Compromises, bribes and a 400-year-old finger: The messy reality of getting my teenager to love Italy

One sparkling summer evening last year, I met up in Florence, Italy, with an Italian friend I hadn’t seen in years. After strolling through Piazza della Repubblica, Chiara and I lingered over novels at a bookstore and then had a long dinner at a lively restaurant near the central market. It was a thrill to catch up with a friend in the enchanting Tuscan city where we’d first met. My 13-year-old son, however, was with me, and after we said goodbye to my friend, he cut short my reverie. “That was three hours of hearing you talk, talk, talk Italian!” Leo yelled. He was tired, bored and angry. It was the same tone he’d used at the Uffizi, a world-class museum crammed full of Renaissance art. My husband and I had avoided taking him there before he was old enough to appreciate it, or so we thought. Our visit wound up being a mad dash past Botticelli paintings as Leo aimed to leave as swiftly as possible. On the way out, I craned my neck at all the art I wasn’t seeing. What’s more, when he’d learned that we were going to some cities from previous visits, he moaned, “What? Again? We’ve already been to Rome and Florence!” Ah, to be a jaded 13-year-old who’s not always aware of his privilege. What did impress him in Italy? Pokémon cards, a pricey Ferrari shirt and a touristy museum of illusions. He also enjoyed playing the card game Uno No Mercy, which we could have done at home. Oh, and the expensive café on the roof of the Uffizi? Yeah, that was good, too. It was Leo’s third trip to Italy and one of nearly 10 international trips already under his belt. We were visiting a country where I’d experienced a pivotal semester abroad, which led to a stint as an expat after studying Italian in college. None of that mattered. Either he was hot or bored or needed to use the bathroom. Or I’d overscheduled our day — something I loathe doing stateside. Traveling with children overseas is often challenging. My fierce attachment to Italy made it even harder. Why didn’t he love everything about the place that changed his mother’s life? But since I’m on a mission to convince Leo to fall for Italy, I’ve learned — mostly the hard way — to compromise. And despite some disagreements, my efforts have started to pay off. In fact, he makes the trips special — a thoroughly American boy who nonetheless shares a first name with Leonardo da Vinci and dreams of owning a Ferrari one day. Here’s what I’ve learned while traveling to Italy with my son. A funny thing happened on the way to the forum The afternoon we landed in Rome during our first family trip to Italy in 2018, I found myself renting a somewhat rickety quadricycle in the famed Villa Borghese park north of the city center, even though I was exhausted. Leo, who was five at the time, had spent our 10-hour flight squirming while draped across my lap. The heat that July day was stifling, and even though the park was near our hotel, it was hard to enjoy it because every minute there felt like standing by an open oven. The Villa Borghese is full of ancient marble statues, which Leo largely ignored. Already a keen admirer of Italian cars, he was much more interested in how fast we could round corners in the park while in the quadricycle, even if it meant nearly tipping over. He cackled with joy while steering this four-seat open-air vehicle that Italians call a rickshaw. The Roman Forum — and my nap — would have to wait, as would the excellent art museum that’s inside the park. The compromises continued during a return visit to Rome in 2022, when I found myself ransacking the city for Pokémon cards after an evening of al fresco dining started to wear on the patience of my fidgeting 10-year-old. One moment I was out with friends, the next dashing over to a bookshop. Italian novels are my passion, and I’d visited Mondadori, one of Italy’s largest booksellers, many times. But until that trip, I didn’t realize they stocked Pokémon cards. If I sound accommodating, while standing in line I fumed to myself, “This wasn’t what I wanted to show Leo in Italy.” When we finally went to the Roman Forum, I certainly hadn’t planned to cut short the visit because Leo needed to go to the bathroom and preferred to return to our lodgings. I managed to prolong our visit long enough to stick my head inside of the Temple of Venus but quickly had to throw in the towel. It was hot, he was tired and nothing could salvage the outing. But the scene was quite different at the museum in Florence that houses Galileo’s finger. The Italian astronomer died in 1642 so the finger is exactly as decrepit as you’d imagine, even through the museum’s protective glass case. But Leo, then aged 10, loved it. He was thrilled to learn admirers had severed the persecuted scientist’s middle finger when his remains were moved in the 1700s. If the finger felt like a gimmick, so did the overpriced drinks — in every city and at every stop. But that kept him entertained, as did his gaming console, which came in handy last year in Rome, when my husband and I slipped out to Piazza del Popolo for a glass of wine. I had qualms about leaving my son alone in an apartment in a foreign country — but Leo didn’t. The best Italian insults I also had qualms about what felt like millions of euros spent on tickets, half-eaten meals and a pair of sneakers that we hastily bought at the outlets near Florence because Leo had only packed Crocs. So I was eager for a cheap but meaningful outing, and I arranged a lunch with another Florentine friend. Cristiano has a one-liner for every occasion; during a previous trip back to Italy, he’d told me not to worry that I was losing my Italian skills by returning to live in America since I wasn’t making any new mistakes — just the same ones as before. Ba-dum-bum! He often likes to joke that his English isn’t very good because he had a bad teacher (me). When he asked if Leo knew Italian during our 2022 trip, I admitted only a little. “Leave it to me,” he said. At lunch in a piazza not far from the city’s Arno River, we ordered an antipasto and some primi before catching up. Then