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Southern Tuscany Drive

Stu Dudley

One Day Drive through the Val d'Orcia in southern Tuscany

My wife and I feel the Val d'Orcia (around Pienza) in Southern Tuscany has some of the loveliest countryside in Europe. Here is a one day driving itinerary through this area, with stops at various villages and sites. This can be done as a day trip from Siena, with several points along the way where you can head back to Siena early if you like. At most, you will only be about 1 hours away from Siena anywhere on this route. If you have more time to spend in this vicinity, by all means drive down some of the dirt roads and even take some walks. The countryside south of Pienza is a lovely area to do this in.

The best time of day to see this area is in the early morning or late afternoon when the sun is lower in the sky. Many of the views are south of the road, so the sun may be in your face at times during mid day and the sites might not look as striking as they do when the sun is lower. Also, when the shadows are long, the cypress trees and umbrella pines look more spectacular as they are "dancing up the hill" (my wife's term). The farm houses sprinkled throughout the landscape take on a special look in the early morning and at sunset. Budget at least two rolls of film for this area. The Val d'Orcia can get some morning fog. If so, spend the morning in a village and start your drive when the fog lifts.

In my opinion, the countryside is the "star" in this section of Tuscany. You "must see" Pienza and there are other interesting villages too, but don't short change the drive through the countryside. If you are behind schedule, skip some villages - not the countryside. You might think that this itinerary seems out of order in places and I'm often taking you down roads that you have already driven down. Sometimes, I'm considering the position of the sun when you drive on a road, and other times I'm just trying to extend the time in the countryside.

You will need the Touring Club Italiano map of Tuscany to follow this route. Also, obtain the Michelin Green Guide to Tuscany. If anyone wants to take walks in this area, get the Carta Turistica e Stradale - Val di Chiana, Val d'Orcia map. They might have it at the bookstore in Pienza.

Start the drive at Montepulciano

The best place to start this drive is from Montepulciano. For those who have no trouble navigating small roads through the countryside, leave Siena by the N438 to Sinalunga, and then follow your map to Montepulciano.

For those who don't have confidence in navigating through the maze of smaller roads, leave Siena by the N2. Just past the turnoff to Montalcino, look for a beautiful grove of cypress trees to your right. At San Quirico, take the N146 east to Montepulciano. This is an easy drive.

If you leave Siena by 7:00 you should get to Montepulciano by 8:30 or earlier.

Do not visit Montepulciano at this time, unless it is foggy, in which case you should wait until the fog lifts before proceeding on this drive. Take the N146 west to Pienza. The sun will be at your back. When you pass the large white domed church of San Biagio (on your right/north) just after leaving Montepulciano, look back towards Montepulciano and you will be rewarded with a spectacular site - the Church of San Biagio in the foreground with Montepulciano cascading down the hillside behind it. This is one of the most photographed sites in Tuscany. Before I retired, I had a giant poster of this view in my office - reminding me why I wanted to retire and spend more time traveling. Don't take a picture just yet - you will be back over this route later in the day and the sun will be in a better position to shine on the church and the perched village behind it.


Continue on the N146 to Pienza. This road has some wonderful scenery. You should get to Pienza by 9:00 or 9:30.

As you approach the "old" part of Pienza, there will be parking areas to your left - next to the town. Look for these lots on your Michelin Green Guide. If these parking spots are filled, turn around the car and park in a dirt lot just east of the old town and north of the N146. This lot is down a road, so you might have to hunt a little. During tourist season, you have to pay to park in this lot. You can also park south of Pienza below the village, but you will have a slight climb uphill to the center of town (look for the road to this area in the Green Guide).

Explore Pienza by entering through the Porta al Murello, at the west end of Pienza. Just as you enter Pienza, there is a nice pottery/gift shop on your left (in the large square) which has had a significant impact on my wallet. You can obtain a self guided 1 hour tour of the town (in English) by renting a head set from the tourist office (closed at lunch time). If you want to have a picnic lunch at Sant' Antimo abbey, pick up some lunch provisions while in Pienza. There is a pizza shop just outside of the Porta al Murello (next to the book store/news stand) where you can pick up a slice of pizza. There is a walking path next to the town walls on the south side of Pienza - don't miss this. It's a great place to just sit in the sun and admire the views (see the Green Michelin Guide). Plan on spending 1 1/2 hrs in Pienza.

