
5 lessons from traveling to Italy with kids
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5 lessons from traveling to Italy with kids: Parenting Unfiltered
My family and I traveled to Tuscany for 11 days. It was also my kids’ first trip overseas and our longest family vacation to date. Here’s what I learned about family travel. What have you learned? Tell me in the comments. The trip was full of logistics. It’s possible to be too organized. Sometimes, familiarity works. Your plans might fall through, and that can be a blessing. We were out a bunch of money and left with nothing to do for four hours. We set for my kids by the sidewalk with a group of tourists and ended up freaking out on the throngs of tourists. We stood on the plaza in 98-degree heat, gazing at the architectural marvels, wondering what to do next. The next day, we ate at Sergio Gozzi, which is a cramped, but delightful lunch spot in San Lorenzo Square. We went to San Lorenzo, known for hand-scrawled menus touting tripe in tomato sauce and tongue in New York City.
Usually, we go to Maine for a week every summer: a quick car ride, with very few logistics. This trip was full of logistics. Here’s what I learned. What have you learned about family travel? Tell me in the comments.
Last week, my family and I traveled to Tuscany for 11 days. This was a big deal, not just because our side foray to Venice coincided with the Bezos-Sánchez wedding . It was also my kids’ first trip overseas and our longest family vacation to date. I wanted to seize the moment before our middle-schooler morphed into a standoffish teen but once our 8-year-old was mature enough to appreciate Michelangelo’s David. (OK, that didn’t happen. He wanted to know why he was naked. But we tried.)
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Kids will be anxious about surprising stuff. I expected them to be nervous about the long flight (I was!) or about not knowing the language (our flirtations with the handy Duolingo language app be damned). But when Andy, my 8th-grader, crawled into our bed on the first night at our Tuscan Vrbo, I was surprised: He hadn’t done that for years. Turns out he was afraid to be in a new house — remote and up a windy road, to boot — and didn’t want to let us out of his sight. Buddy! He wanted to know the Italian version of 911; he wanted to see our location on a map; and he wanted us to promise not to go anywhere without him. And I’d been worrying about neck pillows and melatonin.
It’s possible to be too organized. This applies to overpacking an itinerary and to stuffing a suitcase. The handy travel cubes I snagged to streamline suitcases? Totally worth it: They enabled me to pack more stuff and to have a built-in laundry bag to separate dirty clothes (essential with two boys). The cute toiletry bottles recommended by a friend? Complete disaster, because I was too rushed to label them. Jet-lagged and far from my familiar bathroom, I doused my contact lenses in bath gel and nearly blinded myself for a day. Usually, I just buy travel-sized toiletries from CVS. Definitely doing that next time. Sometimes, familiarity works.
Your plans might fall through, and that can be a blessing. I’d meticulously planned a day trip to Florence, where we’d take in Michelangelo’s famous works at The Galleria dell’Accademia and go on a private, nonrefundable tour of the iconic Dome of Florence Cathedral, a Renaissance masterpiece and international landmark.
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This was a fiasco. First, our train into the city was late. (Public transport is essential and generally efficient; you cannot easily drive in Florence due to limited traffic zones.) Then came an unexpected bathroom detour. We were five minutes late for our tour, by which time the guide had departed with our group. I set a poor example for my kids by freaking out on the sidewalk amid throngs of tourists and, ultimately, we were out a bunch of money and left with nothing to do for four hours. We stood on the plaza in 98-degree heat, gazing at the architectural marvel, wondering what to do next.
But our empty schedule meant that we suddenly had time to eat at Trattoria Sergio Gozzi, which was absolutely delightful. This is a cramped, famous lunch spot in San Lorenzo Square frequented by locals, known for hand-scrawled menus touting tripe in tomato sauce and tongue. (Think New York City’s Katz’s Delicatessen, but in Italy.) The servers were so friendly. They were delighted that Peter wanted to try beef tongue. We didn’t speak the language, but we were united by a kindness that offset my rage. And when Pete said “Grazie,” our wizened waiter grinned and patted him on the head. It was an unexpected highlight. Sometimes, canceled plans hide a reward.
Humanity is universal. We live in a scary world. I spend most days at my laptop, working while doom-scrolling issues that make me worry for the planet — and for my kids. But exploring a small sliver of that planet with those kids was reassuring because of the personal interactions that reminded me how, on an individual level, so many people are wonderful: the cheerful chap who sold my son a Celtics jersey in Venice. (Yes, Andy bought a Boston souvenir in the City of Canals.) The nice lady who taught us how to ride a rickety, canopied four-person bike along the walls of Lucca (awkward, tiring, and I didn’t pedal — but she was patient). The waiter at La Cantina Di Miky on the water in Cinque Terre who presented Peter with teriyaki octopus, and the proud look on his face when he ate it. The stranger who lent me a few Euros so I could pay for a public bathroom in Florence. The smiley guy at baggage claim in New York City who said “welcome back” as our bedraggled crew arrived at JFK Airport on the other end.
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We’re home now: adjusting to jet lag, relishing air conditioning (not tons of that in Italy), and doing the amount of laundry that comes with being far from home. But the world seems smaller now. I like that feeling. I hope my kids remember it, too.
Kara Baskin can be reached at kara.baskin@globe.com. Follow her @kcbaskin.
Source: https://www.bostonglobe.com/2025/07/04/lifestyle/5-lessons-traveling-italy-kids/