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Meet Charles McCool, Travel Hacker Turned Travel Expert

Written by Dave Odegard

This blog post was updated on May 31, 2023.

The phrase “travel influencer” may seem like a fresh 21st century novelty — like the latest social media platform you’re still trying to figure out — but the concept of a professional traveler earning income by creating content around their adventures and experiences isn’t that new.

Just ask Charles McCool.

McCool’s been discovering the ins and outs of traveling the world for cheap then sharing and teaching what he’s learned for over 25 years. In fact, McCool (who’s been ranked by social media scorekeeper Klout as the #2 travel expert and written for the likes of Travelers United and Yahoo Travel), can do something that the plethora of today’s travel bloggers, vloggers, and Instagrammers probably can’t: Give a first-hand account of the Earth-shattering paradigm shift that forever changed the travel industry.

“Today, so many people are savvy and confident enough to book their own travel online but it was rare 25 years ago,” McCool explained. “Around 1992, the first internet consumers gained the opportunity to research and book their own flights.”

Although McCool admits that using early ’90s dialup to find and book cheap airfare was a “techy and costly process,” he cites it as the first major step to the online travel ecosystem that we know and love today. “[It] resulted in most travel agencies shutting down and travel suppliers shifting operating costs to consumers (self check-in, baggage fees, etc.),” he said, “along with empowering a couple generations of book-it-yourselfers.”

In the early ’90s, right when the then new frontier of online travel booking was being forged, McCool was working as a software tester. He ended up relocating for work to a part of the country describes as not being all that exciting or stimulating for a single guy in his 20s. “So I spent a lot of my free time visiting other places,” McCool recalled. “My analytical and curious nature led me to find alternative ways to travel more effectively…the kids call it travel hacking today.”

McCool would eventually refine his talent for finding flight deals, exploiting little-known airline policies, and seizing last-minute booking opportunities to travel to all 50 states and dozens of foreign countries. When asked to name some of his destination highlights over the years, he cheekily answered with “Alaska, Australia, Amalfi are so amazing…That’s just some of the A’s.”

But it was McCool’s combination use of the travel hacking skills he’d picked up to fly for two years to four different continents without paying anything that would confirm him as someone who knew how to play against the travel industry house and beat them at their own game. McCool compiled his techniques into a book, Winning the Airfare Game, which he published in 2001.

“My vision was to gain credibility as a how-to travel expert so that I could teach other people how to travel better,” McCool said. “Certainly there was a path to become a travel agent but there was no degree to be a travel expert. I sensed that writing and publishing a book would be my certification.”

Unfortunately, Winning the Airfare Game came out a month before 9/11 — which, like the advent of the internet, forever changed the travel industry and its rules…the very things McCool was advising readers on how to take advantage of. But putting his book together did lead McCool to formulate his underlying philosophy, which he now calls “Happy Travel.”

As a software tester, McCool learned that although he could be a pain to programmers, his role of hunting down potential bugs and glitches was key to preventing inferior products with from reaching customers, costing companies goodwill, money, and resources. “In essence, I was helping to create ‘Happy End Users,’” McCool explains.

It was a point of view that McCool brought to his new turn as a travel expert, giving advice on how to handle travel mishaps before they happen. According to McCool, it just takes some simple steps to prevent most of the problems that can ruin a trip. A good example? McCool suggests making sure that staying somewhere with laundry facilities every three to six days of your trip, which allows you need fewer clothes and pack less. “Packing light works for me,” he said. “It saves money, time, and stress. It makes me more mobile and allows me to enjoy the trip so much more.”

Another of McCool’s packing light tips: Buy your toiletries when you get there. It not only saves space in your bag, but can help create a more authentic experience. “Shopping for toothpaste, deodorant, or first aid items at a small pharmacy or shop in a rural European or Asian town is exciting, scary, enlightening, and memorable,” he explained.

As for the problems that can’t be prevented? McCool believes those can be a chance to improve one’s trip. “For instance,” he explained, “if I make a hotel reservation, confirm that reservation, show up and they do not have my room, then that is an opportunity — an opportunity to be upgraded to a suite, opportunity to get a room at a better property (and have them pay for it).”

It all leads back to what McCool outlines in his book as the “Principles of Better Travel.” Boiled down to their essence, they are: Be Flexible, Be Resourceful, Be Assertive.

“My most vivid travel memories result from serendipitous moments. Meaning, unmanned, spontaneous occurrences,” explained McCool, who advises travelers to try and leave one day of a trip unplanned and see what happens or even take entire trip with no reservations. “I once flew to Australia with no lodging or plans,” he said. “Super scary but also fun and memorable.”

And while the travel industry may someday quake and tremble with another unforeseen paradigm shift — be it to the latest booking app, airfare pricing model, or hospitality trend, McCool is confident the travel philosophy he figured out back then will still work. “Now 15 years later,” he said, “I still promote those principles to anyone who wants to be a Happier Traveler.”

About the author

Dave Odegard

Dave Odegard is an ex-army brat turned internet word person, whose work has been published on Maxim Online, USAToday, Buzzfeed, and more. He is currently the Senior Content Writer at Fareportal (CheapOair's parent company) and spends his free time exploring the wilds of Brooklyn, New Jersey, and Sweden.

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  • Fantastic post! Charles is a wealth of information and always willing to help anyone who has questions about traveling. You captured him well!