Siena (Italy)

The Tuscan town of Siena is one of the most picturesque cities in all of Italy. From its beautiful duomo to its well-known horse race, Siena should definitely be on your must-see list when planning a trip to Italy. We may not be able to travel there this year but hopefully it will reopen to visitors soon. Start planning now for a trip in 2022!


Siena was founded by the Etruscans (see my post about Orvieto for more details about this time period) and was its own republic for four hundred years in the Middle Ages. It’s located in the heart of Tuscany, atop three hills, making it one of the most beautiful and quintessential hill towns of Italy.

View from Siena’s fortified wall

It’s well-known for its expansive Piazza del Campo, where the centuries-old Palio horse race is held twice a year. This race pits ten jockeys from the city’s wards (contrades) against each other in a barebacked, white knuckle race around the piazza. The different contrades have their own colors, flags, and mascots and are very competitive. Watch this excellent BBC video to learn more about the Palio. We visited Siena before the July race in 2016 and our younger son quickly adopted the Lupa (she-wolf) contrade as his favorite – and it won that year, it’s first in decades! He got a Lupa flag, and it really was a special souvenir for him to remember the visit!


Siena is the perfect medium-sized town to make a great home base for travels throughout Tuscany. We visited as a day trip from Florence, but I wish we had stayed at least one night in Siena’s distinctive red-brick homes. 

Most of Siena’s historic city center is a pedestrian-only zone, which makes sight-seeing with children much easier. We hired a private guide through Absolute Italy to ensure a child-friendly walking tour of the city. 

The city is very walkable and there’s much to see. Check out Rick Steves’ walking tour of Siena for a great list of its highlights (click on “listen”). 

The striped duomo is one of the most striking in Italy and dates from the 13th century. We did a quick self-guided tour of the interior, and you don’t want to miss seeing the amazing artwork by Michelangelo and Bernini!

The Il Campo – or large piazza – is very close to the duomo. This piazza is one of the largest and most expansive in all of Italy. This is where the Palio is held – imagine the piazza filled with 60,000 people cheering for horses racing around at break-neck speeds. We were there just a few days before the race and you could feel the energy in the city!

There are several museums in the city but we did not have time to see any of them on our three hour walking tour. They are:

There’s also a 330 foot city tower you can climb (if you can handle the nearly 400 steps!).

Siena is a beautiful little town that should be on everyone’s list to visit while vacationing in Italy. Even small children will be drawn in by its classic charm!

Helpful hints: 

  • Spend at least one night in Siena to see it in the evening after the day trippers have left. That’s on my list for my next visit!
  • There are many hotels and villa rentals available in the area. Also check out the agriturismos – farms where your family can stay and participate in farm life! One of my must-see hotels is near Siena – Castello di Casole. I also recommend utilizing a travel agent specializing in child-friendly accommodations, like Ciao Bambino, to make sure your hotel or home is appropriate for children. 
  • Siena is a sizable town so restaurants are plentiful. It is well-known for its fresh, local cuisine and Chianti and Brunello wines. Children will love the plentiful pizza and pasta meals at the restaurants!
  • Easy day trips from Siena include: Florence, the wine towns of Montalcino and Montepulciano, and the tower-filled town of San Gimignano

Books to Read:

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