What my kids taught me about traveling in Tuscany

Traveling with a two-year-old is parenting on hard mode. You don't have your routines, your support, or the baby doll she drags around the house. Dining out is living on the edge. And how do you explain why we're going into another cathedral? But somewhere between the third gelato meltdown and the fifth playground, Tuscany starts to feel less like a destination and more like a place we're actually inhabiting, however briefly.

It happens in Siena, a medieval town in central Italy. We're at a tree-covered, narrow playground stretched out between the mud-colored bricks of a residential area. My two kids, William and Maggie, aged five and two, are chasing each other around, darting between the gaps of a climbing dome. My wife, Danielle, and I sit on a bench, resting from a day of carrying or corralling them across the cobblestone streets. High up, laundry flutters in the breeze. Another family shows up with their 4- or 5-year-old daughter, pink bows in her hair. My kids, completely absorbed in their sibling game of chase, pay the newcomer no attention.

We've wandered another Tuscan town superficially, unable to linger in museums or peer at the architectural marvels around us because of the kids' brief attention spans. Look at all this beauty! I want to say to them, Imagine the horse race that happens every year in Piazza del Campo. Look at all this art made before tablets, the Internet, cars! They don't care. They want playgrounds. And watching them, I notice the laundry again, fluttering in the breeze beneath apartment windows. We're not in tourist Siena. We're where people live – where kids play after school and families hang their clothes out to dry. 

We've been in Tuscany a few days now, and this has become our routine: self-catered breakfast at the agriturismo (farm-stay accommodation) – oatmeal, with the usual request of raisins and peanut butter – and then a long winding drive to whatever destination we plan to explore. Sometimes we make it back for naps, sometimes we power through the day and the frayed emotion a napless afternoon brings.

Siena is, of course, a tourist town like a dozen other tourist towns in Tuscany. At each town – San Gimignano, Orvieto, Volterra – I'm struck both by the beauty and the artifice. The shops selling wine or olive oil or chocolate. The tour guides waving tiny flags on tall sticks and the throngs of their followers. I find myself looking for laundry, a signal that yes, people live here, and you're not just visiting a theme park.

Truffle hunting

I have mixed feelings about the truffle hunt. I've always been curious – what kind of dog? How rare are truffles anyway? – but I could leave the fungal delicacy, which always tastes to me like a cross between dirt and body odor.

Ilya, the truffle hunter, greets us in the lobby of the agriturismo. Another family has lingered – two adults, three kids – and when he greets them, too, I realize they're joining. A group tour.

Ilya's long, dark curly hair is tied back with a hairband, wavy locks spilling out. His septum is pierced, and he wears cargo pants and hiking boots. "Today we will find truffles!" he announces.

We head out to the restaurant terraces overlooking the Tuscan hillside. A tractor sows a field, and birds follow it like a cloud. Ilya appears with hot chocolates for the kids and espressos for the adults. He launches into a briefing – mycelium networks, his grandmother who also hunted truffles in these hills – while the kids occupy themselves with pastries.

Then he leads us to a small, '90s-era white Fiat Panda and opens the door. Out pops a small, wiry-haired, black and white dog. "This is Nura," Ilya says. Maggie, strapped to Danielle in a toddler carrier she's barely able to fit in, kicks her feet with glee, and Danielle lowers her to join the petting frenzy as Nura darts between everyone's legs, her tail wagging furiously.

Ilya then gives a command in Italian, and Nura darts into the nearby woods. "You'd better follow her!" The hunt has begun. The children are down the tree-covered hill first, following the small dog as she zig-zags across the forest floor, nose to the ground, tail up. Within seconds, Nura's digging.

Ilya runs over and searches the dirt. "Look! Start digging!" he says. The kids all drive their hands into the soil, spreading it around with their fingers. One of them holds up what looks like a rock – Ilya wipes the dirt off and stands, gives it a whiff. A truffle.

The group passes the tiny mushroom around, each of us sniffing it. Maggie, still not sure how to "sniff," only wiggles her nose. To William, it's the worst thing he can imagine. He will not smell any of the other truffles we find, and asks to ensure that no truffle touches any of his food while we're in Italy. My boy.

For the next hour and a half, we follow Nura through the forest. She miraculously finds four, each a little smaller than a golf ball, but the kids couldn’t care less about the fungus. They just want to chase the dog.

Visiting Pisa and Lucca

Finding a parking spot in Pisa is hard, and it's putting me on edge. It's the first Italian city I've driven in, and the large Audi SUV rental feels like driving a dump truck through the narrow European avenues. We find a large paid lot a few blocks from Piazza del Duomo and use the nearby toilets, which cost €1 we don't have, but the attendant takes pity on us.

Danielle and I are all business. The kids are having a moment, and I'd pressed for an earlier stop and photo op on the way to Pisa. Danielle, always wise, said that the stop would destabilize the day's delicately balanced plan of Pisa, then Lucca, then back to the agriturismo for dinner. The photo op was a letdown, and I, ego too bruised to admit Danielle was right, have defaulted to silence and terse answers to logistical questions.

We shuffle the kids through the souvenir market set up just outside the piazza – the Tower of Pisa miniatures too alluring for child eyes – and successfully get them inside without needing to take home another knick-knack.

The piazza is just shy of slammed, but we can see the view. The trio of buildings – the baptistery, the cathedral and the famous leaning tower – spread out across a lush green lawn are, to put it mildly, incredible. In the low morning sun, they seem to be carved from marble, a mass of arches and peaks and columns and shadows. We wander through the cathedral, peer up at its ornate ceilings and admire the walls covered in Romanesque art.

