Seatmates: Brian Kelly
On turning instinct into a travel strategy, redefining what points & miles are really for, and why the tallest guy on the plane still chooses the window seat
This interview is part of Seatmates, a Window Seat series where tastemakers and creatives share how they move through the world—what they pack, where they stay, and the travel rituals that shape their lives.
There are travel experts, and then there is Brian Kelly. Long before points and miles went mainstream, he was teaching travelers how to unlock smarter, more empowered trips—lessons he later distilled into his book How To Win at Travel. But what makes him compelling now is how his philosophy has evolved: instead of points just unlocking upgrades, they’ve become tools for connection, protection, and creating the kind of memories that outlast any flight.
Since launching The Points Guy fifteen years ago, Brian has built one of the most trusted travel media brands and created a platform that has shaped how travelers understand and engage with the industry. The ripple effect is clear: millions travel better because he showed them—and me!—how.
Read on to learn his strategy for dodging delays, the rules he trusts more than any airline policy, and the counterintuitive seat choice he swears all tall travelers should make.
Tell us a little about yourself.
I’m Brian Kelly and I founded The Points Guy, a site that now helps millions of people travel better. What started as a fun blog back in 2010 has taken on a life of its own, and I never could have imagined what it would become.
But more importantly, I’m a dad to two young kids. I love to travel, not just for work but for pleasure, and traveling with my kids has been the adventure of a lifetime. My 11-month-old is even about to become the youngest person to visit all seven continents! I just took my three-year-old and almost-one-year-old to Antarctica for Thanksgiving, and it was absolutely incredible.
I split my time between my home in NYC and my farm in New Hope, Pennsylvania with goats, llamas, alpacas, pigs, chickens and more. I love animals, and having so many on the farm has been a blast for both me and my kids.
I started reading TPG because your advice always feels like playing a smarter game of life, not just travel. Given that, how do you define what luxury in the travel space looks like now? What was a moment during a trip that felt like the pinnacle of luxury to you?
For me, luxury is all about convenience—saving time, reducing friction, and removing stress. It’s getting VIP airport pickup or a Blacklane driver waiting at the baggage belt so I don’t have to worry about getting around in a foreign country, and can instead focus on enjoying the journey every step of the way.
To me, luxury also means having great people to help make the trip unforgettable. It makes a huge difference when you can get support from hotel concierges, credit card concierge teams, or trusted travel advisors who help plan smart, incredible itineraries. AI is helpful, but nothing replaces having a local expert who can recommend what’s actually worth doing—especially when traveling with little kids. That combination of efficiency and care is what feels truly luxurious to me.