Italian cooking class with kids
Photo©: Anna Fishman / Olegana Travel Boutique
Italians have kids too
“Is there anything to do in Italy with kids? I don’t want them bored in museums and churches.” I hear some version of this almost every month, from parents planning their first trip over and, more and more, from grandparents who want to take the grandchildren somewhere that will stay with them. My answer hasn’t changed in ten years of planning these trips. Italians have kids too, and those kids are not spending their summers in the Uffizi. They’re on farms, in kitchens, in the sea and in the saddle.
Traditional Italian and Tuscan ceramics with colorful, hand-painted designs.
Photo©: Anna Fishman / Olegana Travel Boutique
Tuscany is where I send most families, and not for the reasons the postcards suggest. Yes, the hills look the way you imagine. But what makes it work with children is that almost everything a family wants to do here happens outdoors, with your hands, and ends with something to eat. A cheese farm where the kids milk the sheep. A castle whose dungeon is now the wine cellar. A lake with a boat on it. A beach an hour from the hills that most visitors never find.
This is the Tuscany I build for families: slow mornings, one good thing a day, and an itinerary that works for a six year old, a sixteen year old and the grandparents at the same time. Here’s what that looks like.
The lay of the land for a family
Families do best in Tuscany with one base and short drives, not a new hotel every two nights. The region sorts itself into a few pockets, and I usually pick one and let the days unfold from there.
Enjoying beautiful city views with the kids.
Photo©: Anna Fishman / Olegana Travel Boutique
Chianti and the hills south of Florence. Between Florence and Siena, with the city close enough for a day and the countryside close enough to forget it. Castles turned into wineries, a cashmere goat farm, and San Gimignano’s towers half an hour away. The right choice when the family wants Florence without sleeping in it.
The Val d’Orcia: Montalcino, Pienza and Montepulciano. Further south, quieter, and the most photographed valley in Italy for good reason. This is sheep’s milk cheese country and Brunello country, with hilltop towns small enough to walk end to end with a stroller. My first choice for families with younger children.
Photo©: Anna Fishman / Olegana Travel Boutique
Siena. The medieval city at the center of it all, best done as a day with a guide who knows how to tell the story of the Palio to a ten year old. Children remember the contrade flags and the sweets long after they’ve forgotten the cathedral facade.
Lucca and the hills toward the coast. Walled Lucca is a bicycle town, and twenty minutes away is Collodi, where the author of Pinocchio spent his childhood. Beyond it, the Tuscan coast, which is the part of the region I have to talk families into and never regret.
If you’re comparing this to other Italy Italy itineraries on the site, think of Tuscany as the slow middle chapter: Florence or Rome at either end, and a week of countryside in between where the pace drops and the kids run.
The days worth building the trip around
Over the years I’ve kept a short list of experiences in Tuscany that work for every age at the table. They fall into four kinds of day. A family trip usually gets one or two of each.
Farm days
Enjoying a glass of wine while taking in the vineyard views.
Photo©: Anna Fishman / Olegana Travel Boutique
Start with the animals, because that’s where every child’s face changes. On a family-run estate in Montalcino, the morning is a small-production Brunello tasting for the adults while the vintner walks everyone through the cellar. Then it’s off to an educational farm in the hills where the children follow raw sheep’s milk from the animal to the ricotta, feed and shepherd the heritage breeds, and taste the result from fresh to well aged. Even the smallest ones get the wool, the smell of the barn and the sound of the milking, which is really what they came for.
Photo©: Anna Fishman / Olegana Travel Boutique
In Chianti there’s a cashmere goat farm, the only certified wildlife-friendly farm in Europe, where the kids learn how the fiber is collected and spun and spend most of the visit with their hands in the goats’ coats. Lunch is organic produce from the farmers’ market and cheese from the neighboring herders, and the afternoon is San Gimignano, with its towers to climb and its gelato to argue over.
Outside Pienza, a working organic dairy overlooking the valley does the same for sheep, goats and donkeys, with the farmers explaining the shepherds’ day before you watch the pecorino being formed in the creamery. And for the family that wants something nobody else at school has done, there’s a Brunello estate where, after lunch, an alpaca is waiting for each of you to take for a walk through the countryside.
Days in the kitchen
Family pasta-making and cooking class in Italy.
Photo©: Anna Fishman / Olegana Travel Boutique
The cooking class is the single day families thank me for most, and I’ve written separately about cooking classes in Italy and how I match the teacher to the family. In Tuscany my favorite version is on a thirteenth-century castle estate where the children roll pasta and churn gelato with the chef, the adults get a tasting from the estate’s own production, and everyone sits down on the terrace above the vines to eat what they made. The castle tour in between includes the old underground prison, which is now the wine cellar, and which is the part the kids talk about at dinner.
Photo©: Anna Fishman / Olegana Travel Boutique
Siena gets a food day of its own. A guide walks the family through the alleys with stops for panforte, ricciarelli, pizza by the slice and gelato, telling the city’s story between bites. It’s the best way I know to get a child interested in a Gothic piazza.
