How to Win at Travel, by Brian Kelly (Avid Reader Press, 304 pages)
It’s hard to say whether Brian Kelly really founded the travel website known as The Points Guy, or whether his father actually did, because it’s Kelly’s father who set him on this path. When Kelly was 12, his dad let him arrange the family’s vacation using points he’d accumulated from airlines and hotels, and a traveler influencer was born. Before he even had a driver’s license Kelly was hooked on the game: how to travel the world, in style and at minimal cost.
As an adult, he went on to start a website in order to share his strategies, and “The Points Guy” took off after he was featured in a New York Times article in 2011. Now Kelly is a dad himself, he’s sold the website, and he has compiled a couple of decades of travel wisdom into a book that arrives just in time to help navigate your summer vacation.
Kelly calls this the “platinum age of travel,” arguing that it’s never been cheaper and easier to go so many different places if you know what you’re doing. Problem is, he says, most people don’t — unless they travel a lot for business, or grew up in a family that had the resources to travel, most people have never learned to travel well — it’s not something that’s taught.
“You may think travel is horrible across the board, but it’s amazing when the system works for you. When I travel, I rarely wait in lines. I don’t pay for food and drinks in airports. You can do the same, and I’ll show you how,” he promises.
Kelly begins by inviting readers to decide on “travel goals” and to set a travel budget, which right away may lose him some readers whose travel budget allows a day trip to Worcester, Mass. There is a smattering of generic advice in this section, some of which seems obvious (“Stay at hotels if safety is a concern or if you’re traveling alone”), but some of which is surprising (he advises travelers to wear backpacks on your front in crowded areas lest a thief slice the bottom of your bag without you knowing it). There’s high season and low season for travel, but there’s also “shoulder” season, the bridge between the two that is often the best time to go. And so forth.
From there, Kelly organizes the book into how to win at different aspects of travel: booking, earning and redeeming rewards, accessing perks, navigating lines, traveling with family, staying healthy, dealing with problems that arise, and managing fear of flying.
Again, some of the information he shares is intuitive: Your odds of having a flight delayed or canceled are the lowest earliest in the morning, for example. The more prestigious airlines (read: Delta) are usually more reliable. Where he gets into the granular stuff is where it gets interesting, as in one of his tips for booking cheaper flights. If you are, for example, in Oklahoma City and want to go to Tokyo, he advises that you buy a ticket from Oklahoma City to Los Angeles, and then book a separate flight from Los Angeles to Tokyo, thus (by his calculations) making the trip half of what it would have cost booking from Oklahoma City to Tokyo. This is a practice that travel junkies call repositioning flights.
The points and miles redemption chapters are where Kelly gets deep into the weeds, and readers will need to already have some knowledge of this game, or a burning desire to learn, or a couple of over-the-counter headache relief pills to keep up. He describes the machinations involved in getting the best values by accumulating points and moving them around and looking for “sweet spots” and planning “open-jaw” itineraries. (To be fair, Kelly does acknowledge, “If you’re a beginner, this chapter may get confusing.”)
Nor did I particularly enjoy reading about all the luxuries that all you people with access to airport lounges are enjoying while I’m waiting outside my gate. (You have showers? And buffets and VIP customer service?) I’m getting a bit grumpy at this point, I will acknowledge, since Kelly had promised me that I, too, could enjoy all the perks he’s enjoying, but he didn’t mention that I might need a Platinum Amex and elite status on Delta (which requires spending $28K a year).
As for easing the pain of lines, his advice is not novel (TSA PreCheck, CLEAR and Global Entry), and there have been reports lately of PreCheck lines being longer than regular since so many people have it, so that’s not even guaranteed to help.
Things get interesting again in the “flying with families” section because, despite having flown with four kids over two decades, I did not know that there is a debate over whether children should fly in first class (Kelly has done so) and that some people fly with “sorry gifts” to offer people who are upset by their crying or misbehaving children — like George and Amal Clooney, who once gave noise-canceling headphones to others seated near them on a flight. (Kelly’s against it — “Babies have a right to fly just like anyone else, and these types of gifts set an unnecessary precedent that we need gift packages to tolerate small humans.”)
Finally, Kelly offers some valuable nuggets on dealing with the inevitable problems, such as politely asking to be upgraded to first class on a flight to make up for the inconvenience if you are bumped from a flight or miss a connection because your flight was delayed. He also suggests contacting the airline via a DM on X if your flight is running late, asking them to “protect” you (hold a seat) on another flight in case you miss your connection. “Not all airlines will do this, but it never hurts to ask. Plus, asking to be protected makes you sound like a pro traveler and someone they want to keep happy as a customer.”
Kelly is a likeable guy who is enthusiastic about what he does, and he can make you think a little harder about how to improve the travel experience for you and your family. It’s unlikely that this book will overhaul the travel experience as promised for the casual traveler, and it feels a bit long for the amount of useful information gleaned. But at least those of us still without lounge access can save money by dispensing with the “sorry” gifts. B-
Featured Image: How to Win at Travel, by Brian Kelly