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.
Points, miles, and status are all quantifiable, but emotions while traveling are not. Has there been a trip that changed how you feel about the world, yourself, or TPG’s mission? How do you incorporate emotional “ah-ha” moments into a business built on metrics?
Absolutely. Travel is so much more than flying first class or checking out the newest hotels. It’s definitely a lot of fun to travel for the most luxurious experiences, but the most meaningful trips in my life have been through PeaceJam, an organization The Points Guy has partnered with for more than a decade.
We bring Nobel Peace Prize Laureates to youth in countries like Guatemala, Ghana, Liberia, and South Africa. We also bring TPG team members on these trips, fly in the Laureate, host youth peace-empowerment conferences, and help build communities of young leaders who all want to create a more peaceful future.
Those moments—watching young people feel seen, inspired, and supported—remind me that points and miles aren’t just about upgrades. They’re tools that can help connect the world in a real, human way.
You use a lot of data and logistics when traveling, but the best trips can still require intuition and a bit of serendipity. Can you remember a moment you ignored all the “smart travel rules” and went with your instincts—and what came of it?
There have been lots of moments when I went with my instincts, especially when traveling. When I get a gut feeling that my flight may get delayed or cancelled, I immediately jump into action: I book backup flights using miles, I monitor alternatives, and I don’t wait for the airline to rebook me.
This is advice I give everyone: don’t wait for the airline. In the U.S., there’s no real passenger bill of rights, so you have to be your own advocate. People often don’t realize their credit card offers amazing protections—trip delay insurance, lost baggage coverage, and more. Sometimes instinct and preparation beats any official policy. That’s the real value of points and perks: they give you options in moments of chaos.
What’s been your most memorable stay?
This is tough! I’ve stayed in many incredible places, but the one that stands out is Cheetah Plains in South Africa. I took my parents and my then-two-year-old, and we had the most extraordinary safari experience.
Watching my toddler fall in love with the wildlife—and sharing that moment with my parents—was an intergenerational travel memory I’ll never forget. It blended one of my lifelong passions with one of my favorite countries in the world, and being able to experience that with my loved ones was priceless.
Is there a destination or property at the top of your wishlist?
High on my list is a scuba-diving trip to Raja Ampat. There are these stunning Indonesian liveaboard vessels (like Rascal Voyages) that take you to incredibly remote areas, from Komodo to Raja Ampat. A true expedition out there is a dream experience I’m hoping to make reality soon.
What are your must-haves when it comes to luggage and items you travel with?
You absolutely must track your luggage. I’ve recommended AirTags for years, but lately I’ve been loving July’s new CaseSafe luggage because it has tracking built right in—and it’s surprisingly affordable.
I’m also a Burt’s Bees fan. I always pack Chapstick and moisturizer because travel can wreak havoc on your skin. Simple, reliable essentials make all the difference.
What is your go-to airport outfit?
Comfortable but polished. I usually wear Lululemon ABC pants—they look put-together but are incredibly stretchy. I pair them with a T-shirt and a nice jacket like my Issey Miyake pleated blazer to elevate the look without sacrificing comfort.
I’m a Nike sneakers guy, and because I run hot (especially on airplanes without air vents), I often bring Lululemon lined shorts to change into for sleeping. Pro tip: if you’re roasting on a plane, ask the flight attendant if they can lower the temperature in your section. Most are happy to help.
Do you have any rules or rituals when it comes to air travel?
For me, everything starts before I leave the house. I use the Flighty app to track where my plane is coming from and whether it’s delayed. I’ll check FlightAware to understand weather issues, and I always look at what’s happening across the airline’s network.
If I sense irregular operations, I start planning backup flights or consider using miles on another airline if I absolutely must get somewhere.
I try not to show up too early unless there’s a lounge I really want to visit, like the Chase Sapphire Lounges or Delta One Lounge. Otherwise, I’d rather spend extra time at home with my kids.
Last question: aisle or window seat?
Window seat, always. People are shocked because I’m tall, but for tall travelers the aisle can be a disaster. You get hit in the face by backpacks and your knees become target practice for the drink cart.
In the window, I get space, the view, and control of the shade (which rightfully belongs to the window-seat passenger! Ed note: can we finally end this debate now?!). In exit rows or first class, I have plenty of room and can actually enjoy the flight.
For more, follow Brian on Instagram. Interested in being featured in Seatmates or know someone who should be? Drop me a line here.
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Tori Simokov is a Travel Writer and Graphic Designer/Strategist based in New York. To get in touch, email tori@v1projects.com. Want more? Check out Instagram, TikTok, or shop her curated favorites.
Love Brian and his work. The true king of travel! I’ve learned so much from him.