The right way, and the wrong way, to redeem your travel rewards

For the average person flying coach from Italy to New York, the highlight of the nine-hour flight in a cramped airplane seat might be a hot meal or a good movie to pass the time.

But when Brian Kelly flew home to New York from Milan at the end of a two-week European vacation this summer, he had a bed, a shower and bottle of Dom Pérignon. The first-class flight on Emirates would typically cost about $5,000, but using travel miles, Kelly paid less than half that amount.

Kelly's self-described obsession with rewards programs began when he was a kid finding ways to use his father's miles so that their family of six could fly cheaply to the Caribbean every year. It grew during his 20s when landed a recruiting job on Wall Street, traveling the country and raking in a million miles a year.

Now, making travel miles go a long way - literally - is Kelly's full-time job. On ThePointsGuy.com, he analyzes rewards programs, alerts readers to sales and shares strategies for earning as many points as possible.

He recently spoke with The Washington Post about his travels - he says that he's now been to more than 60 countries - and the right way for people to earn and redeem rewards points. This interview was edited for length and clarity.

Q. When did you realize you could make finding travel deals your full-time job?

A. In 2007 I got a job on Wall Street doing all of the recruiting for high-tech computer grads. I was traveling a ton and then also running information sessions at universities. I was putting it all on my corporate card and raking in more than a million miles a year. And even though in 2008, 2009 working for a bank wasn't the best place to be - you know layoffs and everything, salary freezes - I was still traveling the world like a multimillionaire, and all of my friends truly thought I had a trust fund.

After telling people a million times it's all about the points, my ex at the time was like "Oh enough, why don't you start blogging and telling people?" So in 2010 I had my first blog post. I realized almost everyone has points and no one knows how to use them. A year after my first blog post I quit my job. The site started to grow exponentially and advertising dollars started to come in, so I decided to pursue full-time.

Q. Is it harder to earn miles now that you're traveling on your own dime?

A. I'm actually raking in more miles than ever, especially since I also travel a ton. So yes, it's coming out of my own pocket but there are more ways than ever to earn points and so many credit cards out there that offer [points]. I actually have an Amex card that I'm getting triple points on, on all my Facebook [advertising] spending. I have 23 different credit cards, but because I pay them off on time, am vigilant and have never had a late payment, the miles and points are raining from the sky.

Q. What do you say to people who are worried about opening so many credit cards?

A. If you're mired in credit card debt, do not, I repeat do not open up new cards because the interest rate is going to be higher than any of the points you get. If you're in debt, you can absolutely still get in this game, but I would first and foremost bring your debt down.

But for people who can manage their monthly finances, instead of paying cash, just put it all on a credit card and pay it off every month. You're getting free miles, which is basically free money ... Also, [you could try to find] programs [that] allow you to earn into a central pool and then transfer to different partners. You want to have a card that gives you a good signup bonus and also transfers to a lot of different partners.

Q. Is it better to earn cash back or miles when it comes to travel?

A. You need to view miles and points as currency and take into account how much you're earning for every purchase. For the sake of it, you're earning one airline mile per every dollar spent on a credit card. There are several cards that pay you 2 percent cash back for every dollar you spend. So for every $100,000 you spend, you could be getting $2,000 cash back from a credit card.

If you're not getting at least that in value from your airline miles you should just switch to cash back. And what I mean by that is if you travel domestically and you're spending 50,000 miles for a $400 ticket you would be better off just getting cash back and then not even dealing with miles so you could just use that cash back to purchase whatever flight you want.

Q. What are some other ways to earn miles that people might not know about?

A. You can actually shop through airline shopping portals. That means instead of going to Target.com, Nordstrom.com, never, never never go directly through those websites. Always click through a mileage portal. All the major airlines and hotels have these shopping portals where you actually get extra miles just for clicking through the portal. There's a website, evreward.com, which actually lists all the shopping portals and how many miles per dollar you can get. And this is in addition to using a credit card that earns miles. This is kind of like double dipping. You could use a Delta card and shop through an American Airlines Nordstrom site and then you'll earn American and Delta miles. It's unbelievable. It's a no brainer.

Q. What is the best way to spend your miles so that you get the most value?

A. Generally, I redeem miles for super expensive, international, first- and business-class flights. It's like buy low, sell high. You try to get the miles as cheaply as possible and then you try to redeem them for as much as possible.

Q. Is it sometimes better to stock up on miles? To redeem, say 90,000, on one trip instead of three?

A. I would put together a plan and goal. So pick your destination. Where do you really want to use your miles to go and then work your way back from there. See what frequent flier programs are the best. Do a little bit of research and then work your way back from there instead.

It's thinking holistically. When you have a goal in mind it's easier to put a plan in place. I know people get overwhelmed because they have miles in a million different accounts. It's definitely good to have that goal.

Q. What catches should people watch out for when they redeem their miles?

A. When you redeem miles, for the most part, you can't upgrade. So sometimes it makes sense to pay for an economy class ticket and then use miles to upgrade. But always, always, always triple check with the airline if the fare is upgradable. Don't just buy it online and assume [you'll be able to upgrade] because the airlines may have changed the rules lately.

Q. Does it make sense to focus on earning miles with one airline?

A. There's a lot of different factors. Even if you fly one airline a lot you don't have to double down and then also get that airline's credit card. A real tip is to diversify. You don't want to overexpose yourself to one currency because the airlines do change the programs all the time. They change the rules, they increase the amount of miles. There's blackout dates sometimes. You don't want to have everything in one program because you don't have as many options when it comes time to redeem.

Q. Are there times that it makes sense for people to save their points and just pay for the flight?

A. I just got back from Africa and I flew from Cape Town to Doha, Doha to New York. It was $1,800 in business class but I paid for it because it got me 20,000 miles, which I value at like $400. Plus it got me 10 percent of the way to elite status notification. So I paid for it, accrued a ton of miles, got closer to elite status, and it was really comfortable. When there's business-class sales and other deals I'll totally pay for flights.

Q. How many miles do you have now?

A. I have probably more than 5 million miles. And I use my miles. For my parents' wedding anniversary I helped them get to Hawaii. I do a lot of charity work and for charity I use my miles. My tip is don't hoard them because they do go down in value [when airlines change their rules for redeeming them].

Q. How often are you on a plane?

A. I am usually traveling domestically once a week and then internationally once a month.