so I do think it’s a good idea to get comfortable with the Canadian side of the game before getting into US cards.

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