Travel can be complicated. Where does one start when there are countless websites, podcasts, and social media resources for tips and deal alerts? It can be very overwhelming! Enter Brian Kelley’s book, How to Win at Travel. Kelley, who started The Points Guy in 2010, is mostly known for points and miles travel. The book covers plenty of points and miles matters, but he also dives into dozens of other topics including insurance, safety, traveling with kids, loyalty programs, search tools, and more. If you are interested in learning the basics of points and miles travel, or want to make traveling easier, this book may be of interest to you.
“While the internet and social media are helpful resources, we’ve gotten to a point where there is just too much information, and rampant misinformation, making it difficult to figure out how to win at travel. If you are hoping to build a solid foundation for travel, and learn how to travel better, more affordably and savvier, this book is for you.” –Brian Kelley
Kelley shares bits and pieces of his travel origin story, beginning at the age of twelve when he planned a family vacation with points his father earned through business travel. Lavish vacations were not the norm for the Kelley family, but Brian wanted to dream big, and he loved a challenge. Using his internet savvy, he successfully booked a vacation to the Cayman Islands for the family of six. His family was thrilled, and he was officially hooked on the points and miles game.
By the time Kelley entered the workforce, he was booking travel for friends and coworkers, and earning massive numbers of points and miles. Eventually he started sharing his knowledge through The Points Guy travel blog, which blossomed into a thriving business. Although Kelley has since sold The Points Guy, he remains as a spokesperson. Today, the website primarily pushes their credit card affiliate links, and shares basic travel news and deals.
In How to Win at Travel Kelley breaks down the basics of points in miles travel, and shares many tips for earning and redeeming points. But if points and miles aren’t your thing, there are plenty of other tips. As a new father, Kelley has lots of advice about flying with infants and toddlers. He discusses boarding strategies, packing, strollers, car seats, and other safety issues. Other chapters cover tactics to avoid lines, the in the ins and outs of stopovers and layovers, and how to expedite passports. I found the chapters on how to manage travel stressors, and what to when things go wrong particularly interesting. Kelley covers jet lag, fear of flying, lost luggage, cancelled flights, and more. Clearly, Kelley covers a lot of information in this book, so not all topics may apply or be of interest to every traveler. Although you can listen to it as an audiobook, you might find it easier to navigate in printed form, so you can easily find the topics of interest to your travel style, and skip over the rest. Like The Points Guy website, Kelley places a lot of value on luxury travel and securing amazing points redemptions. This style of travel and the effort it takes to obtain a large stash of points won’t appeal to everyone, but most readers will likely find some good tips to make reaching their destination a little easier and less stressful.
Kelley, Brian. How to Win at Travel. Simon & Schuster, 2025.
