By Sarah White

So many people wish they could make a business out of doing a thing they really love. My friend Cathy Fleming does just that. This interview is the first of a two-part series in which I reflect with Cathy on how she found the best work of her life. In Part 2, I write about my experience traveling in Italy with Cathy in Fall 2021.

I was 23 years old and not sure what I was doing in college, studying art, especially Italian art history. A friend told me about an opportunity to work for a family in Assisi, Italy as an au pair. I just decided, “Okay, I’ll go do it for a year.” Soon I was there, teaching English to their children in the afternoons and studying at the University for Foreigners in Perugia in the mornings, going back and forth on the train. After nine months or a year, I left the family and did some independent traveling. I basically hung out in Italy and worked, between 1983 and 1986, with some breaks to come home and visit my family.

I know what happened next because this is where I came into the story. In 1986, I owned a small graphic design firm. I hired Cathy, newly returned from Italy. She worked for me for several years, then left for a work opportunity in Africa. She returned to the U.S. in 1991, settled in the Milwaukee area, and worked in marketing. Before long, she married and moved back to Madison.

After little Max came along, the years just flew by. When I was approaching my 40th birthday, Tim said to me, “why don’t you go do something special? Why don’t you go to Italy? Call those women you always talk about, that you had so much fun with. You go, I’ll stay back and take care of Max.”

That was before the Internet, so it required detective work to find her old friends, but she did. In July 2000, the three friends headed back to Italy for nearly a month.

We ate and drank our way through Italy and discovered all kinds of new things. And it turned out to be a few weeks of self-discovery, too, because I realized how interested I was in the producers of all that great wine and food, connecting with the local life.

Here’s where Cathy’s branching point came—the moment when everything changed.

After I came back, just talking about my trip with friends, people were saying, “I would love to do that. Maybe you should put a trip together so we can all go.” In the back of my mind, I knew I wanted to reconnect with travel and life abroad. I decided I should just do a trip. Then I started thinking about it as a business. I began doing research. Back then, a lot of it was still reading travel magazines, food and wine magazines—not everybody was online yet. I was reading and making notes and contacting people. Then I set up meetings and in 2002, I went on a research trip. I met with wine producers, olive oil producers, hotels. I came back and started putting all the pieces together. I started Viaggi di Gusto—which means “Travels with Taste”—and took my first tour group to Italy in 2004.

And I’ve been following you ever since. One thing that has amazed me is the number of repeat customers you get.

That has driven me to discover new places because they’ll share interests with me or places they want to go. I’ve had one couple travel with me nine times. There are others who have gone with me six, seven, eight times. They become friends. That’s been really gratifying.

Being a travel specialist means taking on a lot of responsibility. What is the most unusual experience you’ve had? Something surprising, challenging?

I’ve had maybe two or three occasions where someone needed to go the hospital. Those experiences with doctors were actually just great; they’ll see you anytime, like six o’clock in the evening, “come to my office.” I think the most unfortunate thing was a time I hired a driver for my group in Tuscany. He kept missing so many turns, getting lost, it was very weird. I finally figured out he was functionally illiterate. That was not a good situation.

I think it speaks to your grace under pressure that you got your group through that. That’s something I admire about you. Speaking of challenging experiences, how did your company fare during COVID?

That was a very confusing time for me. No one knew what to expect. I had to stay positive even as I canceled trips. I was worried about the people I’d worked with in Italy—a lot of them, the guides and chefs, lost their income. I offered some virtual cooking classes and virtual guided tours, but in those cases, I didn’t take any money. I sent it all over to the chefs and guides. But at least, for me, that was a way to keep prospective travelers engaged and interested in my services when I couldn’t actually offer trips.

I traveled with you on one of your first trips in Fall of 2021, when you could finally get back to business.

It was thrilling to be back. Remember how empty the Colosseum was? Now, the demand for travel in Italy is up, up, up. I’m scheduling 2023 tours and they’re filling fast.

It’s always been a dream of mine to take a group of writers to Italy. If I do, it will be Cathy I’ll ask to plan the trip. Travel isn’t the time/place for deep writing–there’s too much to do! But we can make use of the stimulation of new scenery and cultures to deepen our powers of observation and sense-making. Who’s coming with me? You, maybe?

To contact Cathy, follow this link.

To read Part 2, follow this link.

© 2023 Sarah White