Travel hackers beat the system

Intense frequent flyers use tricks and loopholes to maximize rewards and see the world for free

Using a simple trick with his loyalty card and the United States Mint, author Chris Guillebeau earned enough air miles to fly to Europe, in business class, without spending a penny.

For about 18 months, it was possible to buy U.S. dollar coins directly from the Mint, which included free shipping.

Over the course of a few months, Guillebeau bought $70,000 in coins using a points-collecting credit card and then re-deposited the coins in the bank to pay his bill.

“Banks weren’t thrilled about all these arrivals of single-dollar coins in large numbers,” chuckles the American author.

But he earned 70,000 air miles through the trick, which he used to fly to Europe for free.

Guillebeau is a travel hacker, an extreme frequent flyer who racks up thousands of points and countless free flights.

Travel hackers are committed to beating the points system by maximizing their rewards while spending the least amount possible, finding loopholes and exchanging strategies to travel the world on a budget.

Guillebeau has racked up more than 1 million points per year for the past three years. He’s been an active traveller for more than 10 years, visiting 185 countries.

“Many of these trips have been free or almost-free, thanks to travel hacking,” he explains in an email. “I can safely estimate that I’ve made it to at least 50 of the 185 countries on award tickets.”

Those free trips include traditional vacation destinations such as Barbados, but also many unconventional locations, such as a trip to Iraq.

Guillebeau’s secret to earning points travel? Paying attention and spending strategically.

But Matthew Bailey, who runs the travel hacker website Canadian Free Flyers, emphasizes the importance of spending responsibly when using credit cards.

“Don’t hold a balance because paying interest defeats the purpose of travel hacking,” he says via Skype from Laos. “And don’t spend money on just anything; buy things you need.”

Bailey’s website promises to teach subscribers how to earn 80,000 Aeroplan points without setting foot on a plane.

He’s so confident in his advice, he even guarantees his members will earn at least one free flight after signing up.

An avid traveller, his greatest points coup has been flying to Mexico for free with his fiancée.

Bailey was inspired to start travel hacking after reading through Guillebeau’s website, The Art of NonConformity. He eventually started his own group when he realized much of the advice offered on Guillebeau’s site applies only to Americans.

“I had Aeroplan points for a long time and I never earned anything,” he says.

Bailey wanted to start maximizing the number of points he was earning on a regular basis.

He started by looking for credit cards that offered large points bonuses for signing up. Often companies would waive the card’s annual fee for the first year. This would give Bailey an opportunity to collect bonus points without paying for them.

“What I would do would be to apply for the card, wait a few months and then cancel the card,” he says. Sometimes, he would even be able to re-apply for the card and earn the promotional bonus points again.

Bailey also recommends reading your credit card agreement to see if you can transfer your points to Aeroplan without losing a lot in the process. If you can’t transfer your points, or you don’t think you’ll use the ones offered by your card, it’s probably not worth collecting them, he says.

To earn extra points, Bailey also watches for promotions.

Recently Sobeys and Aeroplan offered customers a free flight if they made 35 transactions in a month. By examining the fine print of the promotion, Bailey discovered that transactions could be for as little as $3. He made 35 small purchases throughout the month to earn his flight.

That’s the real secret of travel hackers: finding ways to make impossible points goals possible.

Bailey’s best advice for anyone who wants to start seriously collecting travel miles?

“Even if promotions seem like they’re out of your league, think in creative ways to see if you can get the points.”