Siena is — in its “a little bit country, a little bit rock-n-roll” way — the perfect Tuscany town to visit with kids. Its historic center (much of it pedestrian) is big enough to offer a mix of bustling shop-lined thoroughfares and picturesque medieval side streets to explore, yet small enough to be easily visited on foot in a day. With wide-open spaces where younger travelers can blow off a bit of steam, fabulous artwork to satisfy their more staid older siblings, and a historic festival with enough pomp and revelry to satisfy everyone, Siena should be on every family’s Tuscan itinerary.
Best Tips for Visiting Siena with Kids
Although Siena does have a small children’s playground in the historic center (on Vicolo della Fortuna), there’s no need to look farther than the town’s famed Piazza del Campo for a recess break. This vast, shell-shaped public square generally teems with tourists soaking up the sun, kids kicking around soccer balls and tight klatches of locals avidly discussing the day’s gossip. With the added bonus of pigeons just begging to be chased and a number of cafes ringing the square, where parents can relax with a cappuccino while keeping an eye on the chasing, this is one of the most picturesque “playgrounds” in Tuscany.
If you have aspiring kings and queens among you, another fabulously Sienese monument-now-playground is the Medici Fortress, located slightly outside of the old town and with a beautiful view over the historic center. The wide outer walls, topped with shaded, bench-lined walking paths, and the original brick ramparts at the rectangular fortress’ four corners make for an excellent play space with a bit of culture thrown in.
The Enoteca Italiana is located in the fortress as well, just in case the grown-ups are interested in a bit of wine tasting and purchasing while the kids play.
Artistic Teaching Moments
Even kids who profess to be “churched out” will be amazed by the incredible inlaid floors in Siena’s Duomo. Kept covered by protective carpets for most of the year, the eye-popping marble panels are revealed once a year (usually from August to October), and their intricate biblical and allegorical scenes stretch across the entire cathedral interior.
These are best seen with a guide (Ciao Bambino recommends vetted guides as part of their Family Vacation Planning Service), whose explanations can make the tableaux come to life for both kids and parents. The most spectacular way to view the floor is from the dizzying heights of the gallery, by booking the Porta del Cielo tour directly at the Duomo.
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Tuscany’s Biggest Party
Siena is perhaps best known for its raucous Palio, a medieval festival and horse race held each year on July 2 and August 16. With a bit of careful planning, attending the Palio can be one of the most memorable adventures your family can have in Italy. I strongly discourage any visitor from showing up blind on the day of the Palio race, however, as the crowd crush and general mayhem can be overwhelming for anyone, but especially for kids.
The most rewarding way to participate in the Palio is through a Palio-themed day tour customized specifically for families. These tours give context to the event by explaining the city’s history — including the 17 rival neighborhoods (contrade) that compete — and give your family the opportunity to experience the Palio as participants rather than mere spectators by including you in the pre-race contrade banquets, having you meet the horses and their jockeys, and arranging for you to watch the race itself from the best vantage points in the piazza.
If you’d rather not book a day tour, there are still ways to make the Palio enjoyable for your family. To avoid the worst of the crowds, consider attending the pre-race trials (prove) held each morning and evening during the three days prior to the race itself. Make sure you’ve aligned yourselves with a contrada and have picked up a scarf (fazzoletto), sold virtually everywhere during the week of the Palio, with its colors to don.
If you are set on seeing the Palio itself, consider purchasing bleacher seats (trying to see the race above the crowd is tough for kids). You’ll have a bird’s-eye view of the race and the pre-race pageantry, including costumed processions and flag-throwing demonstrations.
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Editor’s Note: Rebecca Winke is an innkeeper, blogger and travel writer. She moved to Italy from Chicago in 1993 and shortly thereafter opened an agriturismo at the foot of Mount Subasio near Assisi, Umbria. She spends her time taking care of guests at Brigolante, writing about the lovely region she now calls home at her blog Rebecca’s Ruminations and for Umbria on the Blog, and wondering what strange winds blew an urban vegetarian to a farm in Umbria.