Destinations

A Roman Holiday (for Four)

A traveler considers the timeless pleasures of Italy — and the need to reset expectations when seeing the world with kids in tow.

Looking out over Rome
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“WE ARE ALL pilgrims who seek Italy,” Goethe wrote upon his return to chilly Germany following two years spent basking in the warmth of the Mediterranean sun. It’s a line I scribbled in the margins of a journal when I was in my 20s and living in Paris. If there is a city in the world more beautiful than Paris, I don’t know what it is. It is especially stunning at night in the rain — which is good, because you get to see it that way a lot. The summers are glorious, but the rest of the seasons? It rains all the time, and in winter it’s dark by 4 p.m. During the years I lived there, I often longed to escape the cold, the drizzle, the low, gray sky so relentless it has a name (la grisaille). Which is how I discovered Italy.

The first time I stepped foot in Italy, I took a train down to San Remo with my boyfriend and a friend, where we spent Easter weekend in a gloriously faded resort hotel with a saltwater pool designed by Gio Ponti. Our friend, who would later become godfather to my youngest daughter, played a piano concert to an audience of two (us), and as the music echoed through the empty public sitting room, I felt like I was in a Fitzgerald story. The trip was short, and ended with a train strike (we were returning to France, after all). But despite a rattling 10-plus-hour drive back over the Alps in a janky rental car with a sticky manual transmission and a tinny radio that picked up more fuzz than stations, I was completely and unquestionably hooked.

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After that, I returned to Italy every time I could. My boyfriend and I went to Sorrento, where we ate homemade spaghetti vongole at a tiny restaurant overlooking the marina, and lay out with the Italian tourists on bleached rocks, the violent crash of the waves deterring not a single person from sunbathing — except the friend we traveled with, who lay in the shade in tight black jeans. At night we strolled through the streets eating gelato, with that same friend joking he couldn’t tell which of the cute boys he was checking out were gay because they were all so well coiffed and also all holding hands.

I spent one of the most memorable days of my life in Venice during the opening of the Biennale, where I ate a dinner of a brick of foie gras, which my host casually mentioned was a gift from a countess, delivered that morning from her farm. The windows of the apartment overlooking the Grand Canal were thrown open and the wind swept through the room, causing the candlelight to dance. I rented a house with friends one summer in the hills outside of Florence, and another year, one set in the olive groves outside of Castelvetrano. I swam in the grottos of Capri the morning of my wedding; on another trip I took a ferry past the island where Homer was exiled, to visit Favignana. We then took a smaller boat, rowed by a fisherman, around the island, which is surrounded by a bright, white rock that bounces the sunlight back up through the water, causing it to glow an otherworldly blue. Once, I even traveled to Modena for the opening of an artist whose work was collected by the Ferrari family, and got to tag along on a private tour of their factory — something I thought I wouldn’t care about, but have since found myself thinking of with awe every time I have seen one of the cars. I worked in fashion during these years, so I also traveled to Milan more times than I care to count. (My thoughts on Milan? Not my favorite place in Italy, but still Italy.)

Toward the end of my 20s I left Europe and returned to New York, and though Paris has remained a second home for me in the years since, Italy has remained something else. “Italy is the best country in the world,” I say with conviction to friends who are planning trips, to Italians I meet, to anyone who has expressed any semblance of interest in my opinion. My line may not be as lyrical as Goethe’s, but it carries the same sentiment. And who would make a case otherwise, really? The food, the landscapes, the people — what’s not to love? Not to mention that as a New Yorker, it’s a place I find culturally familiar on a visceral level, what with all the talking with hands.

One of the most delightful things I have found about having children is getting to share with them the experiences and places that have been meaningful in my life. Traveling is my greatest pleasure, and traveling with my kids has been an ongoing joy — except, of course, for that pesky global pandemic. My youngest daughter was three when Covid hit. Although she had traveled widely as a baby, we spent so little time outside of our house for the better part of two years that she didn’t remember, ever, being on an airplane. The first time we took her on one again, this past winter, she had such a big meltdown during a layover that we had to corral her into a corner of the airport and let her continue her tantrum at full volume until she had worn herself out. I watched in horror as fellow passengers took out their phones to casually film her screams, and prayed she didn’t wind up going viral on TikTok.

