Reviewed by Nancy Wigston
Once upon a time, Brian Kelly’s father handed his tech-obsessed son control over the many points he’d accumulated while traveling to California working for a healthcare startup. He thought his family of six might use the rewarded air miles and hotel loyalty to vacation in Florida. Then drive home to Philadelphia. Instead, in 1996, all six—traveling in two batches—enjoyed eight nights at a vacation rental in The Cayman Islands, under Caribbean skies. When Brian and his mother arrived to join the others in Grand Cayman via Miami, his father was waiting at the airport, beaming with joy. And why not? Brian had created a magical family break. He was twelve years old.
Years passed, and Kelly left the financial sector in 2011 to become The Points Guy, a blogging travel maven admired by the New York Times and famous in the internet world. After quitting his “stable job at Morgan Stanley” after the crash of 2008, he later treated his mother to a cheap business class trip to Easter Island, where his blog fans recognized him— “You’re the Points Guy!”—allowing him to bask in her parental admiration. What had begun as a fun side hustle, had bloomed into a popular blog and by 2011 a full-time career (he’s since sold the company).
How to Win at Travel aims to share what Kelly, writing this memoir as himself, has learned about travel’s “lucrative ecosystem.” He patiently explains that his initial fascination with hidden airline costs began after watching a 60 Minutes segment showing passengers had paid widely different prices for the same seats. How not to be “the fool” who paid three times what his seatmate had paid? Kelly rose to the challenge.
“The deals are there, but buyer beware.” You must be flexible, do your research, take time to find deals and weigh costs logically, he advises. A dedicated list maker, Kelly typically numbers the factors to consider before booking: Is this a good fare based on historical rates for this route? For this data he consults Google Flights or Hopper for data about low or high fares. Can I earn frequent flyer miles or elite status? What fees or exclusions come with this fare? Do I get lounge access, or can I cancel? Is the airline reputable? Can I book this directly with the airline so I can deal with them in case my flight is delayed or canceled?
First of all, forget your nostalgia for the Golden Age of Travel: it didn’t exist. Travel was dangerous and expensive. In 1970 there were numerous fatal plane crashes and seventy-eight hijackings. Despite the spate of recent crashes (on which networks focus because they are cheap to cover,) ours is the Platinum Age of Travel and points and rewards are the way to win the game. In the 320 pages of this book, Kelly shares his experience and the tips he’s learned over decades playing the mental sport that is modern travel.
Compare the old days of multiple stops, onboard smoking, and endless hours spent in loud cabins before reaching your destination, to today’s non-stop flight between JFK and Singapore, lie-flat beds, multiple choices of movies and TV shows—and music—not to mention greater efficiency and safety. Plus, you can maximize your airline and hotel reward points to impressively reduce costs—in every area of your life.
Pay attention, students! This man has been to 80 countries and possesses 28 credit cards (22 of them transferable).
This may be an American thing since most of his fellow citizens have at least three credit cards, which is not the case worldwide. Never accumulate credit card debt, he counsels and know your credit score. Moreover, he really likes to travel and uses words like “spend” as a noun and introduces terms like “fat finger” to explain how a ridiculously low fare can suddenly appear by mistake on an airline’s website. Don’t hesitate to grab it.
There’s a wealth of detail here—get insurance, be meticulous with your documents, and be alert. “Cheap Can be Expensive” is a warning you’ll hear often. Oh, and don’t hoard your points or hang on to Elite status if you no longer need it. It’s like a drug.
Change, Kelly reiterates, is the one constant in a travel world that is ever—expanding (especially after lockdowns). Alert flexibility, he admonishes, is key to mastering the system, flying first class, avoiding long airport lines and enjoying perks like lounge access with free food, drink, and helpful, knowledgeable staff–plus free nights at hotels courtesy of loyalty memberships. Once these travel benefits were restricted to the wealthy. Today, they are within reach of any frequent traveler clever enough to play and win–the game. Remember that twelve-year-old in The Caymans? He’s now flying business class to scuba dive in the Maldives.
