While you’re in the Siena area, you’ll want to make a side trip to Montalcino. Montalcino is a walled hilltop town in Tuscany that has wonderful views of the surrounding valleys.
Located 27 miles south of Siena, Montalcino is where the famous Brunello di Montalcino and Rosso di Montalcino wines are made. It’s a small town and you can get there from Siena by bus. It takes 60 to 90 minutes on the bus and costs only about four Euros one way.
Montalcino is located to the west of Pienza, close to the Crete Senesi in Val d’Orcia. It is 42 km from Siena, 110 km from Florence and 150 km from Pisa. The Monte Amiata is located nearby.
I first learned about Montalcino from the delightful and informative book Vanilla Beans & Brodo: Real Life in the Hills of Tuscany. When I finally got to visit Montalcino in person, it was a real thrill to see the streets and restaurants that author Isabella Dusi described so evocatively in her memoir.
When you’re in Montalcino, make sure you see the 14th Century fortezza, and drop in to the Enoteca la Fortezza wine-tasting shop which is located under the fort. The Enoteca is a great place to sample the local Brunello and Rosso wines (phone 0577-849211). You can get a variety of Tuscan wines by the glass for about four Euros each. Since you’re there, you’ve got to sample the regional Brunello, which is about seven or eight Euros for a glass. They’ll serve it with plates of savory local cheeses so you can have lunch there.
Another great place in Montalcino for wine tasting is the Piazza del Popolo (phone 0577-849043). When you get to the Piazza del Popolo, find the Caffe Fiaschetteria Italiana No. 6. Check out the days. It can be closed on Monday and Tuesday, I’ve heard. You can get a wine tasting there with three or four varieties of Brunello to choose from, ranging from about four Euros on up to well over ten Euros a glass.
Also in Montalcino, check out the small civic museum, which has a really nice collection of Sienese paintings ranging from the 1400’s to the Renaissance. A few years ago the Civic Museum moved its collection to a new home at the former St. Augustine Monastery on Via Ricasoli 31 (phone 0577-846014). It’ll cost you about five Euros and it’s open Tuesday through Sunday.
Another thing to see in Montalcino is the 12th Century Cistercian Abbey of Sant’Antimo, which is about ten kilometers south of Montalcino. It’s one of Tuscany’s most beautiful, intact Romanesque churches. An extra special experience is if you time your visit to coincide with the Gregorian chants that are performed daily by the monks that still live there.
There’s a tourist office in Montalcino that you can check with for the hours the chants are going to be performed.


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I was there 2 years ago and just loved it. It is a small town (village, really) but very interesting and picturesque. Be prepared to walk up steep hills.
I think this is the town or village from “Under the Tuscan Sun?” My brother went there and liked it so much that he became interested in a medieval property for sale in this historical village. Unfortunately for me he did not buy it!
Hi Mike,
Actually, the town described in the book “Under the Tuscan Sun” by Frances Mayes is Cortona. It’s not far from Montalcino (about a 40 minute drive) and is indeed a very beautiful medieval town. Both towns are well worth visiting.