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How to get a vacation for ‘free’

Dan Bobkoff Feb 8, 2013

How to get a vacation for ‘free’

Dan Bobkoff Feb 8, 2013

A few months ago, I wanted to go to Japan, but I had a problem. Japan is one of the most expensive countries for an American tourist, and I had the budget of someone who works in public radio. A plane ticket is $1,300 in coach. A regular coffee there goes for as much as $6. And, hotels are something like $300 a night.  

So, I embarked on an adventure to see just how much of this trip I could get for free, courtesy of the big banks and airlines. And, I found I’m one of many playing this game. 

“They’re willing to try almost anything to maximize points, miles, or cash back from their rewards cards,” says John Ulzheimer of SmartCredit.com. He’s describing people like me: extreme point-hoarders, mile fiends. 

This trip to Japan could easily have cost $6,000 or more. But all told, for 17 days and four regions, I probably spent about $2,000, much of that food and a rail pass.  

I started by following the advice of Brian Kelly. He calls himself the Points Guy, and runs a website of the same name.  

“Essentially, it’s like collecting money. Miles and points are money. If you’re not taking advantage of them, it’s like throwing a wad of cash in the trash can,” Kelly says. For this trip, I needed every mile and point I could hoard. And, I didn’t actually have to travel to rack up. I signed up for credit cards with big bonus offers. One card scored me 100,000 airline miles. On another, spending $3,000 netted 50,000 points. These bonuses alone paid for most of the travel.  

What did it take to go on this trip?


British Airways Visa — 100,000 mile sign-up bonus
Chase Sapphire Preferred — 50,000 point sign-up bonus at the time
United MileagePlus Explorer — 25,000 miles, signed up when it was Continental Airlines
Chase Ink Bold — 50,000 point sign-up bonus

Chase has a number of cards that use the same rewards program, known as Ultimate Rewards. The points can be transferred and consolidated among accounts. Some cards, such as the Sapphire Preferred, allow you to convert those points into other rewards programs, such as Hyatt, Marriott, British Airways, United, Korean Air, and others. With a little research, it’s easy to find the best deals for redemption.


Direct Flight (New York to Tokyo) — 65,000 miles on United Airlines + $50 fees
-25,000 miles from United (then, Continental) credit card sign-up
-15,000 from actual flying
-20,000 transferred from Chase Ultimate Rewards

One night at Marriott Courtyard Ginza — 30,000 Marriott points (from actual stays)
Four nights at Hyatt Regency Tokyo — 24,000 Chase Ultimate Rewards Points converted into Hyatt points for two nights; two nights using British Airways Avios miles redeemed for hotel stay
Three nights at Hyatt Regency Kyoto — 18,000 x 3 = 54,000 Chase points converted into Hyatt Points
One night at Holiday Inn — Through British Airways Avios
Two nights at Mitsui Garden — Through British Airways Avios

To save money, Dan also stayed four nights at a nice hostel in Takayama. And, he paid for two other nights at traditional Japanese inns.

But this hobby can become obsession.   

“There’s one last term: the ‘are you freaking kidding me look.’ You’ll often get this from a spouse or partner,” Kelly said at one of his travel seminars. 

James Crawford knows that look. His fiancée at first didn’t get it. 

“She thought it was a little crazy that I was spending time on the phone with these banks,” Crawford says.

She came around when his points got them upgraded to business class on their trip to Japan.  

I just flew coach. Clearly, some people are beating me at this game. Crawford plans to pay for his honeymoon in Paris, Thailand, and Hong Kong with his points.  

Then again, he’s a former investment banker who programmed a spreadsheet to maximize his rewards. 

“I have a model where I can put in the distance of the flight and then also put in what credit card I’m using, and each credit card has different bonuses. I then input what my value is for the points that I’m earning for an AmEx point or a Chase point,” Crawford explains.  

There’s a lot of strategy here. For example, it takes far fewer Chase points to stay at a Hyatt than a comparable Marriott. 

Some point-chasers collect their big sign-up bonus and then cancel their credit card before the annual fee. 

John Ulzheimer of SmartCredit.com worries some will get into trouble with these games. Spending too much, racking up debt, or damaging their credit scores. 

“If you are constantly opening new cards just because you like the sound of the newest, hottest rewards program, then the damage you’re doing to your credit is pretty perpetual,” Ulzheimer says.   

That’s because every new application dings your credit score. And, credit agencies take into consideration the average age of your accounts, so many new ones hurts that.

But Brian Kelly, the Points Guy, says it hasn’t hurt him. He has 20 active credit cards. 

“I usually get about six, seven, eight credit cards a year that bank me almost half a million [points],” he says.  

So, how did I do on my trip? Kelly says I get an A in points-spending because I made the trip happen the way I wanted.

I didn’t tell him about the guy I met in Tokyo who got so many bonus points signing up for credit cards and bank accounts, that he got himself an around-the-world ticket. He was off to St Petersburg next. I guess that guy won that round. 

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