Somehow, though, we got up the courage to travel with her again. And I couldn’t think of anywhere I wanted to go more than Italy.


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Landing in Rome in early April felt like the scene in “The Wizard of Oz” where Dorothy flings open the door to a new world of technicolor. Still cold in New York, in the Italian capital the wisteria were in full bloom, along with the red bud trees and everything else around the city, giving the feeling of being inside a verdant, botanical dream. We arrived the morning of my younger daughter’s fifth birthday. Our hotel greeted us with balloons and chocolates in the room; we celebrated with a cake at each meal we had that day. Blowing out her third set of candles, her joy was undiminished as she smiled at the cries of “Aguri!” being shouted our way from the surrounding diners. (She was a delight on the plane, by the way, connecting so deeply with a stewardess that, several months later, she still mentions her by name from time to time.)

My daughters trooped through the streets of Rome, clocking upwards of 15,000 steps a day without complaint like the tough little city kids they are. They rode the small train through the Villa Borghese, found the drains in the floor of the Pantheon, and ate pasta and mountains of gelato, of course, several times a day. At night, they slept heavily, sharing a bed that the five-year-old declared looked like it belonged to a princess. In Venice they gazed into the windows at all the delicate glassware, completed a scavenger-hunt walk of the city where they found 127 winged lions, and actually, unimaginably, listened to the guide in the boat tour we took explain the history of what we were seeing, including the etymology of the word “ghetto.” They also jumped for hours on the trampoline on the grounds of our hotel, and somehow, magically, made it through a course at a Michelin-starred restaurant. The dinner was an invitation from the hotel that I couldn’t turn down, though I breathed a huge sigh of relief when they headed back to the room after eating their pasta to watch a movie — my husband and I were able to actually enjoy our meal.

Our last stop was an agriturismo in Tuscany. It was the week after Easter, and the property was filled with European families who could have been stand-ins for ours, with some minor linguistic substitutions. There were numerous children the same age as my daughters, and the lack of a single shared language was no deterrent to finding their way to play. In the evenings the children tumbled in and out of the restaurant in small packs, as the parents had long, easy dinners. One boy a little bigger than my younger daughter followed her inside, holding her hand.

“What’s your friend’s name?” I asked her. “Oh, Mommy,” she said, “he doesn’t speak English. Only German.” He tugged her hand and they ran back out to play as the evening mist settled over the valleys of Chianti.

When I first had children, I had to relearn my nomenclature around travel. Previously I took vacations. The word conjures ideas of rest, relaxation, pause. But with young children, that is not the reality. “It’s best,” someone told me when my first daughter was born, “to stop calling them vacations. Think of them as trips.”

That change in language was wildly helpful. It totally reset my expectations for the experience. No longer was I embarking on travels with children with any delusions that it would be restful (a ridiculous notion, if you think about it — is there any single thing about having children that is restful?). But after setting aside the (now completely unattainable) travels of my youth, there was still all sorts of space to have adventures with my family.

Everything I love most about Italy was amplified by my trip there with my children. Most notable for me was the proliferation of warmth, coming from a place with no shortage of it to begin with. My experience of Latin countries, generally, is that the deep value placed on family makes them wonderful places to visit with kids, a theory only reinforced by our little tour of Italy this spring. Smiles from grandfathers on the street, an indulgent extra scoop of gelato for the little one, a special tour for the kids to come into the kitchen to meet the chef — all sorts of everyday kindnesses that we experienced again and again. I also found inspiration in the local family dynamics I observed; as I watched numerous teenage girls walk down the street holding hands with their mothers, I hoped, prayed, that my tween daughter might still be willing to hold my hand in a few years.

Maybe we’ll have to move to Italy to encourage her.

Where to Stay and What to Do When Traveling in Italy With Your Kids in Tow

Departures Executive Editor Skye Parrott shares her top picks.