Pienza to Montalcino

Leave Pienza on the N146 toward San Quirico. This is another stretch of road with fantastic views. Just 2K from San Quirico, there is a splendid view to the south of a very small church and another building with cypress trees and umbrella pines surrounding these buildings. This site is on the crest of a hill. If you have been in Tuscany for any length of time, you will have seen this view on many postcards and calendars. As you approach San Quirico, drive into the parking lot behind the Taverna del Barbarossa restaurant (which is associated with the Casanova hotel). The parking lot is at the south end of the complex. Park the car, get out and you will see another of the most photographed sites in Tuscany. In fact, the very first picture that appears in my Michelin Green Guide to Tuscany, is a photograph of this scene - a farm house sitting on top of a hill, surrounded by cypress trees. A "coffee table" book I have, has photographs of this site at different times of the year - it's quite remarkable. This site is even on the cover of my coffee table book. I also have a poster (yes, it was hanging in my office too).

You should get to San Quirico by 11:00. Don't visit San Quirico now - do so later in the itinerary if you have time (it's worth a visit).

Follow the signs at San Quirico and get on the N2 toward Siena (north). Just after you leave San Quirico on the N2, you will be on a bridge. If you look back, there is a nice view of the village of San Quirico from the bridge. Unfortunately, I have never been brave enough to get out of the car and take a picture from this bridge. Further along the N2 there is a pretty grove of cypress trees on your left (west). This grove can be seen better traveling south, however. On your right, you will see several cypress trees and umbrella pines dotting the ridge of a hill. You might recognize this site from postcards and calendars you have seen. Turn off the N2 and go to Montalcino.

Montalcino and Sant' Antimo

As you approach Montalcino, you will get some good views of this perched village. The road will turn a few times and will take you south of the old village and then west of the village, where you can park (hug the village to your right at all times). There is a rather large car park near the old fortress (Rocca). Note - as you turn right from the south side of the village to the west side, look for the street sign to Sant' Antimo Abbey, where you will go next.

Visit Montalcino. You should get there by 11:30. Many shops will close by 1:00. You can visit the fortress, but I found it only OK. Budget about 1 hour or less in Montalcino. It has some nice outdoor lunch spots if you want a sit down lunch but I'm pushing the picnic at Sant' Antimo which is next on the tour.

Follow the signs (and your map) to Sant' Antimo Abbey. The Abbey is quite lovely, but what I like best about it, is the setting - we've used up a lot of film there. It's located in a valley with hills all around, cypress trees dancing up the sides of these hills, and a lawn in front of the Abbey (where you can picnic). It's also a good place for a little snooze in the sun.

Sant' Antimo to Castiglione d'Orcia to Pienza

Continue on your drive through the countryside. You should leave Sant' Antimo about 2:00 or earlier. Take the road south-east of the abbey, toward Monte Amiata on your Touring Club map. Pass through Monte Amiata, and at Ost. Ansidonia, turn left (north-east) to Castiglione d' Orcia. This is pretty countryside. Pass through Castiglione and get on the N2 and head north toward San Quirico. You should get to San Quirico about 2:30 - 3:00.

Continue past San Quirico toward Siena. Get off the N2 at Torrenieri. There is a road that runs from Torrenieri to San Quirico, just east of the N2. Find it on the Touring Club map. You want to head south from Torrenieri to the "phantom" village of Bellaria on the map (there really isn't any village there). When driving through Torrenieri just after leaving the N2, you will turn right in front of a church and you will immediately cross a railroad track. When you get to Bellaria, turn left (east) to Cosona (it's marked at the turn). You will be on a dirt road. It is one of our favorite drives in this area. As soon as you get on this dirt road, look west (right) and you will see more umbrella pines and cypress trees dotting the top of a ridge. I think these are the same trees you saw from the N2 on your drive to Montalcino. Continue and go slowly on this dirt road. Lots if pretty sites here. This dirt road will kind of dead-end onto another dirt road (see it on your map). Turn right toward Pienza and continue on to Pienza. When you get to the N146, turn west (right) toward San Quirico. You should be at this point around 3:30 or earlier.

