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Southern Tuscany Travel Guide

Montalcino is in the center of one of the most beautiful areas I have ever been to. We love to take half and full day trips from our base of Montalcino. Below are five day trips we have taken. But this only scratches the surface. You can easily travel them on a TCI map of Toscana (Tuscany). They are between half day and a full day. The individual elements are shown below and can be combined variously. The details of the towns and things to see and do are listed after the day trips.

Day Trips From Montalcino

Trip One: San Quirico, Bagno Vignoni, Castiglione d’Orcia
From Montalcino, take Traversa di Monte towards San Quirico. Follow the signs for Torrenieri. Take SS2 south a couple of kilometers to San Quirico. Park in open spaces alongside town walls on left and enter through the main gate.

Back on the SS2 and follow signs for Bagno Vignoni.
Back to the SS2 south and follow signs for Castiglione d’Orcia and Rocca d’Orcia. From there continue on thru Monte Amiata and Castelnuovo dell’Abate and circle back to Montalcino.

Trip Two: Castelnuovo dell’Abate to Sant’Angelo in Colle
From the traffic circle above Montalcino, take the road to Castelnuovo dell‘ Abate. There is a white road at the entrance to St Antimo. Follow this road to Sant’Angelo in Colle. Do not take the sharp right down to St Antimo unless this is your destination.

You can come back to Montalcino, making this a short route, or you can continue on to pick up Trip Four’s route. If you chose to go back to Montalcino, take the road out of Sant’Angelo in Colle and turn north on the paved road.

Trip Three: Buonconvento and Murlo
From Montalcino head down to the traffic circle at the gas station. Turn left to Buonconvento. Park outside the town and wander its old center.

From Buonconvento, follow the signs to Murlo and Lupompesi (they might also indicate Casciano). From Lupompesi follow the signs to Casciano to see the ruined castle/tower at Crevole.
Either double back or do this trip in reverse after a trip to San Galgano or on the way to San Galgano.

Trip Four: San Galgano and Monte Antico
This trip can be broken up into two or more trips. It is not an efficient drive anywhere, but a grand ramble that has some amazing sights. I have done it both directions, but I think that a long day winding up at La Campanga in Monte Antico or a long day winding up at Bosco della Spina in Lupompesi or even Il Poggiolo, Duccio or Da Mario in Buonconvento both have their charms.

Clockwise: From Montalcino, take the road marked Grosetto. Follow it down past Sant’Angelo in Colle. You can detour to see Castello di Banfi or Camigliano (wonderful village with a great Brunello producer). If going to Camigliano, take the turning off towards Tavernelle and follow the white road. In any case, you wind up going south past San’Angelo Scalo and cross the Orcia river. The road ends at a “T” with the road towards Paganico. Take the right turn towards Paganico. The turn off towards Monte Antico is well signed if you chose to stop there. I do not know if La Campagna is open for lunch (or if they do the Pizzone at lunch).

To go on to San Galgano, continue to the 223, go north for a short bit and follow the signs towards Roccastrada and Monticiano. This is a long, windy route that will take you thru beautiful country. You will be in for a treat in sunflower season on this road (summer). At Monticiano you go northwest; I believe the signs are for Frosini and San Galgano.

You will come to a fairly large crossing with a middle of nowhere gas station just past it. Turn left here for San Galgano and follow the signs. There is the main abbey and then a small church above. There is an okay wine bar by the church.

To get back to Montalcino, take the road back to Monticiano and then take the road that cuts back to the 223. It is indicated S. Lorenzo a Merse. It is a beautiful and very windy drive. There is a turn off to Tocchi worth following. From the 223 go north and follow the signs for Murlo and then back to Buonconvento. You could stop at Murlo for pizza, Lupompesi for Bosco della Spina or Buonconvento for I Poggioli, Duccio (Fiorentina) or Da Mario (very cheap good eats).

Counterclockwise: Head to Buonconvento, then to Murlo across to the SS223. South to the cutoff for Monticiano/San Galgano. From San Galgano, double back to Monticiano and head down thru Roccastrada, Paganico and Monte Antico. You should be able to fill your day and have dinner at La Campagna. The drive from Monte Antico back to Montalcino is about an hour or so.

Trip Five: Monte Oliveto, Sant’Anna and Trequanda
From Montalcino, take Traversa di Monte to SS2 north. Follow the signs to Monte Oliveto Maggiore. The turnoff is in Buonconvento.