Where We Stayed

  • Hotel Eden, Rome

    This historic hotel is housed in a nineteenth-century building right off the Villa Borghese, with a rooftop restaurant that overlooks all of Rome. We stayed in adjoining rooms connected by a living area, creating a suite significantly bigger than many apartments I have lived in over the years. Breakfast was a particular hit with my kids, alongside the tour of the kitchen they were given by Marco, one of the waiters. They also loved the tiny slippers and robes provided in each of their sizes. There is a spa on the property (which I didn’t get to go to), as well as a Michelin-starred restaurant, La Terrazza by Chef Fabio Ciervo (which I didn’t get to eat at either). Despite those exclusions, my visit here with my family was one of the nicest stays I’ve ever had, anywhere, due to the level of service and genuine warmth of the generous staff.

  • JW Marriott, Venice

    Located on an island that formerly housed a hospital, this hotel is set away from the bustle of the city center, accessible by half-hourly ferry service to Piazza San Marco. I found the space and respite particularly welcome in a destination as busy as Venice. The rooms are located in an eclectic mix of buildings, and options for families range from regular hotel rooms to bi-level, loft-like suites, and even a private villa. The property is geared toward families; my kids enjoyed being able to run unattended on the grounds, jumping on the trampoline set up outside the breakfast restaurant. They also especially loved the kids club, which is open daily. The hotel also offers what they call a “Chic-nic,” which we had on Easter. Set up among the olive groves, it was truly the most extravagant and chic picnic I have ever seen, and it provided us not just with lunch, but dinner too. There is a spa on the property (which I didn’t go to), and several restaurants, including Fiola at Dopolavoro Venezia by Michelin-starred chef Fabio Trabocchi. The food was amazing, but my recommendation would be to leave the kids behind to truly enjoy this particular meal.

  • Villa Lena, Toiano, Tuscany

    This sprawling property on over 120 acres features several apartments that are set up for families, as well as rooms that can be joined to create family-friendly suites. With two pools and a restaurant that serves breakfast, lunch, and dinner, the property is completely self-contained, though it is also an easy jumping-off point for exploration of the tiny villages dotted through the nearby hills. The hotel is home to an expansive artist-residency program, with the artists providing cultural programming for guests. Programming changes based on the current artists-in-residence, and can range from wild-herb foraging excursions and stained-glass-making classes to morning yoga classes set on an open terrace (by this point you may not be shocked to hear me say, I didn’t get to do these; they overlapped with breakfast). In the summertime and during school holidays, there is also a morning kids’ camp available. While it wasn’t in session when we were there, my children had no trouble making friends with the many other kids running around the property, with whom they swam in the unheated pool and played pétanque, while the parents enjoyed leisurely meals.

  • Hotel Eden, Rome

    This historic hotel is housed in a nineteenth-century building right off the Villa Borghese, with a rooftop restaurant that overlooks all of Rome. We stayed in adjoining rooms connected by a living area, creating a suite significantly bigger than many apartments I have lived in over the years. Breakfast was a particular hit with my kids, alongside the tour of the kitchen they were given by Marco, one of the waiters. They also loved the tiny slippers and robes provided in each of their sizes. There is a spa on the property (which I didn’t get to go to), as well as a Michelin-starred restaurant, La Terrazza by Chef Fabio Ciervo (which I didn’t get to eat at either). Despite those exclusions, my visit here with my family was one of the nicest stays I’ve ever had, anywhere, due to the level of service and genuine warmth of the generous staff.

  • Villa Lena, Toiano, Tuscany

    This sprawling property on over 120 acres features several apartments that are set up for families, as well as rooms that can be joined to create family-friendly suites. With two pools and a restaurant that serves breakfast, lunch, and dinner, the property is completely self-contained, though it is also an easy jumping-off point for exploration of the tiny villages dotted through the nearby hills. The hotel is home to an expansive artist-residency program, with the artists providing cultural programming for guests. Programming changes based on the current artists-in-residence, and can range from wild-herb foraging excursions and stained-glass-making classes to morning yoga classes set on an open terrace (by this point you may not be shocked to hear me say, I didn’t get to do these; they overlapped with breakfast). In the summertime and during school holidays, there is also a morning kids’ camp available. While it wasn’t in session when we were there, my children had no trouble making friends with the many other kids running around the property, with whom they swam in the unheated pool and played pétanque, while the parents enjoyed leisurely meals.