We snap the obligatory family photo in front of the leaning tower, or the "Falling Tower" as Maggie has taken to calling it. Visitors are permitted to go up the tower, but not children, due to the lean. We pick a street at random and head off in search of lunch.

We settle on one of the several dining areas with al fresco eating. Everyone seems to be on edge. The little busy bags of crayons and stickers Danielle and I bring along for the kids don't seem to have the same allure. I'm waiting for one of them to embarrass us in front of the other diners of Pisa. Luckily, the meal passes without incident, which is the best we can hope for.

Lucca is a 20-minute drive northeast, and by the time we find parking inside the old city walls, the mood has shifted. It's quieter here, tree-covered. William and Maggie are refreshed from a power nap in the back of the Audi, and Danielle has forgiven me for the photo stop.

Lucca is for wandering. Pinpointing ourselves in the Lonely Planet guidebook, we make a plan to stroll through the old city, and then climb the city walls for the walk back. The city is markedly less touristed – there are still groups of tourists and sneaker-clad, camera-toting visitors (including yours truly) – but the volume is turned down. The kids run after pigeons, and I'm not worried they'll run into anyone.

We grab snacks at a small market (a real market!) – a small loaf of bread that Danielle tears apart and distributes with the fairness of a matriarch, and some olives the kids decide they don't want. We wander quietly, Maggie back in the toddler carrier, her red sneakers dangling.

Another cathedral. William has been to more cathedrals this trip than he's been in churches his entire life. And it's here that he begins asking questions – "What are those pictures for?" "Why is the ceiling so high?" I try to explain the Christian god and religion generally in hushed tones while he studies ornate floors and arched ceilings. I'm not sure if we're raising a future art historian or if he was just tired of chasing pigeons, but I'll take it.

At the other end of Lucca's old town, we find another playground at the base of the city walls. It's a Saturday afternoon, and the playground is active. It's also a little worn, with chunks of wood falling off the climbing frame. Our kids do a few circuits – the slide is operational, as are the swings – before finding a flock of pigeons to terrorize. Danielle and I sit on a bench in the shade, the morning's tension gone.

We walk back along the city walls, a nice leafy stroll with views of the dense old town on the right and the more modern exterior on the left. Walkers and runners pass by, tourists on bikes teeter over the paved path. On the side of one of the buildings in the old town, I can spot laundry fluttering in the breeze.

At the agriturismo

We make it back to Agriturismo Biologico Diacceroni as dusk is falling. The roads there are windy and narrow, and the hills are lavender in the fading light. Just outside our apartment, there's a small playground, and I watch the kids bump into each other and trip over holes in the ground while Danielle cooks the pasta we'd bought from a market somewhere between Lucca and the agriturismo.

The stars come out, and in the darkness of the Tuscan hills, they're more visible than they are back home; the hint of the Milky Way is stamped across the inky black. I try to get the kids to look up. "See the stars? We don't get those at home," I tell them. They briefly look at the sky before going back to the dimly lit playground, giggling in the dark.

I keep wondering whether this was all worth it, whether the discomfort of long-haul travel (William would get carsick on the drive back to the airport and throw up all over the back seat) and fights over photo ops or where to have lunch are worth the cost. There's a better, more brightly lit playground a block from our house.

I think about all those tourist towns – Orvieto and San Gimignano and even Pisa. There’s real depth there, centuries of history we only skimmed because the kids couldn’t sit still long enough to see it. But they led us somewhere else – residential playgrounds, quiet markets, the parts of each town off the typical tourist trail.

Danielle has finished cooking, and I hustle the kids inside. We each take our seats and eat like we do back home, talking about our day, the falling tower, the pigeons and the pictures. After dinner, we get the kids to bed and finish a bottle of wine. I clean up dinner and a final chore: hang our laundry out to dry.

Make it happen

When to visit

We went in mid-October, and the timing was ideal. The summer crowds had thinned, the weather was warm but not scorching, and the hills had that classic golden, just-tilled look. With young children, avoiding peak summer also means shorter lines and fewer meltdowns in crowded piazzas. The tradeoff: the agriturismo pool was too chilly for swimming, much to the dismay of both kids.

Where to stay

An agriturismo is the move if you’re traveling with little ones. Ours – Agriturismo Biologico Diacceroni, located in the hills outside Volterra – had several playgrounds, pizza nights, pony rides, and enough space that the kids could run around without bothering anyone. Self-catering meals meant we could stick to familiar breakfast routines and avoid the stress of restaurant dinners when everyone was tired. The drives to hilltop towns were 30–60 minutes along beautiful, winding roads. Book activities, like truffle hunting or cooking classes, in advance.

Getting around

Rent a car. The hilltop towns aren’t well-connected by public transport, and you’ll want flexibility to bail when nap time calls. Italian drivers tailgate and signal loosely, but the roads are manageable – just expect tight parking situations. Paid parking lots at the base of each hill town are your friend, but be prepared for a steep walk.

What I wish I knew before

Leave the stroller in the car. The hilltop towns are steep and cobblestoned, and you’ll spend more time wrestling it up steps than actually using it. A toddler carrier was essential for Maggie. Also, if your kids are prone to motion sickness, those winding Tuscan roads plus screen time is a bad combo – William made it most of the trip before losing his lunch on the drive back to Rome. Keep the iPads for flat highways only. Playgrounds are easy to find, usually shaded, and often tucked at the base of old city walls or near a quiet park. Finding them became our strategy for a successful family day.