After visiting Monte Oliveto, continue on to Trequanda. From Trequanda follow the signs for Montisi and then Castelmuzio (white road route) or Madonino to Castelmuzio (paved all the way). From Castelmuzio, take the road towards Pienza and Sant’Anna is to the right.

An evening stroll in Pienza is a nice addition or continue on to San Quirico and dinner at All’Antico Forno.

Sights Close to Montalcino

This abbey is the most famous sight in the immediate surrounding of Montalcino. It is just outside the village of Castelnuovo dell’Abate, about a 15 minute or so drive from Montalcino. To get there, go to Montalcino. At the traffic circle at the top of Montalcino and follow the sign for St Antimo.

The abbey dates from before the year 1000 but what we see today is more modern. Still it is over 900 years old. It is amazing for its simplicity, setting and lack of ostentation. I find it a powerful place. You can go and hear the services with the Gregorian chanting, but we visited it many a time before ever hearing them. You can hike there from Montalcino and take a bus back from Castelnuovo.

Read more about Sant’Antimo.

Castelnuovo dell’Abate
The town itself is on a little hill and the streets are surprisingly steep. There is a large bar at the entrance to town and Bassomundo is a well know restaurant there of which I have heard mixed things. You are in the midst of some great wineries: Ciacci Piccolomini is the easiest to find and to arrange a visit to. If you go, say hi to Jenna. Their wines are very friendly and approachable for those who are not knowledgeable about Brunello due to the ripeness imparted by their vineyard sites.

Sant’Angelo in Colle
If you are at St Antimo, it is a short drive on a white road to Sant’Angelo in Colle andIl Pozzo, a rustic restaurant that serves superb Fiorentina from Chianina beef. It is worth a detour. Heck, its worth a trip from Siena or even farther! Have the Pinci al Ragu di Cinghiale and Fiorentina and you will be happy. Stuffed and in a stupor but definitely happy.

The village of Sant’Angelo is a delight: simple with a circular layout. It is worth wandering about. It is strikingly lit for nighttime wandering so you can walk before or after dinner. Since some of the streets are pretty steep, so you may not want to challenge gravity after dinner at Il Pozzo. The steep streets offer a treat during the day. You take a side street and all of a sudden you are staring out to a beautiful vista framed in by the walls and narrow path of a street. Great photo opportunities abound!

South of Sant’Angelo in Colle
The road from Montalcino to Sant’Angelo continues on farther south through beautiful vineyards and countryside. This is the home to some pretty large Brunello makers and this district is more of a monoculture than some parts of the area. The grounds ofArgiano and the Castello di Argiano are pretty amazing. Its worth a detour and a short walk. You can only go to the winery by appointment.

Both Banfi and Camigliano are a little ways off the main road. Banfi is down in this area and there are often events held there like the Winter Jazz Fest. Banfi has a restaurant and a museum and incredibly beautiful grounds. I am not a fan of their wines and as such cannot talk about either dining there or tasting there. Camigliano is a wonderful winery making very good wines right now. It is located in the village of the same name and the restaurant there is supposed to be very nice. I think its pretty easy to set up tours or tasting at the winery.

The last town on this bit of road is Sant’Angelo in Scalo. There is reputed to be a good butcher shop there specializing in Chianina beef. If you have an apartment, it’s a good stop for supplies for dinner. You can continue all the way to the end of the road as you cross the Orcia river, you have come to the end of the Brunello zone.

From Sant’Angelo in Scalo, go across the river is the road to Paganico and Mt Amiata. East along this main road is Monte Antico and La Campagna. Monte Antico is a tiny hamlet in the middle of vineyards only accessible by a long and winding road. It offers great views around. I think there is a castle there and you have views of Camigliano and Banfi. This is an out of the way restaurant that has superb (by reputation only, we didn’t have one) Pizzone or large pizzas. If you have two or three NFL linebackers with you (or a teenager or two) you can probably finish one. They are seriously huge and look great. They also make incredible tortelli with potatoes and a topping. I had one a version of the latter with nettles that were very yummy. The wine list is outstanding.

San Galgano
If you go all the way to the Grosetto road (223) and head north a little, you will come to the cutoff for San Galgano. To me, this is a must see, but it is at least an hour or more driving. San Galgano was a major abbey that was abandoned in the 1400s during the wars between Firenze and Siena. The roof was sold for its lead content to make ammunition. Today, what is left is a crumbling shell of the building. It is stark and very moving. There are still functioning portions of the monastery where there is a monastic community. There is an alter and lighting in the abbey so I am sure they have some services there and some events as well.

