Best Tuscan Hill Towns with Kids: I Heart Pienza

Pienza Val D'Orcia Italy with Kids

Boys and Tuscan hill towns, a match made in heaven

There’s no shortage of spectacular villages in Tuscany. When it comes to choosing the best Tuscan hill towns to visit with kids, I recommend prioritizing those with the biggest bang in a small area so logistics and walking are minimized. Located in the heart of the Unesco-protected Val D’Orcia region, Pienza tops my favorite list and we revisit this architectural gem whenever we are in the area. Here’s why:

Why Pienza is a Favorite Tuscan Hill Town with Kids

Pienza Tuscany Pecorino Cheese Shop

Pienza is known for Pecorino cheese with tasting opportunities galore

Pecorino Cheese Galore

Italian cheese lovers take note, the Pecorino cheese produced in and around Pienza is to die for. Cheese shops line the streets of this village and there are abundant opportunities to taste all styles of Pecorino. Sold fresh, medium-aged and mature, trying before buying is a treat and a fun group activity for all ages. Kids love getting in on the action; we voted for our favorites in each shop and loved indulging in them each night with honey and fig jam. Delightful!

Pienza Italy Well

Plenty of kid-friendly nuggets to explore within this small village

Kid-Friendly Streets and Sights

If you look up idyllic Tuscan village in the dictionary, it may just have a picture of Pienza as the photo. Boasting one of the finest examples of Renaissance architecture in Italy, Pienza is visual perfection for parents. Meanwhile, the mostly car-free streets are safe for kid-friendly loitering, plus there are just enough interesting things to explore like this historic well to keep restless bodies entertained.

It’s small enough that you can spend an hour and a half here and feel complete before heading off to lunch. A perfect half-day excursion for families.

View of Pienza from Montichiello

Looking back at Pienza from the hamlet of Montichiello

Lunch for the Italy Meal Memory Book

There are a number of fantastic places to dine in Pienza, but we always return to the magificent Osteria La Porta in the nearby hamlet of Monticchiello (10-minute drive from Pienza). Honestly, I’ve eaten extraordinary meals in practically every region in Italy, but Osteria La Porta never fails to please. The simple, homemade pastas and seasonal fare is consistently tremendous. It’s well-priced and they will make special meals for kids when requested. In good weather, sit on the terrace with stunning views looking back at Pienza.

Getting to Pienza

Pienza is more or less a 40-minute drive from the main A1 highway running through Tuscany (unless you are Italian; in that case it’s a 20-minute drive). It’s a good day trip for those staying as far north as Siena or as far south as Orvieto. Otherwise, I adore staying in the part of Tuscany. It’s quiet are more arid than staying in and around Florence, but the pristine landscape with zero urban sprawl is what makes this area so magical. It’s a true escape from day-to-day stress and modern inconvenience. Ciao Bambino recommended La Foce, La Bandita, and Hotel Adler-Thermae are all a 20-minute drive from Pienza.

Photos by Amie O’Shaughnessy

Relevant Links:

Ciao Bambino recommended family accommodations in Italy

52 things to know before traveling to Italy with kids

Essential tips for a farm stay in Tuscany with kids

The ultimate Italy villa rental with kids

Kid-friendly tour guides in Italy 

Context Travel family program in Florence

Gladiator School in Rome

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