  • JW Marriott, Venice

    Located on an island that formerly housed a hospital, this hotel is set away from the bustle of the city center, accessible by half-hourly ferry service to Piazza San Marco. I found the space and respite particularly welcome in a destination as busy as Venice. The rooms are located in an eclectic mix of buildings, and options for families range from regular hotel rooms to bi-level, loft-like suites, and even a private villa. The property is geared toward families; my kids enjoyed being able to run unattended on the grounds, jumping on the trampoline set up outside the breakfast restaurant. They also especially loved the kids club, which is open daily. The hotel also offers what they call a “Chic-nic,” which we had on Easter. Set up among the olive groves, it was truly the most extravagant and chic picnic I have ever seen, and it provided us not just with lunch, but dinner too. There is a spa on the property (which I didn’t go to), and several restaurants, including Fiola at Dopolavoro Venezia by Michelin-starred chef Fabio Trabocchi. The food was amazing, but my recommendation would be to leave the kids behind to truly enjoy this particular meal.

What We Did

  • Villa Borghese, Rome

    No secret here: This is a great park. With its numerous offerings for kids, including a good playground, a carousel, pedal-bike rentals, and a mini train that circles the perimeter, mine would have happily spent our whole trip here.

  • Gatti di Roma, Rome

    One of my kids’ favorite experiences in Rome was visiting Gatti di Roma, the cat sanctuary located within the Torre Argentina archaeological site. The organization provides health care and shelter to feral cats, and its shelter houses blind, paralyzed, and otherwise disabled cats, who my children enjoyed playing with for well over an hour.

  • Bartolucci, Rome

    This family-owned store, operating since 1936, enchanted my kids with its toys, clocks, music boxes, and Pinocchios, all handmade out of wood.

  • Tours in Venice

    Venice feels to me like a fairy tale, a place that shouldn’t exist. But understanding the fascinating history of why it does makes the experience of visiting that much more enthralling. We did two tours while there: one by boat, which included the smaller canals and residential areas; and one by foot, which was organized as a scavenger hunt for the kids. Both were terrific, and were organized through ShoMe Venice Tours.

  • Villa Borghese, Rome

    No secret here: This is a great park. With its numerous offerings for kids, including a good playground, a carousel, pedal-bike rentals, and a mini train that circles the perimeter, mine would have happily spent our whole trip here.

  • Bartolucci, Rome

    This family-owned store, operating since 1936, enchanted my kids with its toys, clocks, music boxes, and Pinocchios, all handmade out of wood.

  • Gatti di Roma, Rome

    One of my kids’ favorite experiences in Rome was visiting Gatti di Roma, the cat sanctuary located within the Torre Argentina archaeological site. The organization provides health care and shelter to feral cats, and its shelter houses blind, paralyzed, and otherwise disabled cats, who my children enjoyed playing with for well over an hour.

  • Tours in Venice

    Venice feels to me like a fairy tale, a place that shouldn’t exist. But understanding the fascinating history of why it does makes the experience of visiting that much more enthralling. We did two tours while there: one by boat, which included the smaller canals and residential areas; and one by foot, which was organized as a scavenger hunt for the kids. Both were terrific, and were organized through ShoMe Venice Tours.

Getting Around

  • Trains and Volvos

    Trains are one of my favorite things about traveling in Europe, and my kids love the experience too. But trains don’t go everywhere, and I must admit that as an American, with car culture running through my blood, I’m never entirely sorry when a destination requires a drive, as our visit to Tuscany did. I have written before about my love for Volvos, and on this trip we drove an XC90, the same car we have at home — though this one was much newer with a hybrid engine.

  • Trains and Volvos

    Trains are one of my favorite things about traveling in Europe, and my kids love the experience too. But trains don’t go everywhere, and I must admit that as an American, with car culture running through my blood, I’m never entirely sorry when a destination requires a drive, as our visit to Tuscany did. I have written before about my love for Volvos, and on this trip we drove an XC90, the same car we have at home — though this one was much newer with a hybrid engine.

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Our Contributors

Skye Parrott Writer

Skye Parrott is the executive editor of Departures. A magazine editor, photographer, writer, and creative consultant, she was previously a founder of the arts and culture journal Dossier, and editor in chief for the relaunch of Playgirl as a modern, feminist publication.

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