Extra nights in cushy hotel suites, free premium air travel and even stays on private islands. Loyalty points and frequent flier miles, when strategically collected, can fund trips well beyond a traveler’s usual expectations and budget.
But it isn’t easy to get these deals. Luckily for us, there’s an entire universe of experts who share their savvy in booking award travel, and at the forefront is Brian Kelly, who founded the travel website The Points Guy in 2010.
For Mr. Kelly, 41, it started with the childhood challenge of booking travel for his family. At 12, he planned an entire vacation to Grand Cayman for his family of six, booking all of the flights with miles earned by his father. This successful trip laid the groundwork for his career as travel expert, he said. Deals still dictate his travel.
In his new book, “How to Win at Travel,” Mr. Kelly shares advice on everything from understanding points and miles to handling flight disruptions and flight anxiety.
He shared some of that advice with The Times, discussing how to strategize purchases with credit cards (he has 29!), flying with children in business class and the evolving world of award travel.
This conversation has been edited and condensed for clarity.
You’ve researched points and miles for decades. What’s still fun about it?
I love solving the puzzle. Yes, it’s a little bit difficult, but that’s also the point. If it was so easy for everyone in the world to use, it wouldn’t exist. For those who want to put in a little bit of work, I think there’s still a really high reward.
Some examples: I’ve been to the Maldives, Paris and Japan on rewards points.
What’s the best travel you ever scored?
Airline technology can sometimes mess up in your favor. When US Airways was getting acquired by American back in 2013 or so, I had redeemed 130,000 points for a first-class, round-trip flight to Australia. I was flying during the tech transition, and they ended up refunding all of my points. I flew to Australia for absolutely free.
Navigating points and miles requires a lot of legwork; travelers must compare the value of miles and dollars and points on different websites. Is it getting harder to nab good deals?
The technology makes it really interesting these days.
Before, you had to be an expert and know how to use 10 different airline websites. There are tools now, like seats.aero and Thrifty Traveler, that are a little wonky but not that hard to use. Award redemption is shifting, but with…
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