But I love it for its haunting beauty. It is crumbling and in need of at least stabilization. Since we have been coming there (eight years ago at time of writing) we have seen some of the rose window and some decorative elements disappear from visit to visit. I think it best around sunset. Its very much worth the drive.

After San Galgano itself, you need to hike up the hill (or drive) to the small round church above. The church itself is open to the public but the rest of the buildings are private property. Not only is the view grand, but the church itself is a masterpiece. The dome is banded in black and off white stone and there are Ambrogio Lorenzettifreschi and sinopie (the drawings used to transfer the design to the wall in the making of a fresco) in a small chapel off to the side. Be sure to feed the light box to illuminate them. There is also a wine bar which we did not love especially. The salumi was passable and the wine fairly ordinary. But the setting is nice and the folk friendly.

On the direct road from San Galgano to the 223 you will pass a turn off for Tocchi. I love following the one way road and seeing the medieval buildings in use today. There was a restaurant there, very plain and simple. We passed it by and thought that it either would be incredible or not good at all. I found out later than many considered it incredible. It has closed due to illness or a death in the family. Today it has reopened as Beppi or something like that. It looks larger and not as simple. I know nothing about it but I do want to eat there one time.

Sights Southeast of Montalcino

Taking the Traversa del Monte from Montalcino towards San Quirico leads you on another set of adventures with a totally different geography. Here you don’t have the gently rolling vast seas of grapes as you do to the southwest. The landscape is hillier with more small towns and dramatic vistas.

Torrenieri is a tiny town, reputed to have a good pizzeria. It is a kilometer or two north on the frontage road from where the Traversa meets the SS2. It has a wonderful old church that is seldom open but worth seeing. There is also a winery,Abbadia di Ardegna, with god awful wines, some of the worst I have ever tasted. But it also has a museum of sorts, giving the history of the “torre nero” that gave the town its name as well as a history of peasant farming in the 1930s. Tasting the wine and buying a bottle of the rosso (buying it, mind you, not drinking it!) is a small price to pay to see the tour.

San Quirico d’Orcia
Heading south on the SS2, follow the signs to San Quirico d’Orcia. San Quirico is a lovely town. You drive over the horseshoe shaped old bridge and follow the road and the town will be on your left. Park along the walls and enter through the main gate. There is a garden off the piazza just inside the gate and the main road of the town runs perpendicular to your entry path. Some people like to base in San Quirico rather than Montalcino. It is smaller, quieter and less wine and wine tourist oriented. It has a well regarded hotel, Palazzo dei Capitani. Another advantage is that it is relatively flat and has great access to the SS2.

San Quirico has two churches, one newer with lion porches (basically straight ahead through the gate) and one older one to the far end of the town (through the main gates and to the right). It also has a great restaurant, All’Antico Forno, a very nice bakery and a superb cheese store. The cheese store is beyond the old church and it fabulous. It specializes in family made pecorino. The shop is owned by the youngest son of a sheep raising family. He was tired of shoveling sheep sh*t and he learned to make cheese. It is really quite good, especially the spiced pecorino sott’olio.

Bagno Vignoni
Continuing south of the SS2 from San Quirico, you see a cutoff for Bagno Vignoni (you can also go through the new section of San Quirico and venture up the white road, but I would recommend the simple approach to Bagno Vignoni and take the white road back to San Quirico.

Bagno Vignoni is a gem. There are two spas. The public baths date from Roman times (I think the current version is due to a Medici restoration and a modern reconstruction of the water system). There is a great bar called Il Barino which features live jazz.

By the parking lots, there is a set of ditches that carry the hot water to the edge of the cliff over the Orcia River. These ditches lead to a wonderful historic exhibit. There are two large holding basins and a set of baths there, recently rediscovered. When you have a water source with a large elevation like you do at Bagno Vignoni, you have the chance of having water mills and wealth. The problem at Bagno Vignoni was the rate of the water flow. It was enough to make for really nice hot springs but not enough for the mills. So the holding basins. They were constructed to hold a days worth of water. When full, the exits would be opened and the water volume was enough to run four mills, located down the cliff face. These mills have been excavated and there is loads of signage. The walk down is invigorating and beautiful. The walk up is exhausting, but will enable you to walk off a dinner at Il Pozzo easily. If you do this hike, come early in the day for both the rising morning mists and the lesser heat of an early morning climb back you the cliffs. There are a couple of restaurants in Bagno Vignoni but we have not dined at any of them.