After the pep talk—thanks coach! –come Brian Kelly’s lessons about navigating the petrie dishes of society” at airports and winning the sport of travel by knowing its sometimes tricky smorgasbord of rules. Kelly was in college on 9/11, and fled his high-rise dorm in Pittsburgh, fearing attack. Afterward, with major airlines in financial trouble, he noticed a proliferation of low-cost carriers like Southwest offering air miles on $40 domestic short-haul flights whereas similar routes on American Airlines had cost $300 during travel’s previous “Golden Age.” That’s how he flew on points to Dublin as a cash-strapped student, a pattern he learned to exploit and share with friends.
The value of points as currency became clearer—once he paid $20,000 to fly himself and a group of friends to the Greek island of Mykonos. They paid him back and Kelly, in return for his initial cash outlay, acquired all those airline points, a bonus for making the group arrangements. No doubt his child will grow up, like his dad, using Goole Flights to discover the best deals available. After that first step, he “always goes” to Amex Travel and if some site sounds dubious, he checks them out on Trust Pilot, Reddit, or Flyer Talk—review sites for deals.
Kelly knows of numerous helpful sites like Flyer Talk, all familiar to him from his early days as the Points Guy blogger–there seem to be dozens and some demand fees. Sometimes it seems we’ve entered the complexities of the Medici court, centuries later. Kelly’s discussions of high-status cards, often called “platinum” or “gold,” the ones granting air miles each time you use them—may seem somewhat baffling to the tech-deficient brains among us—and his intense tutorials about which bank’s credit cards offer the best travel deals may incline some readers to drop out of class, exhausted.
But not Brian Kelly, boy internet genius. He consoles us by saying his book is only a treasure map, a guide, and that we’ll need to continue, do our own research after reading. Plus, he’s relentlessly cheerful, generous about sharing his decades of knowledge, charitable with his points, and optimistic about the future of air travel. And several of his tips are newsy and easy to digest. Who knew that many cities are far cheaper departure points than larger ones–try Colombo, Cairo, and Karachi for cheaper fares–none, alas, are in North America but very handy if you live in Dubai.
And the stories he tells about the adventures and misadventures of today’s travelers are entertaining —like the charges brought against a tourist in Thailand who shamed his hosts by giving their accommodation a one-star review, or the imprisonment in the UAE of a British man for having too many of his own prescribed anti-anxiety pills.
Once we exit the weeds of mathematics, points accumulation and transfers-a sport at which Kelly enthusiastically excels- he’s free to guide us through the modern airport–the aggravation of flight delays, rebooking—always be kind to airport staff if you want the best results—what to do about crying babies (get over it, help if you can). Traveling with little ones is one challenge, with big ones is another —don’t drink alcohol and have all the necessary meds with you. He doesn’t say it—he doesn’t have to– but wrangling first-class status (lounges! pajamas! showers! kind attendants!) makes the whole experience more pleasant.
Jet lag? Yes, he gets it and offers insights about who is prone to it and ways to manage light to ease its effects. Flying from Tokyo to NYC throws even Kelly’s circadian rhythms off track, so he offers various tips like taking melatonin (adding “I’m not a doctor”) to wearing sunglasses on the plane to fool your brain into thinking it’s nighttime and knowing whether you’re a “night owl” or “early bird” by nature. Alas, there seems to be no easy cure, and he corrects Taylor Swift’s claim that it’s just a mental condition.
High status or low, there’s no denying that the modern airport can be stressful. So don’t kick off your flip-flops or show other gross behaviors, and above all, don’t forget your empathy. There’s a real shortage in the traveling world that urgently needs to be addressed.
Often asked about his favorite flying experience, Kelly doesn’t hesitate. He shares a heartfelt memory of a cherished Points Guy flight. Partnering with American Airlines and the “Make a Wish” Foundation, he joined children’s entertainers—he was the M.C.–aboard a planeload of children heading from JFK to Orlando. All the passengers in the airport applauded, as the children, each granted V.I.P status, boarded the plane. It’s an inspiring scene, showing the Points Guy at his most fulfilled, paying it forward.
Nancy Wigston is a Toronto-based travel writer. Please see her recent book reviews of Gobsmacked – The British Invasion of American English, A Travel Guide to the Middle Ages, and Dickensland: The Curious History of Dickens’s London.