Creating a Travel Hacking Strategy

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When it comes down to it, travel hacking is very straightforward. You apply for credit cards, collect the sign-up bonuses, and then you use those points for “free” travel. The thing is, you still need to have some travel goals in mind before you start travel hacking. Applying for a bunch of credit cards just because the welcome offer is good isn’t the best strategy. You need a travel a travel hacking strategy.

Generally speaking, you want to have 2 – 3 travel goals in mind. One short-term, and one long-term goal is the easiest way to start. It’s also a good idea to have one redemption in mind that would be nice to have, but not a huge deal if you never obtain it. 

You need to have these goals in mind because they will dictate what credit cards you apply for and at what pace. The goals will also keep you on track because every point or mile you earn is one step closer to your free trip. Here are a few different goals and how you would obtain them.

Flying across Canada in economy for free

Let’s be real for a second. Travel hacking is not for everyone. A lot of people don’t like the idea of applying for multiple credit cards and find redeeming flights difficult. However, with the recent changes to Aeroplan, getting a free flight has never been easier. 

Let’s say you want to fly round-trip from Toronto to Vancouver sometime in the next two years. This is your short-term goal, so you should plan your travel hacking strategy accordingly. According to the Aeroplan rewards chart, it’ll cost you between 12,500 – 17,500 points each way for an economy flight. That’s a good estimate, but you also want to check your exact dates to see how many points it’ll take to get your flight. 

I randomly chose April 2 – 9, 2022 as the travel dates. This is a Saturday – Saturday trip, which is common for many people. Here’s how many Aeroplan points it’ll take you to get a free flight (remember, points are calculated per direction).

Creating a Travel Hacking Strategy YYZ

As you can see, for the YYZ – YVR segment, most flights require 17,500 points. However, the 8 AM flight only takes 11,200 points which is a huge savings. Premium economy is also a decent value since it’s only 1,200 points more than economy for the 7:15 AM departure.

Creating a Travel Hacking Strategy YVR

Most of the return flights also require 17,500 points. That means for these dates, you’re looking at 35,000 Aeroplan points + $76.25 in taxes/fees. That falls exactly in the upper estimated range. However, you’ll also notice that there is a return flight option for 11,200 points. If you booked both of the cheaper options, it would only cost you 22,400 points + $76.25. That’s a savings of 12,600 points. If you can make the times work, it would be worth it.

The key thing to understand is that you can potentially get a return flight from Toronto to Vancouver for 22,400 Aeroplan points + $76.25. All of the best Aeroplan credit cards in Canada have welcome bonuses that are worth well more than that. Heck, depending on the current welcome bonus, you could get enough points for two round-trip flights with the American Express Gold Rewards Card or the TD Aeroplan Visa Infinite Card. If you went the premium route and signed up for the American Express Platinum Card or the American Express Aeroplan Reserve Card, you’d have enough points for four round-trip tickets. 

One credit card sign-up bonus could earn you up to four roundtrip flights within Canada. Travel hacking doesn’t seem so difficult anymore, right?

Overwater bungalows in the Maldives

Many people dream about staying at an overwater bungalow in the Maldives. Unfortunately, since the nightly cost of these stays is at least US $1,000 a night, it remains just a dream. However, if you collect enough Marriott Bonvoy points, you can guarantee yourself a stay for free (plus resort fees, of course). You just need to set up that travel hacking strategy.

For example, the JW Marriott Maldives Resort & Spa allows you to book an overwater bungalow for 85,000 Marriott Bonvoy points during standard times, or 100,000 points during peak times. Since Marriott Bonvoy gives you the 5th night free when booking 4-nights, it’ll cost you as little as 340,000 points for five free nights. 