From Bagno Vignoni you can take the white road up to Vignoni and then follow around to Castello Ripa d’Orcia, a wonderful site that is home to a hotel and restaurant of mixed repute. We have just wandered the grounds outside the gates and taken lots of photos. Vignoni is a lovely confection, now used as weekend and vacation homes mostly. The scenery is breathtaking! If you do this drive, you can take the white road back to San Quirico and get a free roller coaster ride. Nothing like a 14 degree drop on a white road!!!

The alternative is to drive back to the SS2 south and follow around in the direction of Monte Amiata thru Castiglione d’Orcia, a drive that is long, winding, castle filled and breathtakingly beautiful. Before hitting Castiglione d’Orcia itself, there is a turnoff forRocca d’Orcia. This is a must do stop, if only for another strenuous exercise opportunity. You will be humbled by all the 90 year old geezers in black sweaters and hats on a hot summer day, smoking cigarette after cigarette who will whiz past you saying “buongiorno” as you are sucking swamp water on your way up. At the top, you will be rewarded with a pretty bland modern sculpture garden, a fortress and some of the best views you will ever see in Tuscany. Its incredible! There is a small entry fee. The rocca itself is well signed and you can learn a little of life in feudal times.

Further along the road is Castiglione d’Orcia, a little town with a castle undergoing what seems to be a fairly large restoration. The town always seems packed with people but we have yet to explore it. From Castiglione d’Orcia you continue towards Monte Amiata and can then turn northwest towards Castelnuovo dell’Abate, St Antimo and Montalcino.

Sights Northwest of Montalcino – Murlo and environs

From Montalcino, take the road down to Buonconvento and then follow the SS2. Some people think of Buonconvento as the cutoff for Montalcino or a railway stop. Whizzing past it, it is easy to ignore. It is set on a plane in a semi-industrial zone. But it has a lovely centro and is worth exploring.

You can park at either end of the Centro but I find the North side easier. Walk to the main gate at that end and you are in the pedestrian Centro which is all of three or four blocks long. There is a Museo dell’Arte Sacre which is definitely worth going to see. In addition, there is a church with some modern touches. But I just love to wander up and back more than anything else.

For dining choices, Da Mario is loads of fun. It is dirt cheap and good. Not great mind you, but good. Most of the diners will be in their usual seats eating their usual orders that no one need to hear them recite. It’s that kind of place. But for a new comer, they will hand you a long menu and then point out the four or five choices from each section that they are offering that day.

Duccio is a Slow Food recommended place, a lot more fussy and formal. Good food, very good Bistecca Fiorentina, nice wine list. I Poggioli in the new section of town is also good and lower priced than Duccio. Very traditional and a bit on the heavy side. They have fish on the menu and as specials which makes for a nice change in Montalcino. The new town of Buonconvento is fairly non descript and lacking in good wine bars etc.

From Buonconvento, there are several routes, all well signed, leading you to Murlo and all routes have their delights. Murlo is a tiny village, very precious with a gorgeous church and spectacular Etruscan museum. Murlo’s claim to fame is that a functional copper casting furnace was found there. Great insight into Etruscan metalwork was gained. The Museo also shows off discoveries like houses and their decorations. The Museo is spread out in two buildings on two floors. It is a fabulous museum and always worth visiting. The signage and information varies from complete with in depth background to almost non existent.

There is a pizzeria/restaurant in the village but I have never eaten there. It comes highly recommended. Murlo is a great stop at dusk as the village is on the hill and surrounded by excellent scenery.

Heading out of Murlo you come first to Vescovado di Murlo, a suburban feeling housing enclave and then the little turnoff that is Lupompesi. Lupompesi is home to Bosco della Spina which is my favorite restaurant in the area. Its food is quite seasonal and offers very modern renditions (in terms of plating and lightness) of classic Southern Tuscan cuisine. It is also truly beautiful as well. Great wine list.

If you follow the road past Lupompesi you will come to the ruined castle of Crevole. It is stunning. Go at night so you see it light up and, well frankly, a little spooky. I would love to see someone make a film there, or maybe stage a production of Luccia di Lammamoor. Its that creepy but beautiful. You cannot get to the castle itself as it is on private property, but there are parking areas and some trails that allow you to get closer.

