When people hear “Tuscany,” they picture romantic vineyards, leisurely dinners, and quiet hilltop villages.When you’re traveling Tuscany with four kids, though? Let’s just say the romance looks a little different. It’s a little more like spilled gelato, backseat squabbles, and a constant search for bathrooms. But oh, it’s so worth it…with wine!
Here’s everything I wish I’d known before bringing my small traveling circus to Italy’s dreamiest region, and a peek into one of our most unforgettable family trips yet.
Where to Stay in Tuscany with Kids
Our stay included a five-course farm-to-table Italian dinner one evening, which was truly unforgettable. The nights were cool and breezy, perfect for outdoor dining under twinkling lights. The staff even offered soft blankets so we could linger longer while the kids played Red Rover with new friends near the vineyards.
And yes, there was unlimited wine in our room (a detail every parent deserves to know).
The resort grounds were peaceful yet full of family-friendly adventure from exploring the gardens to splashing in the pool. Nearby, you’ll find wineries, truffle hunting, and horseback riding, all within a short drive.
Horseback Riding in Tuscany: A Family Highlight
One of our most spontaneous and memorable moments was discovering Tuscany Horse Trekking, a charming, family-run farm that offers horseback rides through the vineyards.
They welcomed us like old friends, letting the kids feed goats and chickens while my husband, Angelo, and I sipped a glass of local wine. Then we saddled up and rode through the rolling vineyards with the sun dipping behind the hills.
It was surreal. A true pinch-me experience that felt like it belonged in a movie, but it was just us, in Tuscany, living it.
Family Dinner in Pienza: Where “Gladiator” Was Filmed
For dinner one night, we ventured to La Terrazza del Chiostro in Pienza, the exact spot where Gladiator was filmed! The view over the Val d’Orcia valley was jaw-dropping, and the food was just as stunning.
It’s upscale but the outside terrace was family-welcoming and perfect for when you want to enjoy a truly special Italian meal without worrying about side-eye from fellow diners. The kids loved it (Fanta helps), and we lingered until the sky turned pink and gold.
Best Things to Do in Southern Tuscany with Kids
Explore Pienza Itself
Piazza Pio II & the Duomo: A beautiful, walkable square that feels straight out of a postcard.
Palazzo Piccolomini & Gardens: A quick cultural stop with sweeping views.
Walk the City Walls of Pienza: The best place for photos, stroller-friendly, and free.
Monticchiello: A nearby medieval village with charm, views, and great coffee.
Podere il Casale: A working farm where kids can meet animals, taste cheese, or even join a cooking class.
San Quirico d’Orcia: Stroll the gardens, grab gelato, and drive the iconic cypress-lined roads nearby.
Monastery of Sant’Anna in Camprena: Quiet, scenic, and peaceful — perfect for an easy family stop.
Vineyard Picnics: Some wineries in Val d’Orcia offer kid-friendly walks and picnic setups.
Bike or E-Bike Tours: Gentle hills, incredible views, and plenty of snack stops.
Truffle Hunting: Many local farms offer seasonal hunts and the kids love the dogs!
Real Talk: Traveling Tuscany with Kids
There were meltdowns, sure. But there were also moments that stopped time: my kids riding horses through vineyards, giggling over shared gelato, saying “grazie” to strangers, and discovering that travel can feel like home, even far away.
You’ll leave tired, a little sunburned, but completely in love with Italy. If you’ve been dreaming of bringing your family to Tuscany, do it.
Find the family suites
Room for everyone to rest and recharge every evening.
Always bring swimsuits
You’ll find water everywhere from pools, springs, to lakes.
Plan downtime
The magic happens when you don’t plan every moment.
Rent a car
Public transportation is limited in rural Tuscany and you’ll want the freedom to explore hidden gems.
Download My 3-Day Tuscany Itinerary with Kids!