Then there is the truffle hunt, which I save for families with dog lovers in them. Two hours in the woods with a hunter and his trained dogs, a snack of what you found at a farmhouse, and a long lunch at a small winery paired with Nobile di Montepulciano. The children usually ask to go back.
Active days
Kids enjoying fun activities together.
Photo©: Anna Fishman / Olegana Travel Boutique
Tuscany is better on horseback than it is from a car window. One of my favorite days starts with a ride through the vineyards and woods, then leaves the horses in the stables for a two-course lunch at a castle in the Montalcino hills. For families with younger riders, I swap the castle for a farm lunch and an afternoon at the pool.
Photo©: Anna Fishman / Olegana Travel Boutique
Montepulciano Lake is one of fourteen nature reserves in the province of Siena and one of the last freshwater wetlands in central Italy. Migratory birds stop here between Europe and Africa, and the family can hike to the birdwatching tower, take a motorboat across the water, and finish at a winery for lunch. It is the quietest day of the trip and often the one the parents remember.
And the beach. Few visitors realize the Tuscan coast is about an hour from most of the hill towns, with long sandy stretches, warm shallow water and almost no one from abroad. I arrange the car, the sunbeds and the umbrellas, and lunch at a seaside restaurant where the kids can walk straight from the table to the water. In July and August this day is what saves the trip from the heat.
Story days
Traditional Venetian cicchetti, small open-faced toasts with assorted toppings.
Photo©: Anna Fishman / Olegana Travel Boutique
Florence with children is a question of editing. A guide who knows which rooms to skip, which workshops will let the kids try something, and where the good pizza is turns an overwhelming city into a day they ask to repeat. I plan it around the children rather than the checklist, and the Renaissance still gets through.
Photo©: Anna Fishman / Olegana Travel Boutique
My favorite story day is Pinocchio’s. A morning inside the walls of Lucca, lunch at a trattoria, then Collodi, where Carlo Lorenzini’s father tended the gardens of a grand villa and his mother kept the rooms. Next door is the park built around the tale, where the children walk the story from the cat and the fox to the blue fairy. Grandparents, in my experience, enjoy this one most of all.
Chianti’s castles make a story day too: a thirteenth-century estate turned winery, a farm lunch of bread from the estate’s own grain and the farm’s own salami, and an afternoon with Tibetan goats, wild boar, donkeys and ducks. Medieval life from the lord’s hall to the farmyard, in one afternoon.
Ready to plan Tuscany with your family?
Tell me who’s coming and what they love, and I’ll build the days around them. Email anna@oleganatravelboutique.com, call (917) 345-5792, or book a planning call.
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“Once we got to our destination, we didn’t have to think about a THING (except where to get our next gelato).”
Kimberly M., Italy
When to go
Enjoying the beautiful spring weather in Italy.
Photo©: Anna Fishman / Olegana Travel Boutique
April to early June. The valley is green, the lambs are on the farms, and the cheese is at its freshest. School schedules make this hard for American families, which is exactly why I push grandparents toward it when the grandchildren are young enough to travel in spring.
Photo©: Anna Fishman / Olegana Travel Boutique
Late June through August. Peak family season, and still my busiest. The trick is to plan around the heat: farms and the lake in the morning, the pool in the afternoon, towns after five. This is when the beach day earns its place.
September and October. The grape harvest, the olive harvest right after, and the truffle season beginning. The light goes gold and the crowds thin. If you can travel with older children or take them out of school for a week, this is the Tuscany I’d choose for my own family, and the reason I keep writing about fall in Europe.
November to March. Quiet and mostly closed in the countryside. I send families to the cities in winter, not the hills.
A week in Tuscany with the family
One base, one good thing a day, and room to do nothing. Here is a shape I return to often, from a restored farmhouse estate in the Val d’Orcia with a pool, a kitchen garden and enough space that the children can roam while the adults sit with a glass of something.
Day 1
Arrive in Florence, private transfer south through the hills, and a slow first evening on the terrace.
Photo©: Anna Fishman / Olegana Travel Boutique
Day 2
Montalcino morning: the Brunello estate for the adults, then the cheese farm where the kids follow milk to ricotta and meet the animals.
Photo©: Anna Fishman / Olegana Travel Boutique
Day 3
Cooking class at the castle. Pasta, gelato, the dungeon cellar, lunch on the terrace, and a long afternoon at the pool
Photo©: Anna Fishman / Olegana Travel Boutique
Day 4
Siena by sweets, with a guide who makes the Palio come alive. Back early for a quiet evening.
Photo©: Anna Fishman / Olegana Travel Boutique
Day 5
Horseback through the vineyards, a farm lunch, and swimming. Or the lake and the birdwatching tower, if the family prefers water to saddles.
Photo©: Anna Fishman / Olegana Travel Boutique
Day 6
Pienza and Montepulciano: the olive oil producer, the dairy with the donkeys, a gelato in the piazza, and a truffle hunt for those who want it.
Photo©: Anna Fishman / Olegana Travel Boutique
Day 7
The coast. Sunbeds, umbrellas, a seaside lunch, and the kind of tired that makes the drive home quiet.
