Tips for Exploring Southern Tuscany with Kids

The beauty of Tuscany will etch a place in your heart, but truly experiencing its rolling hills can feel elusive for families. Although the big gems of Florence, plus neighboring towns such as Pisa and Lucca, make the northern half of Tuscany ideal for a first visit to the region, it’s too far to explore much beyond Siena. For families willing to peel back the layers and enjoy a holiday at a slower pace, a true taste of Tuscan life awaits as you head south.


Southern Tuscany’s enchanting landscape casts a magical effect on a family vacation

What to Do in Southern Tuscany with Kids

The Basics

A car is absolutely necessary to explore this region. Families will find it easiest to choose one southern Tuscan spot to call home and make day trips from there; moving accommodations is a hassle with kids and cuts into vacation time. There will be a good deal of time to relax and recharge in between outings, so it’s critical to stay at a property with amenities that appeal to your family.

Location is of utmost importance, as it will dictate which towns will be most easily accessible and help to prevent excess time in the car. Pick a home base around Siena if you want to explore Chianti and perhaps make a day trip to Florence. If Montalcino, Montepulciano or even a glimpse of Umbria are on your list, stay south of Siena.

TIP: We’re huge fans of Tuscan agriturismos, or farm stays, with kids — virtually all of these properties are fabulous for every age group and allow families to experience the region in an authentic way. For guidance about choosing the right one, start with our post on Essential Tips for a Farm Stay in Tuscany with Kids.


A cooking class is a must in Tuscany with kids

Local Activities

Southern Tuscany is less about the big sights and more about the spaces in between. Sounds enticing, but what will your family actually do?

Much of the appeal of the area can be found in slowing down and savoring the landscape: walks through quaint walled towns; a glass of wine as you take in the scenery while your kids splash in the pool. Stop the car to take pictures of the way the light hits a bale of hay or of the kids smiling against a backdrop of sunflowers that extend farther than the eye can see. Southern Tuscany is also home to the lush, verdant Val d’Orcia, a UNESCO world heritage site and a standout even in a region known for its spectacular natural beauty.

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A family cooking class is a great way to learn from a local and understand how people in the region came to eat as they do. This activity is best for kids over eight, as it is a fairly lengthy process. You will likely prepare (and then enjoy) an entire meal from scratch, including making, rolling out, drying and cooking fresh pasta. Consider classes by Italian grandma Nonna Ciana, conducted in a specially designed kitchen on her family’s property near Siena. Many agriturismi can also arrange for cooking classes and cheese or wine tastings.


Podere Il Casale. Photos by Lisa Frederick

For younger kids, a visit to a working farm is usually a big hit. One good bet is Podere Il Casale outside Pienza — parents will love tasting the wine, cheese, honey and other edibles made onsite as much as little ones enjoy seeing the barnyard animals.

Kids aren’t quick to ooh and ahh over the landscape, but they’re captivated by games. Parents can organize a simple scavenger hunt and let the kids explore their environs. They’ll be thrilled to find figs, olives or a sprig of lavender, and the game will allow them to connect with Tuscany in a tangible way. Older kids might enjoy taking a camera along and doing a photo scavenger hunt.

TIP: Ciao Bambino Family Vacation Consultants can connect you with incredible local resources who craft one-of-a-kind, authentically Tuscan experiences for your trip. Click here to request more information.


Ancient Tuscan hill towns such as Montalcino are compact enough for kids to wander while parents marvel at the views

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Must-See Towns


Siena is one of the largest dots on the Tuscan landscape and offers plenty to keep everyone amused. Siena is home to the famed Il Palio horse race, run twice annually in the town’s central Piazza del Campo. Visiting Siena during Il Palio (early July and again in mid-August) isn’t necessarily a family-friendly endeavor because of the intense crowds, but you can soak up the atmosphere any time of year. Grab a drink at one of the cafes on Piazza del Campo or stroll the streets and do some window-shopping. Gelato will tempt you around almost every corner, but Venchi is a favorite.


The first medieval walls of Montalcino were built in the 13th century, and its impressive fortress will greet you as you approach. The center of town is like a postcard, complete with its pretty cathedral; convenient parking is found just outside the city walls. There are also many restaurants, making it a good dining spot for those staying nearby. Make sure to stop at Il Grifo for thin-crust pizza — everyone in your family will be glad you did.


The adorable walled town of Pienza will bowl you over with its charm. It isn’t overrun with tourists and is small enough to enjoy in a few hours: a swing by the church, a few locally owned shops, views of the hillside and, of course, the obligatory gelato stop. The ambiance and lighting here are particularly special — you’ll take drool-worthy photos that you’ll cherish for years.


It has been said that if a Tuscan town is too easy, too eager to be liked, it is not properly Tuscan. If this is the case, then Montepulciano is as Tuscan as it gets. Be prepared for walking, as Montepulciano has some fairly steep hills, but the reward is that it looks and feels much as it has since the late 1500s. The views are tremendous, and parents will appreciate a glass of the namesake Vino Nobile di Montepulciano.


Tucked in the heart of the Val d’Orcia, a bit off the beaten tourist path, is the little gem that is Monticchiello. Though tiny, this village is beautifully preserved and evocative — not to mention, it’s home to one of our favorite restaurants in Tuscany: Osteria la Porta. A meal here is worth the detour in and of itself.

San Casciano dei Bagni

The ancient spa town of San Casciano dei Bagni, which lies near the Umbrian border, is worth a visit for its natural hot springs, a draw since Roman times. It boasts a surprising array of restaurants for its size, including the excellent Ristorante Daniela.

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Relevant Links:

Browse all family-friendly accommodations and things to do in Tuscany on Ciao Bambino

Essential tips for a farm stay in Tuscany with kids

Things to do in Siena with kids

Best Tuscan hill towns with kids: I heart Pienza

Editor’s Note: Photos by Amy Andrews except where noted.

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