Itineraries for Your Trip to Chianti
3 Days in Chianti for Families
Chianti is a natural playground for tots and an adventure park for teens. The tiny villages offer pocket-size piazzas to explore and quiet pedestrian lanes to wander, while the wide Tuscan countryside is great for active families who love hiking, biking, and horseback riding. There are farms to visit, towers to climb, and even truffles to unearth.
This swath of rolling woods, vineyards, and olive groves has long been our family’s country retreat, where my sons have experienced everything from cheesemaking on a dairy farm to horses thundering around Siena’s grand Piazza del Campo for the annual Palio race. Here’s how to show your family the best of Chianti in three days.
Hot summers are no joke; plan outdoor activities for early morning or late afternoon.
If you only have time for one thing, make it Piazza del Campo in Siena where the annual Palio horse race is held.
Begin in Chianti’s heart, where hilltop villages such as Greve, Panzano, Castellina, and Radda in Chianti are ripe for exploring. Drive or village-hop on foot, by e-bike, or on horseback. Most Chianti tours include a farm-to-table lunch at a countryside estate or cellar (with wine tasting for the grown-ups).
This area is the birthplace of Tuscany's rural cuisine, and there’s no better place to take a family-friendly cooking class to learn how to make fresh pasta, tiramisu, and other crowd-pleasers. Join your host and instructor at a local farmhouse for a hands-on class followed by dinner overlooking the hills.
Follow an expert forager and trained pups into the Tuscan woods for a truffle hunt. Kids love watching dogs sniff out black truffles from under the forest floor and learning how the pooches get rewarded (Hint: They don’t eat the truffles!). End with a rustic lunch at a farm-to-table restaurant.
Visit the hill town of San Gimignano on the western border of Chianti to stroll through its medieval old town and climb its highest tower. More than 70 towers once pierced the sky, but now only a dozen still stand. The tallest is Torre Grossa, open to the public.
Turn your sights to Siena, which sits on the far southern reaches of Chianti. This town is famous for its yearly Palio, a historic festival that culminates in a bareback horse race around the main square, Piazza del Campo. Learn about the 17 different contrade (districts) that compete and try to spot their symbols around town.
The landscape around Siena, known as the Crete Senesi, is much different than the lush hills further to the north in Chianti. This afternoon, explore the surrounding countryside with a hike, e-bike ride, horseback excursion, or all-terrain vehicle adventure.
