Siena is one of Tuscany’s most popular hill towns and although it’s also the biggest, it’s still possible to see the top sights in one day. Siena is best known for its Palio horse-race, run twice in summer around the large main square known as il Campo. With about 4 miles of walls surrounding the historic center, there’s lots to see and do and it makes a good base for visiting the Chianti wine country and other hill towns. But if you’re visiting Siena on a day trip or only want to spend one night, this itinerary takes you to the highlights in just one day.
Start your visit at the Basilica of San Domenico, on the edge of the historic center and pedestrian zone. From the side of the church, you’ll have a nice view of Siena’s cathedral and the town. Founded by the Dominicans in 1226, this was the church attended by Saint Catherine as she grew up nearby in Siena. When she was canonized her relics were transferred here, including her head (called the Holy or Sacred head) which you can see in the altar dedicated to Saint Catherine and a finger, but her tomb is in Rome.
From Piazza San Domenico, take Via della Spienza to walk into the historic center. The street has several shops selling typical Tuscan products. Turn right when you get to Via dei Banchi, the street of Bankers. Siena was developed by bankers and money lenders during the middle ages and Monte dei Paschi, the world’s oldest bank still in operation, was built in 1472 in Piazza Salimbeni, where you’ll see several other stately Renaissance and Gothic buildings.
Via dei Banchi was part of the pilgrimage route from Canterbury to Rome when Siena was a major stop along the route. Today Via dei Banchi is one of the main shopping streets. Stop in at Nannini to try the Ricciarelli, typical cookies of Siena, or Panforte, the traditional cake with almonds, dried fruit, and spices that dates from the 13th century. Nannini is also a good place to stop for a gelato.
As you walk along the streets of Siena, look up to see animal figures on the corners. These represent the contrada, or neighborhood. Siena is divided into 17 contrade and most of them have an animal name. For example the goose, or oca, is the contrada that has won the most palio races and dragon is the contrada where Saint Catherine grew up, close to the first church you visited.
At Vicolo San Pietro, you’ll see the medieval building where business was conducted. Take the steps down into the big open space, Piazza del Campo, Siena’s main square, more commonly called il Campo. The piazza has an unusual fan shape and a beautiful fountain, Fonte Gaia, that’s a reproduction of the original 15th century fountain.
Originally the site of the Roman forum, it was the main market square in the middle ages and in summer the ring around the square becomes the track for the horse race, a competition with medieval origins in which each neighborhood tries to win the palio, or banner, given to the contrada that wins the race.
On the square is the town hall, Palazzo Publico, and the tall medieval bell tower, Torre del Mangia. You can climb to the 505 steps to the top of the tower for great views but the climb is not for the faint of heart, there’s an easier view spot that we’ll see later. Around the piazza are shops, restaurants, and bars.
Just up the hill from Il Campo is Piazza del Duomo where you’ll see Siena’s beautiful black-and-white-striped 13th century cathedral. You can buy tickets for the duomo and other monuments or an Opa Si Pass, good for 3 days at the ticket office on the square. If you have time, the combo pass is the best option as all the monuments are worth seeing and it also includes access to the panoramic terrace.
Inside the Duomo are statues and art works created by top Renaissance artists including Michelangelo, Donatello, and Bernini. Two things not to miss are the inlaid wood choir and the 13th century pulpit by Nicola Pisano. Be sure to visit the Piccolomini Library, covered with frescoes by Pinturicchio.
One of the top sights is the duomo floor with 56 inlaid marble panels which are only unveiled for a short period each year. Parts of the cathedral’s upper floors are open as part of a special tour, called the Gate of Heaven or Secret Itineraries Tour, definitely worth seeing. Find out more about the Duomo floor panels and Gate of Heaven tour or buy a Cathedral Combo Plus Pass that includes the tour.
The other monuments included with the combination pass are Saint John’s Baptistery, the Cathedral Crypt, Cathedral museum, and the panoramic terrace of the Facciatone, the building that was planned to be a new cathedral but was never completed. From the terrace you’ll have great views of Siena and the valley without having to climb the winding stone staircase of the Torre Mangia.
The cathedral and monuments are normally open from 10:30 until 7:00 PM (may close earlier in winter), except on Sunday when the cathedral is only open from 1:30 to 6:00 PM. Check Siena Cathedral web site for current hours and more visiting information.
End your day back in the main square with an apertivo at Osteria Liberamente, a great place to sit and enjoy piazza life and watch the sunset.
Take a Guided Tour: Siena Duomo and City Walking Tour, a 2 hour guided tour of the cathedral and top sights in the historic center with an English speaking guide.
Take a Cooking Class: Tuscan Cooking Class, a 4 hour hands-on cooking class with food and wine.
Take an Excursion: Chianti and Castle Tour, a 5 hour small-group tour to two Tuscan wineries and the medieval hill town of Monteriggioni.