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Things to do in Siena

Itineraries for Your Trip to Siena

Siena locals share their perfect days.
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3 Days in Siena for Families

Curated by Rebecca WinkeItalophile and travel enthusiast who’s lived in Italy for 20-plus years.

With the hills of Chianti to the north and the Val d’Orcia to the south, Siena is ideally located for a Tuscan family escape. After your youngsters have explored the medieval old town's winding streets and wide squares, it’s a quick trip to the surrounding hill towns and countryside for family-friendly adventures, from truffle hunts to scenic walks and bike rides.

Our sons especially loved staying in Siena since the old town is a city-wide scavenger hunt, divided into 17 contrade (neighborhoods) named after animals or objects. We spent our afternoons wandering the back lanes to spot giraffes, snails, unicorns, and other symbols decorating the historic buildings and fountains. Here are my tips for family fun in Siena.

The summer sun in Siena is relentless; plan outdoor activities for early morning and late afternoon.

If you only have time for one thing, make it climbing the Tower of Mangia for bird’s-eye views over the old town and outlying hills.

Day 1

Begin by exploring the medieval cityscape of Siena’s old town with a kid-focused walking tour. Learn about the annual Palio festival, a historic celebration marked by a raucous bareback horse race around the main Piazza del Campo square between riders from the city’s 17 different contrade.

Once you’ve taken in Siena’s highlights, venture beyond the city walls into the surrounding Crete Senesi. This picturesque lunar landscape has gently rolling hills that are ideal for a kid-friendly hike, e-bike ride, horseback excursion, or all-terrain vehicle adventure.

Day 2

Today, head just a few minutes north to the Chianti hills, to explore the tiny hamlets of Greve, Castellina, and Radda in Chianti. Enjoy a scenic drive with tots or explore on foot, by e-bike, or horseback with older kids. Stop for a rustic Tuscan lunch at a farm or winery.

Next, break up the sightseeing with a family-focused cooking class at a Chianti farmhouse. Let your budding chefs get hands-on in a pasta-making lesson, then learn the secrets to making tiramisù and other classic Italian dishes. Relax and enjoy a rustic dinner featuring the dishes your family prepared together.

Day 3

Just south of Siena is the UNESCO-listed hills of the Val d’Orcia, dotted with historic estates where sheep and heirloom Cinta Senese pigs roam. Connect with a local farming family this morning to learn about how the animals are raised and sample artisan pecorino cheese and charcuterie or enjoy a farm-to-table lunch.

In the afternoon, continue to elegant Pienza, one of the most beautiful hill towns in the Val d’Orcia. Take a walk through its tiny Renaissance center, stopping for gelato. Older kids will enjoy a guided tour to learn more about this unique town’s history and architecture.

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