- 1 Siena – Capital of the Province
- 2 Castellina
- 3 Castiglione d'Orcia
- 4 Chianciano Terme
- 5 Lecchi in Chianti
- 6 Montalcino
- 7 Montepulciano - Hilltop town known for its wine.
- 8 Monteriggioni
- 9 Pienza
- 10 Rapolano Terme
- 11 San Gimignano
- 1 Bagno Vignoni
- 2 Bagni San Filippo
- 3 Chiusure
- Castelmuzio A small charming town, worth a visit.
- 4 Radicondoli
- 5 Radda In Chianti
- 6 San Quirico d'Orcia
- 7 Valiano
- 8 Montefollonico
There are many charming places to visit in the Province of Siena. If you have limited time, the city of Siena is the highlight, and you can easily take 3-5 days to see all the sights there if you so desire. However, if you have more than a few days, make sure to go to San Gimignano, if nowhere else. It's much smaller in area and population than Siena and, with its towers and panoramic view over the countryside, gives the visitor a different experience of a walled Medieval city. Also, because of its small area, a reasonably able bodied person can walk from one end of San Gimignano to the other in 20 minutes, and while it has fewer and smaller attractions than Siena, they are of great quality. Pienza is of special interest to fans of Gothic architecture, because it was completely redesigned as a Gothic village in honor of native son Pope Pius II in the 15th century. If a beautiful rustic monastery with frescoes by Michelangelo's teacher appeals to you, go to the Abbey of Monte Oliveto Maggiore in the tiny village of Chiusure.
- 1 Duomo di Siena . Siena's magnificent black and white Italian Romanesque cathedral includes the Libreria Piccolomini, with splendid frescoes by Pinturicchio, the lovely Baptistery (separate entrance and charge), and an attached museum (separate entrance and charge, see below). Also marvel at the inlaid floors; even as they are sometimes covered for protection, a section is always left visible. At the height of Siena's power it was decided to enlarge the cathedral so that the existing Duomo would become merely its transept; the money ran out very soon after one of the new outer walls, which is still standing as a reminder of the grandiose undertaking, was completed. It is possible to see all of this in one day, but expect it to take at least the better part of an afternoon.
- 2 Palazzo Pubblico . This striking structure has functioned as Siena's City Hall for almost 800 years and is probably the building that most recognizably represents Siena. It contains (among many other things) the famous frescoes on good and bad government by Ambrogio Lorenzetti, frescoes by Simone Martini and Duccio, and access to the Torre del Mangia, from the top of which you can view a beautiful panorama of the Sienese countryside. The frescoes on good and bad government and their effects on the city and surrounding countryside (painted 1338-1339), probably Ambrogio Lorenzetti's greatest masterpieces, are in the Sala dei Nove, where the Council of Nine who ruled the city state in the early 14th century could see them and, it was hoped, would keep them close to mind while making important decisions. These frescoes and Duccio's Maestà in the Museo dell'Opera del Duomo are the most important paintings in Siena and for many people represent highlights of a visit to this city, but there are many other beautiful things to see in the Palazzo Pubblico, so allow some time (preferably a couple of hours) to view them all. This building's exterior is equally beautiful and includes a lovely marble chapel, the Cappella di Piazza, which is at the foot of the Torre di Mangia. Built in 1352, it is dedicated to the Virgin Mary, as was the entire city after it avoided annihilation in the devastating black plague of 1348.
- 3 Basilica Cateriniana San Domenico . This large, austere Gothic basilica (usually simply called San Domenico) is not only dedicated to St. Catherine of Siena, along with St. Dominic, but was frequented by her and contains a period portrait of her by Andrea Vanni and relics including her head. It also features several other works by Sienese Gothic painters and impressively high vaulted ceilings. It is quite close to the long-distance bus stop, so if you are going to or from Siena by bus and have the time even to briefly enter this house of prayer, do.
- 4 Abbey of Sant'Antimo . Ancient and still functioning Benedictine abbey. The abbey dates to at least the 9th century.
- 5 San Biagio Church . A wonderful Renaissance church with soaring nave & dome, with a challenging walk from the church to the town centre.
- 6 Santa Maria della Scala . This medieval hospital, now a museum, is chock-full of medieval art including altarpieces by Bartolommeo Bulgarini and frescoes by the Lorenzetti brothers and Simone Martini. Also part of the complex (no additional admission charge) is the Museo Archeologico Nazionale, which exhibits some important archeological finds from the area, plus items from public and private collections of antiquities that are mostly from Siena and Chiusi.
- 7 Fonte Gaia . The fountain sculpted in 1419 by the great Sienese sculptor, Jacopo della Quercia, is a focal point of the piazza. The remains of the original sculptures can be viewed in the loggia of the Palazzo Pubblico (see above), but the appearance of the fountain, composed of copies made in 1858, is not bad and remains a major sight in this city.
- 8 Pinacoteca Nazionale di Siena . The Pinacoteca is full of Sienese paintings from the city's Medieval heyday.
- 9 Museo dell'Opera del Duomo . This museum includes the famous Maestà by Duccio and many other great works by Sienese masters. After you've seen all the art, you can also treat yourself to a beautiful panorama from Il Facciatone, the tower in this building. The view is about as good as the one from the Torre del Mangia in the Palazzo Pubblico but somewhat different, although if you are rushed for time, pick one tower to climb (either one).
It can be very difficult finding a good restaurant open between the hours of about 14:00 to 19:00.
Vegetarians and vegans should have no problem eating in Siena as staff at Italian restaurants tend to be very accommodating. Try ribollita, a regional specialty vegetable soup. 100 percent vegan and delicious. Pizza in Italy (and authentic Italian restaurants elsewhere) has no dairy products or eggs in the dough.
This is Chianti wine country. You will have no trouble finding well-priced Chianti wines in supermercati or trattorie.
Florence - short bus or train journey from Siena.
Rome - Possible day trip to get a glimpse of Italy's capital. Bus or train from Siena.