Sights Northeast of Montalcino

Monte Oliveto Maggiore
From Montalcino, go north on the SS2 until you find the turnoff for Monte Oliveto. It is a few kilometers up the road and well worth a stop. Monte Oliveto is a major abbey still in use today. It is Franciscan today, with a business in old book restoration as well as a restaurant and grounds. They also have rooms for a retreat.

You can spend half a day here easily. Walking the grounds, take in a service with Gregorian chants and then the highlight: the Fresco Cycle by Signorelli and Il Sodoma. The Fresco cycle is on the walls of the cloister. You may run into a tour group or you may be blissfully alone with this masterpiece. I personally am a big fan of Il Sodoma and think him one of the masters of the early Renaissance. His name, translates to the Sodomite and his interest in the male form is quite evident. All the women are basically the same, with nondistinctive figures. The men, however, are all unique and with precise figures (often displayed with hands on hips and bottoms thrust out). Not to be sacrilegious, but his flagellation of Christ presents a quite hunky Christ in a very erotic pose tied to the cross and showing the signs of his scourging. Every muscle and bead of sweat and drop of blood is shown in detail.

Il Sodoma didn’t really understand perspective and its fun to see every mistaken panel with Escher-ian impossibilities of space. Animals show up as often as pretty young boys. Perhaps the best part of the whole is the use of grotesques and the tromp l’oiel panels that frame each scene. Also there is a lot of satire such as the fact that there is a scene where the abbot of the monastery is represented as a devil being thrown in a well. He is shown with donkey’s ears. He made the mistake of disputing a payment to Il Sodoma and was thus immortalized.

Monte Oliveto Travel Guide: More information about the abbey and descriptions of the frescoes.

Sant’Anna in Camprena
From Monte Oliveto, your choices are myriad. I would suggest continuing to Sant’Anna in Camprena. You need to go via Castelmuzio and Montisi. Castelmuzio is a nice stop in and of itself. The old town is elliptical in shape with great views. There is a new town which we did not explore. The church is very nice and, if you can find the caretaker, there is also a little Museo. The bar in town was pretty dreary. There are all sorts of places to sit so that might be the best idea of all. Here you will find another fresco cycle by a much younger Il Sodoma.

We love Trequanda for its simple beauty, its location and its restaurant Conte Matto. Davide is a superb host, the food quite fine and devoted to local and traditional ingredients. The salumi is strongly flavored and made from Cinta Sinese, the local, rare and wonderful pork. The wine list is immense and superb. We dined there on a snowy day and spent three hours watching out the window as the hillside became increasingly white. There is also a fantastic bakery in town.

The church is wonderful for its facade and two freschi inside, one of which is attributed to Il Sodoma (and seems like it could be) and another attributed to him that looks nothing like any of his work. If you dine at Conte Matto, be sure to visit the bakery before or after and pick up some pastries for your next morning’s breakfast. If you are looking for the makings of a picnic, when you turn to drive up to the town itself, there is a huge butcher shop that specializes in the areas finest treats: Cinta Sinese pork products and Chianina Beef. The shop was closed when we went by but I bet you could put together a wonderful picnic at the bakery in town and the prepared and cured meats section of the butcher shop.

Beyond Trequanda is some fine outlet shopping including Liba shirt makers. It’s a great bargain as they make shirts you find at Barneys in NYC for over $100 and even $200 a shirt and you get them at Liba for 45 Euro each. The quality is incredible. Next door is a leather outlet but we did not find anything we could both afford and liked.

There are also signs for roman ruins and churches that you could spend hours following. They will drive you crazy but you will also get some glimpses of pretty amazing stuff. We found a Roman era something or other – bath, sewer, nympheum, who knows! I don’t! But it was amazing, free and deserted!

Also in this neck of the woods is Pienza. We loved strolling it for its renaissance perfection of layout. The Duomo was wrapped iron scaffolding when we visited and a lot of renovation is needed to keep the major attractions from falling off the hill. The main street has about 20 cheese shops most of which are selling the same Coop-made cheeses. I felt like it was a cheese-y Disneyland yet others love it.

This ends my introduction to the surroundings of Montalcino. It is neither balanced or complete. I have nothing about Montepulciano, Montefollonico, San Giovanni d’Asso etc. Some of these are still on my to do list and others just didn’t fit in. It just goes to show that in over 5 week-long visits, staying in Montalcino, we have only begun to explore the surroundings!

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