after asking for a piece of paper, Cristiano said, “How about that Italian lesson?” I handed him my travel diary so he could write his “lesson” directly into the notebook. As the two of them began chatting, I took a photo and beamed at my husband. A native speaker — and a dear friend — was giving our son a personalized Italian lesson! But I snapped to attention a moment later when I realized “cornuto” was the first word of the lesson. Strictly speaking, it isn’t a curse word — it simply means a cuckolded husband. Yet in a land where machismo still reigns, it’s considered a rather severe insult. When I looked at my notebook later, I saw Cristiano had drawn the accompanying hand symbol for cuckold — the pinkie and forefinger sticking out over the folded middle fingers — a universal symbol for bad luck in Italy. I’ve marveled endlessly over Italian but nothing really beats learning — at age 13 — the word to describe a man with a philandering wife. An Italian holiday for all Part of the challenge while traveling with children mirrors the general trickiness of parenting: what entertained a child when he was five may not work when he’s older. During our first trip to Italy as a family, Leo gushed over every monument. Our photos — of Leo smiling at the Vatican and posing at scenic overlooks — attest to that. At age five, he was simply happy to be with his parents while experiencing new sensations. But the boy we took to Italy the summer he turned 13 was no longer easily amused. The evening in Florence when we had dinner with my old friend, Chiara, I’d made sure some of the conversation was in English and there was food at the restaurant that he liked. But it didn’t matter. He’d learned that when I visit Italy, I’m totally seduced by Italian culture. His outburst following the dinner touched on the central tension. In Italy, I want to linger at the counter of every café I visit, and eavesdrop on a barista bantering in Italian with customers. I’m lost in a reunion with a world first encountered during the golden period of my life when I was a 20-something expat — the years against which all others are judged. Indeed, after three completed trips as a mom, I’ve now concluded the biggest compromise when I travel to Italy with Leo is accepting a holiday that’s much less about Italian cultural immersion, so that it’s one he can enjoy, too. That means passing up moments that are far more magical to me than to Leo. Last year, as we crossed Piazza della Signoria in Florence one evening, there was an opera singer holding a concert in a loggia. Could we linger to hear her sing, I asked him? No. He was ready to call it a day, and the unearthly beauty of the aria in such a gorgeous setting was lost on him. The next morning, I reminded myself that Leo is still a kid. This was clear when we embarked on a hike with my close friend, Giovanni. During the long car ride to his house, Leo complained, and by the time I greeted Giovanni and his wife, Veronica, in Italian, he seemed somewhat sullen, tuning us out. I began to worry; would this be one more frustrating afternoon? But then it emerged that Giovanni was bringing a dog named Dante along with us. Leo reached for Dante’s leash immediately and took charge of walking him during our long hike in the mountains outside of the Tuscan city of Pistoia. As we hiked, I could hear Leo beckoning to the dog, “Here, Dante, here boy. Who’s a good boy?” In the end, he was a 13-year-old American boy far from home — and his own dog — who needed a simple pleasure that had nothing to do with Renaissance art. He just wanted a dog to play with — and woof-woof was a language he understood. Moments of pure delight The trips, of course, have offered far more than compromises. On our way to a rented house in Puglia, in Southern Italy, during our 2018 trip, we stopped for gas around lunchtime. The service station, which was in a small town on the Adriatic Coast, also housed a restaurant. Good food is everywhere in Italy — even at highway rest stops — so after filling the gas tank, we sat down to eat at a table outside and I ordered spaghetti alle vongole — pasta with clams, an Italian seaside specialty. From our table, I could see the gas pumps, and also a selection of cheap beach toys for sale in the service station market. I’d never eaten at a gas station. But it didn’t take long before I declared it the best spaghetti dish I’ve ever had. Leo laughed out loud. “You had good spaghetti at a gas station, Mommy. A gas station!” During a later trip, we rented an apartment in Rome that had a typical Italian elevator, where you could clearly observe the pulleys hoisting the cabin up and down. Located beside the central staircase, the elevator had double swinging doors and a metal grate, all of which had to be carefully closed if we wanted the elevator to move. Leo took charge of “operating” the elevator, eagerly pressing the button to call for it, and then closing the doors once we were aboard. Children naturally unlock experiences, especially in Italy. Once in Florence, we stayed at a friend’s apartment that overlooks a private park belonging to the exclusive Four Seasons Hotel. My friend said we could enter the park, which is studded with period sculptures, just by visiting the café inside. Yet since the hotel was quite swanky, I hesitated when Leo and I arrived at the entrance, giving no thought to his t-shirt, which was emblazoned with the city’s soccer club logo and the team’s signature purple color. But when I asked the doorman, the born-and-bred Florentine looked at Leo’s Fiorentina shirt, and exclaimed, “In that shirt, he can go wherever he wants!” I suspect more compromises are ahead. But what about the payoff? Will he eventually become fluent in Italian? Will he live there as I did, an expat in thrall to the language of Dante (the poet, not the dog)? Only time will tell. For now, he knows the Italian word for cuckold and has a taste for Ferrari merchandise. I can imagine him one day exchanging the quadricycle from the Villa Borghese for a fast Italian car — maybe one that he could use to drive us around our favorite country. None of us would be compromising.