A Conversation with Lee Abbamonte — TripIt Blog

BySteven I. Green

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Going Places is a new series from TripIt that highlights frequent travelers to showcase their unique travel styles and insider tips. 

For world-record holder Lee Abbamonte, picking where to travel to next is not only about the destination, it’s also about deciding how to get there, who to invite, the time of year, and weighing variables like: should he spend points and miles, or cash? Does he want to rent a car, or rely on ride shares? 

All of these factors matter when you’ve already visited every country in the world—and you’re the youngest American to ever do so. 

Of course, there are myriad other variables to consider when traveling during a pandemic. “Before COVID-19, I would travel internationally to 30 or more countries per year,” shared Lee. “Due to the uncertainty around travel restrictions, I took just three international trips in the past two years. But, in the meantime, I’ve traveled a lot more domestically—and thought about what’s next on my bucket list.” 

So, what are those bucket-list destinations at the top of his list? “Tripoli, Libya; and Socotra, an island off the coast of Yemen.” 

Lee is no stranger to getting off the beaten path when he travels—even if reaching his destination requires multiple attempts. 

“My favorite place I’ve ever visited is the South Pole. It’s so unique, so difficult to get to, and so few people have done it,” he said. “My first expedition in 2013 failed; the conditions just weren’t right for us to complete the trip.”

But Lee had his eye on the prize, and the next year, he was able to complete his expedition. 

Stats on stats on stats

While not every trip can be as memorable as visiting the South Pole, when you’ve visited every country, U.S. state, national park, baseball stadium—and the North Pole, for that matter—you still want to keep track of everywhere you’ve been. 

So, how does Lee stay on top of his past and future travels? “TripIt, of course! I’m a stats nerd, so naturally, I am obsessed with TripIt’s Travel Stats feature,” he said. 

Lee also uses TripIt to keep all of his travel bookings and confirmation numbers in one place. 

“I use TripIt—religiously—to build itineraries for all my trips. From tee times to restaurant reservations to tours, I rely on the app to keep me organized. Plus, it’s just so fun to look at; to see what I’ve planned, and where I’ve been.” 

Expert tips for dream trips 

Using TripIt to stay organized aside, Lee shared some other tips for fellow travelers. 

First up, where to go: “Africa, in general, but the country of Namibia, specifically. It’s a beautiful country with wide-open spaces, gorgeous beaches, and sophisticated cities. It’s an under-the-radar destination I can’t recommend enough,” he said. 

As for tips on how to get there (or anywhere)? “It comes back to weighing those different variables. Think about what makes more sense for your travel budget—do you want to book with cash, or do you have points and miles to use to help you offset costs? Do you want to spend money to rent a car for a week, or can you get around on public transit or ride shares?” 

Lee also recommended comparison shopping, i.e., not booking the first flight or hotel option you find. “Shopping around for your flights and accommodations can save you hundreds of dollars,” he said. “And when you do decide on a flight, use TripIt Pro’s Fare Tracker feature to find out if the price of your airfare drops after you’ve booked.” 

Lee’s also a big fan of leveraging the sharing economy when he travels. 

“The sharing economy has changed the way we travel,” he said. “Whether it’s vacation rentals, like Airbnb, or ride-share programs—these options give you more flexibility to save money, making travel more affordable and accessible.”

His final tip? “When it comes to travel, there’s nothing to it but to do it,” he quipped. 

Indeed, Lee is an inspiration to all of us travelers to go after our travel dreams, be persistent when a plan doesn’t work out the first time, and to reflect on where we’ve been—whether it’s with the help of travel stats, snaps, or something else. 

Want to keep up with Lee’s future travels? Follow him on Instagram and Twitter to see where he’s off to next (hint: palm trees are definitely on the horizon!).

About the Author

Amanda Wowk

Amanda Wowk is a freelance writer, founder of Amanda Wowk Creative — a content writing services company — and avid traveler. Her experience spans the travel industry, supporting clientele in travel tech, luxury travel, and consumer brands. When she’s not helping clients tell their stories, Amanda writes about her own experiences to inspire others to travel as far, wide and frequently as possible.




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