Montalcino is atop a hill south of Siena, off of the SS2, about a 45 minute drive. Approaching from the north, take a turnoff from the SS2 just south of Buonconvento. Take the road up to the Traversa di Monti.
From the south or east, you arrive via San Quirico d’Orcia or Grosetto. From Grosetto cut off at Paganico and then follow the signs. You will pass by Sant’Angelo in Scalo on your way. This approach takes you through some pretty huge vineyards. From San Quirico, head towards Torrenieri and then take the Traversa di Monte up the hill to Montalcino.
Parking in Montalcino
In any case, go to the traffic circle at the top of the hill and then look for parking. If you are arriving for the first time, I suggest parking outside the walls in either the new lot or the old lot. Once you have the lay of the land, try the free spaces or metered across from or behind the Fortezza.
From Buonconvento or San Quirico, you will arrive at a new traffic circle with lavender light posts and a new gas station. The caffe at the gas station has surprisingly good caffe and decent, really cheap food.
If you are coming from either Buonconvento or San Quirico, you will pass the Porta Cerbaia. (I don’t recommend going in the Porta Cerbaia the first few times you come to town. It is very convenient, but tight.) Pass the town (with the walls on your right) until you come to a traffic circle with a large mosaic. The mosaic was done by a famous artist who is the owner of Castello di Romitorio winery. The mosaic is considered either a great piece of public art (the city government’s view), a billboard for Castello di Romitorio or a public eyesore. I have threatened to knock it down many a time but Kay says I shouldn’t. Most of my winery owner friends would like it if I did so. This is the most important crossroad in the area as it leads to St Antimo, San Angelo or Buonconvento/San Quirico.
The new lot is to the right and the older lot is down the hill. If you go into the town, there is a pay lot across from the Fortezza. The drive to this lot continues and more pay parking is available by the soccer field behind the Fortezza. But locals and those in the know always try for the spaces on the unpaved area beyond the second lot. They are free and surprisingly available. In any case, park and enter the town by the Fortezza. There is a large bronze map which will help you get oriented. From there, walk down make for the Piazza di Popolo first. The Piazza is the hub of Montalcino and most of my descriptions are written as walks starting from the Piazza di Popolo.
The Town of Montalcino
Montalcino is a walled city that rose to fame in the wars between Siena and Florence (Firenze). The Sienese republic abandoned their town and retreated to Montalcino. Firenze attacked and the city was under siege. The Firenzens won the seige and instead of destrying the town physically, they suppressed it economically. Montalcino was an unimportant backwater until after the Risorgimento and the founding of the modern tradition of Brunello wine by the Biondi Santi Family in the 1880s. The result is that the many practices that other regions have had to over come (such as blending of inferior grapes as in Chianti) were never a part of the tradition of Brunello. On the other hand, the tradition of Brunello is very new and as such, even today 100 years later there are many schools of thought on making the wine.
The heart of Montalcino is the Piazza del Popolo. It is at the base of the clock tower. You cannot miss it. There are two logge which are used for public events or just sitting and enjoying life.
Heading downhill from Piazza del Popolo is Via Mazzini, a pedestrianized street with many little shops. At the bottom of the street is Piazza Cavour with a little parking and then a main parking lot behind the municipal building.
Heading up from Piazza del Popolo, you have two choices, up a steep incline to the Piazza Garibaldi or along a level street, Via Matteotti, home to a number of my favorite shops and favorite places to hang out and drink and eat in Montalcino. From Garibaldi, you can go up a steep hill to another piazza complete with 1600s fortress and parking, Piazzalle Fortezza.
Piazza del Popolo
A few highlights here include Bar alle Logge and Fiaschetteria Italiana, two of the best bars in Montalcino. Bar alle Logge is on V Matteotti and draws a little hipper and younger crowd. We only go to Fiaschetteria when Logge is closed. Both have superb espresso and cappuccino.
Bar alle Logge has a wider wine selection in terms of having a nice selection of non Montalcino wines. It is a great wine bar. In the early evening, it will be crowded with people stopping in after work. Many of them will be drinking cocktails instead of wine. They put out a great spread of food at the cocktail hour. You can also sit down outdoors, paying a lot more for your drinks, and get served. They will make up a plate of snacks for you. They also have a short menu of food, good for a mid afternoon snack or a rainy day sit. We are in Bar alle Logge three or four times a day when we stay in Montalcino.
Osticcio is just up the street from Bar alle Logge. It is a superb, serious wine shop and enoteca with food. You can have a nice tasting of Brunello along with incredible meats and cheeses. The view from the tables in the back is stupendous. They close early so its really a lunch or mid afternoon kind of place.
The nameless meat shop is on the opposite side of the street from Bar alle Logge and Osticcio. It is a super meat shop where everything is cut to order. Specialties include lamb and pork. Stefano, the late owner, was a regular at Bar alle Logge after his shop closed. We heard he died in a motorcycle accident but the shop lives on with his spirit hovering over the pandemonium!
The vegetable shop, up a little farther, is a great place. The original couple who ran it have retired, but it is still the best place to buy veggies in town. The other main choice is the Coop (supermarket)!
Lambardi is a great bakery. I think Via Matteoti changes names by the time you reach Lambardi.
Also along this same block are Giglio and Il Re di Macchia. I now prefer the food at Giglio but both are pretty fantastic. They both offer traditional foods raised up a bit, with attention paid to the raw ingredients. Both have great wine choices available. Il Re di Macchia is a little more straightforward in its cooking, Giglio is a little more refined. We have had great pinci al ragu di cinghiale, a nice rabbit salad and superb pork at Il Re de Macchia (plus very good wines by the glass). Giglio has really good desserts (my chef ate four by himself at one dinner) and the food is more refined. I recall really liking a stuffed pasta there. If we are in town a week, we would probably eat at both one time each.