Possible Return to Siena

Look at your watch and consider what time it is. You are about 1 hour from Siena, so if you got a late start this morning, dawdled longer in the villages, snoozed at Sant'Antimo, or are pooped out now, then head back. You could instead go to Montepulciano (20 mins) take the picture I mentioned earlier and visit the village (1 hr) and head back from there (1 hr); or you could go to San Quirico (10 mins) and visit (45 mins) and head to Siena from there (1 hr) There will be some more places later in this itinerary where you can "cut out" early if you like.

Continuing the Drive, to La Foce, Monticchiello, Montepulciano

For those hearty souls, let's continue the itinerary:

About half way to San Quirico, there is a dirt road that heads south of N146 - find it on the map (it's the only one on the map between Pienza and San Quirico). Turn south on this road. We have often driven down this road, parked the car, and taken off on a hike. You will pass a nice grove of cypress trees. Continue on this road until it connects with the N2.

Continue south on the N2, and after about 2K, head east on the paved road (marked yellow on the touring club map) toward Chianciano and Pienza (well marked). This road passes through another "phantom" town called Spedaletto - find it on the map to make sure you turn at the right place off the N2. This road goes trough the heart of the Val d'Orcia and is quite picturesque. Continue on this road toward Chianciano Terme. You will have a nice view of Pienza perched on top of a ridge, off in the distance to the left (north). There is an "interchange" on this road - pay attention and keep heading to Chianciano Terme.

Around La Foce, you will see a lovely double set of cypress trees to the north, dancing (again) up the hill (another much photographed site). Drive further on this road toward Chianciano Terme, but don't go as far as Chianciano Terme. Actually, I'm not exactly sure where this nice set of cypress trees is located near La Foce, so go on this road until you see this double set of cypress trees, and the road becomes less scenic. Turn the car around and retrace your route. At La Foce, head north to Monticchiello. This is a very cute village - it's where my father-in-law says he wants to live. Park the car in the lot outside this village near the refreshment stand (do you need any) and wander around. It's a 30 min wander. After visiting Monticchiello, head north-east on the road to Montepulciano and connect with the N146 again.

Now you get a better shot at the remarkable view of the San Biagio Church in the foreground, with Montepulciano in the background (you may have to drive a little west on the N146 to get the view). Hopefully you are at this spot about 4:30 - 5:00 or so. Without any stops, you are less than 1 1/2 hrs from Siena. It's a good time to check your watch again to see if you need to head home.


Visit Montpulciano, if you like (1 hr visit). It's a somewhat steep walk through town, however, but the village is very pretty. You can taste some excellent wine at the Avignonesi estate (you will see it). If you need a snack, find a place where you can get pizza by the slice and have a truffle (tartufi) pizza (only in Italy!!!).

Montepulciano to San Quirico

Drive along the N146 toward Pienza and San Quirico again (30 min drive). The sun will be in your face, but now the little church with the cypress trees around it will look quite different, as will other sites you took pictures of when you drove this route in the morning.

San Quirico

If time allows, visit San Quirico (it's 45 mins to Siena from SQ). San Quirico is kind of a poor man's Pienza - but they like it that way. It's a town where people really live. In fact, I've told friends that San Quirico is the type of town we wish our small towns in the US would be like - kind of a River City, Iowa. Everyone knows everyone else, people are out strolling, there are stores where locals shop for their everyday stuff, etc. Families congregate at the Bar Centrale in the evening, where the men play cards in one room, the younger children are in the video room, and the older children are outside playing soccer in the town square or just hanging out. If you visit San Quirico, have a coffee latte at the Bar Centrale and "people watch". SQ is a 30-45 min visit. Some stores may be closed Wednesday afternoon.

Back to Siena

Take the N2 back to Siena.


War in the Val d'Orcia by Iris Origo. This is a woman's diary of happenings in this area during WWII. Non-political, it is an elegantly simple chronicle of daily life at La Foce, a manor in Tuscan no-man's land bracketed by foreign invasion and civil war. The Marchesa Origo's faithful record is one of those rare and precious accounts that give the truth of history with the art of a gifted writer, that bear witness nobly to ignoble times. The preceding was lifted from the back cover of the book. While we were there in '02, they were celebrating the 100th anniversary of her birth.

Slow Travel - Driving - Road Maps: Suggested road maps

Slow Travel - Tuscany Travel Notes - Cypress Roads: Walking through the cypresses near Pienza, other suggested driving routes

Slow Travel - Tuscany Travel Notes - Sant Antimo: Schedule of chanting

© Stu Dudley, 2003

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