Okay, 340,000 points is not a little. In fact, it’s A LOT. It’s highly unlikely you’ll be able to save up that many points in a year or two, so you need to think of it as your long-term goal. Maybe you have a special anniversary coming up, or perhaps you’d like to during your honeymoon. Since you know you’ll need at least 340,000 Marriott Bonvoy points, you can plan accordingly. For example, you could do the following:

Since you can transfer your American Express Membership Rewards Points to Marriott Bonvoy at a 1:1.2 ratio, you can actually get 340,000 points relatively quickly. You would need to sign up for at least four credit cards. Two of them being business cards since they give you an incredible sign-up offer. Also note that Marriott Bonvoy is eliminating the rewards chart and going full dynamic in March 2022. That means the cost of these bugalows will be less predictable.

While this may seem excessive, if you’re only applying for one new card a year, it’s not really a big deal. Remember, you’d also be cancelling your old card each year, so overall, you’d only be managing 1-2 cards a year.

Figure out what programs will help you reach your goals

As I mentioned in a previous instalment of this series, there are only a few major travel rewards programs that you need to be familiar with:

Regardless of your goals, you need to figure out what programs will help you reach them. In my short-term example, you’d have to focus on collecting Aeroplan points. With the overwater bungalows, the priority needs to be Marriott Bonvoy.

Now let’s say you have a very specific redemption in mind. For example, a couple of years ago, I flew first class on Emirates. At the time, I knew I could redeem 150,000 Alaska Miles for a one-way journey between Dubai and Toronto. I considered this a redemption that would be nice to have, but I wouldn’t be upset if it didn’t happen.

Admittedly, earning 150,000 Alaska Miles was not easy. There are only two credit cards in Canada that allow you to earn Alaska Miles directly. That said, I knew I could also transfer Marriott Bonvoy points to Alaska Miles at a 3:1 ratio. Not the best ratio, but it was another option available.

The point is, you need to figure out your goal first, so then you can come up with the right travel hacking strategy. That said, even if you’re the type that doesn’t plan out super far ahead, you could focus just on American Express Membership Rewards and Aeroplan since they give you the most flexibility. If you’re going for a niche redemption, then you’ll want to plan out as far as possible.

Get the right credit cards

If you read my chapter on how to travel hack, you’ll know that I’m a big advocate of the two credit card method. As a quick refresher, you’d have one primary card, and then you’d get one new one every year. Your short-term and long-term goals would dictate what cards to get.

For example, if you know you need to focus on Aeroplan, then having a card that earns you Aeroplan points is what you’d want for your primary card. I personally recommend the American Express Cobalt Card. Although the sign-up offer takes a year to get, it has a high earn rate which makes it an ideal primary card. You would then apply for any additional card that helps you reach your goal each year.

American Express Cobalt Card

  • $12.99 Monthly fee ($155.88 yearly)
  • 2,500 monthly Membership Rewards points after charging $500 in purchases each month for a year (30,000 points total)
  • 20,000 additional points when you spend $3,000 in the first three months
  • Earn 5 points per $1 spent on eats and drinks
  • Earn 3 points per $1 spent on streaming services
  • Earn 2 points per $1 spent on travel
  • Earn 1 point per $1 spent on all other purchases

The key thing to understand is that the welcome offers available can change at any given time. It’s always worth monitoring them to see what’s available. For example, both the American Express Cobalt Card and the American Express Gold Rewards Card typically have a welcome bonus of 30,000 points. However, there are often promos where the offer is 50,000 points. Obviously, that’s a better deal, so you would want to prioritize your goals.

You should have a rough idea of what card you’re going to apply for next. That way, if there is a good promotion, you could just apply for it right away. Otherwise, just stick to getting one new card a year if you want to be a lazy travel hacker.

By having travel goals in mind, you can easily plan out your travel hacking strategy. Some redemptions will only require a sign-up. However, if you’re playing the long game, it’ll take many years and multiple credit cards. That’s why you need to always have a plan in place.

Travel Hacking for Lazy People

Creating a Travel Hacking Strategy

About Barry Choi

Barry Choi is a Toronto-based personal finance and travel expert who frequently makes media appearances. His blog Money We Have is one of Canada’s most trusted sources when it comes to money and travel. You can find him on Twitter:@barrychoi

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