Photo©: Anna Fishman / Olegana Travel Boutique
Day 8
Return to Florence for a guided family day and a pizza and gelato dinner before the flight home, or carry on to Rome by train.
Photo©: Anna Fishman / Olegana Travel Boutique
Add Florence and Rome at either end and you have something close to my Classic Italy itinerary with a family’s week of countryside in the middle.
Who this trip is for
Enjoying a family picnic with the kids in the beautiful Italian spring weather.
Photo©: Anna Fishman / Olegana Travel Boutique
Families with young children. Toddlers to about ten. One base, no early starts, farms and pools every day, and a stroller-friendly town or two. The Val d’Orcia is built for you.
Families with teenagers. Horseback, the truffle dogs, the lake boat and a Florence day with a guide who treats them like adults. Teens come home from Tuscany talking about the cooking class, every time.
Piazza del Duomo in Florence, Italy, featuring the Florence Cathedral and Giotto’s Campanile.
Photo©: Anna Fishman / Olegana Travel Boutique
Grandparents bringing the grandchildren. This is the trip I’m asked about most. A gentler pace, a private driver so nobody is navigating, and days that let three generations do the same thing at their own speed. Pinocchio’s park and the cheese farm are the two I’d never leave out.
Multigenerational groups. Two families or a reunion. A villa or farmhouse estate with separate wings, a private chef for a few of the nights, and experiences chosen so that nobody has to split up.
And when it’s just you and your friends, without the children, the countryside works just as well. That’s what my women’s group trips are for.
Connecting destinations
Traveling by train with the kids to the next destination.
Photo©: Anna Fishman / Olegana Travel Boutique
Tuscany pairs naturally with Florence at the start and Rome at the end, both reachable without a flight. Florence is an hour from most of the hill towns, and Rome is a ninety-minute train from Florence or a two-hour private transfer from the Val d’Orcia, which puts the Colosseum and a golf-cart tour of the city at the end of the week.
Umbria sits directly east and is Tuscany with fewer people: Orvieto, Assisi and the hills around Montefalco add two or three days without changing the pace. For families with older children who want the sea for longer, the Tuscan coast and the islands of the Tuscan archipelago extend the trip west, and Liguria is two hours north for a few days on the Riviera.
For a spring break with younger children, I sometimes suggest comparing this to Portugal with kids, which is a shorter flight and warm earlier in the year. For a summer with grandparents, it’s Tuscany.
Why work with a luxury travel advisor for a family trip
Photo©: Anna Fishman / Olegana Travel Boutique
A family trip to Tuscany has more moving parts than a couple’s trip, and the parts that go wrong are the ones you can’t see from home. The farm that stops taking visitors in August. The cooking class that’s wonderful for adults and tedious for a seven year old. The hilltop town where the car has to stay a kilometer below and the stroller doesn’t.
I’ve stood on these farms, eaten at these tables and watched which experiences hold a child’s attention and which lose it. The suppliers I work with know my families and set up for them: a smaller group, a shorter walk, a kitchen that puts the kids at the front. That’s what you get when you hand the planning to Olegana Travel Boutique instead of a search engine, and it’s why my custom trips for families start with a conversation about the children, not about the hotels.
And when something changes on the ground, a cancelled boat day or a sick child, there’s one person to call who already knows the alternatives.
Anna Fishman, the visionary and soulful force behind Olegana Travel Boutique, orchestrates transformative journeys where meticulously curated adventures meet authentic connection and exquisite, bespoke exploration.
Photo©: Dania Sander / Unique Focus Photography
Ready to plan your family’s trip to Tuscany?
Tell me who’s coming and I’ll take it from there.
Email: anna@oleganatravelboutique.com
Call: (917) 345-5792
Book a planning call
Frequently Asked Questions
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There isn’t a wrong one. Toddlers and young children love the farms and the pools; older children and teenagers get the most out of the truffle hunt, horseback riding and the cooking class. I plan differently for each, so tell me the ages and I’ll build around them.
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One base in the countryside, within an hour of the experiences you care about most. For younger children I lean toward the Val d’Orcia; for families who want Florence in the mix, the Chianti hills. A farmhouse estate or villa with a pool and space to spread out works better than a hotel for most families.
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I almost always arrange a private driver for the experience days and a car only if the family wants independence for the rest. Tuscan roads are narrow, hill towns restrict traffic, and nobody enjoys parking in Siena with children in the back seat.
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July and August are hot, but the itinerary is designed around it: farms, the lake and the towns in the morning, the pool in the afternoon, and at least one beach day on the coast. Families who follow that rhythm have a wonderful time.
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Yes, and many of my Tuscany families are three generations. A private driver, shorter walks, and experiences where everyone can sit when they like, such as the cheese farms, the cooking class and the lake, make it comfortable for everyone.
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A week in the countryside is ideal, with Florence or Rome added at either end if you have the time. Fewer than five days means too much driving and not enough of the slow afternoons that make it work.
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Most families fly into Florence, Rome or Pisa. Seasonal nonstop service from the United States exists on some of these routes, and routes change from year to year, so check with your airline. I handle the transfers from the airport to your base.