Seth Kugel admits to not really knowing what the phrase “travel writer” means. But that doesn’t stop him from being one of the most beloved ones in the English-reading world. As the Frugal Traveler columnist for the New York Times, he writes about how to have—how he’s had—spectacular experiences all over the globe, even while holding tight to your wallet.

This isn’t exactly what he set out to do. If you were to map out his path to travel writing, it would look as rambling as his itineraries. First he wanted to be an archaeologist. Then he studied African governments at Yale. For three years, he taught third grade in the Bronx. Then he went to Harvard to get a public policy master’s degree. Then he worked for the city of New York, first in immigrant services, then in child protection. He started freelancing for the Times in 1998, and quit his day job in 2001. Once he became a full-time journalist, he used his fluent knowledge of Spanish and Portuguese to co-author a book called Nueva York: The Complete Guide to Latino Life in the Five Boroughs.

In 2010, he inherited the Frugal Traveler role from Matt Gross. Kugel’s first assignment: a 13-week bus trip from São Paulo to New York. Today, he travels much of the time, reporting his experiences, taking a bit of a curmudgeonly approach to writing, and maintaining a quippy—and very popular—presence on Twitter.

In this interview, he tells us that his dream destination might just be fictional, why he wouldn’t want to consort with Columbus (but that he’d be very interested in meeting a crew member of, say, the Niña or Pinta), and why buying a local newspaper whenever you arrive anywhere is good practice. We also found out which common question makes him cringe.

Describe your perfect day, from dawn 'til dusk. Where would you be, who would you meet, and what would you do?
Setting: A small city in a fictional country I’d never been to, with vibrant local culture, outgoing people who speak a language I am fluent in, and a reputation for strong espresso and skilled pastry chefs. I wake up in a budget-friendly, but clean and eccentrically decorated family-owned inn. Stumble downstairs, play with friendly dog, and high-five the owner’s children (whom I helped with their math homework the night before). Eat hearty breakfast that causes me to wonder for the 8,000th time how Americans got so hung up on cereal. Walk around the town, pop into a café for a double espresso, then stroll into shops and take pictures of historical buildings decently preserved but not to the extent they look like a museum or a campaign to make the city UNESCO’s eight-millionth World Heritage site.  Eventually wander into some place I’m not supposed to go, like an olive-oil factory or an artisan workshop or a wedding rehearsal, pretend I went in by accident, and finagle a free sampling or a tour or a last-second invite. Have lunch at outdoor market where the slight risk of food poisoning is mitigated by an irresistible aroma of a combination of spices I cannot place but remind me of something somewhere on another hemisphere. Choose a dinner spot famous for its five-dollar, 100-calorie, 13-course dessert tasting menu. Strike up a lively conversation with the people at the table next to me, and end up joining them for drinks at a small but raucous bar in a residential neighborhood I would have never thought to visit. Return to my inn, then go online to find that all wars have ended and that world prices for sugar and coffee are down, portending even cheaper espressos and desserts in travels to come.

If you could travel somewhere you've never been, where would you go?
Aside from the place I just described? I have a thing for huge countries, because even if one part’s not doing it for you, you can just take off for another region. Countries that fit this description best are Brazil, Turkey, Canada, Russia, and the U.S. Two that I haven’t been to but are at the top of my list are China and Indonesia. Both are almost certainly more interesting than Liechtenstein.

What’s the best place you've ever visited?
I despise this question. My best traveling experiences have much more to do with what happens, not where it happens. But let’s get it over with. Lençóis Maranhenses National Park in northeast Brazil. Desert-like dunes separated by crystal-clear fresh water lakes. Gorgeous, stunning, remote, etc. Just Google Image it.

If you could have lunch with any explorer, living or dead, who would it be and why?
I’m a Western Hemisphere kind of guy, so it would have to be a member of one of the European expeditions to the “New” World in the 16th century. Probably not the famous explorers themselves—their motivations were too politically or monetarily motivated for my taste, and some were bloodthirsty. Instead, some random crew member who really paid attention to the new landscapes, animals, and, of course, people he encountered. Far more interesting, though, would be to speak to the people that encountered them—though we can read endless accounts of exploration, there are few accounts of being explored.