In the other direction from the Piazza del Popolo, heading downhill on Via Mazzini, isPierangelini, our favorite in-town wine shop. They are really friendly and have a good selection.
Further down the street is a favorite restaurant, Taverna del Grappolo Blu. It is a superb place to eat. The food is good and plentiful and flavorful. The owner is active in the historical pageants of Montalcino. The wine list is okay with some smaller wineries represented. I always have a good time there.
Also down this street are some of Montalcino’s best art shops. Just a few of my favorites include MontalcinoArte, owned by Simone Pinori. He is a great artist in his own right, using a load of different techniques in oil to great effect. We have an olive oil grove that pays homage to Van Gogh in style, as well as some pointillist paintings. He also represents a fabulous quilt maker, Lydia Barilla from Cortona. She makes museum quality art. We have two of her works in our restaurant and they command incredible attention.
Another great art store is Angolo di Terracotta. They have two outlets but we prefer this one.
Also on this stretch of Via Mazzini is a butcher shop that specializes in Chianina beef for Fiorentina and in Cinta Sinese. However, the butcher is not as popular with my Montalcinese friends so I always feel a little like a traitor going in there. But I do.Montalcino 412 is a new store with great picnic supplies. You can also find superb cottons and linens and nice olive wood stuff in this area as well.
Piazza Cavour
At the bottom of V Mazzini is a little garden with benches and a fountain: Piazza Cavour. There are always people just hanging out there. I love to sit for a while and just drink in the scene. Off to the side is a municipal building with some displays of art in its courtyard and incredible views. Note that there is a parking lot behind this building that often has spaces when the other lots are full (like on market day). Al Giardino restaurant is on the square. While we have heard good things about it, our meal there was pretty bad. Maybe an off night.
Piazza Garibaldi
When you are sitting in Piazza Garibaldi, there are two roads that head uphill besides Via Mazzini. Both are worth walking. The one to the right skirts the edge of town and has some grassy bits off to the right. It leads to Madonna del Soccoroso and from there back to the Fortezza.
Back at Piazza del Popolo, you can go up a little pedestrian alleyway to Piazza Garibaldi. The Popolo will be to your left. Piazza Garibaldi has several wine shops but I rarely buy from them. There is a new restaurant (Le Potazzine?) which we have yet to try. Our favorite stop off Garibaldi is Perche No?, the gelato shop. WONDERFUL!
Off of the Piazza are some steep stairs that head towards the art gallery of the church. It is located in a restored building. The collection is very nice, with a lot of impressive pieces (especially the small crucifix by Giambologna, a few pieces by one or both of the Lorenzetti’s. But more noteworthy than any individual piece is the museum itself. It was restored so well. As you go thru it, you get peeks into later rooms that tease your eye. The scale of it is human and the art well spaced out and placed.
Piazzale Fortezza
Piazzale Fortezza is home to our favorite enoteca, Enoteca Fortezza in the Fortezza itself. There are multiple reasons to visit. First off is the wine tasting available. They always have a bunch of wines available. There is a Cruvinet machine with six or so super premium wines (at high prices) as well as a dozen or more wines on the counter.
Angelina is one of the managers and she is wonderful. She is also the font of all knowledge when it comes to restaurants. I never go out to dinner without consulting her. Allesandro is also a manager and he is always busy with packing wines to ship or with organizing tastings. In addition to the great wines, they also make plates of cheese and meats to go along with your tasting. There are tables inside or out for your use.
Several times a year, the Fortezza is home to various festivals. The most famous of which is the Festa del Tondo in October. But I have also been there in April when there was a fundraiser for the local soccer team which was a great excuse for eating outdoors. You can also explore the Fortezza which is a treat in itself. For a small fee you can climb up to the ramparts for perhaps the best view of the Val d’Orcia around! The second floor often had art on exhibit as well.
Outside the Fortezza are several wine shops, the best of which is Enoteca Franciwith the same owners as the Fortezza. There are a couple of restaurants of note,Porta al Cassero and Sciame. Porta al Cassero is an old fashioned place with large portions of heavy and good food. Sometimes the food is a little lax and sometimes its pretty good. In any case, it is very traditional and cheap. I love the tongue with salsa verde. I have not tried Sciame, but other folk I trust love it.
Santuario della Madonno del Soccoroso
From the Fortezza you can walk down in the direction of a larger park and a shopping area. The Coop (supermarket) and the lavanderia (laundry) are in this area. So is the Poste (Post Office). Following along the walls you get to Santuario della Madonno del Soccoroso and more incredible views. From here you can continue back down to Piazza Cavour.
The Duomo is also in the area. There are some steps you can take to get to it (at least there were but the last time I looked there was construction connected with the building of a new parking lot). The Duomo has incredible artifacts from long ago, including an alter that is probably 1000 years old. But overall the Duomo is not especially wonderful.
Last but not least is the wine shop Bruno Dalmazio below the Porta Cerbaia on the road to San Quirico, the Traversa del Monte. They have a great selection of the wines from Montalcino and the rest of Toscana, Umbria and then parts south. They also have two computer terminals which you can use free of charge. The folks there are very nice, the selection very large and well thought out, the pricing fair. They have those self service wine dispensing machines but they have never been working when I have been to the shop. Maybe someday! They also have a great selection of big bottles.