Best Tuscan scenery
 

Google Val d'Orcia and look at the images.

That is where the movie Gladiator was filmed, around the town of Pienza, which looks out over those rolling vineyards and hay fields. There are small winding roads with cypresses lined up neatly and you see the stacks of hay bales, shaped like cylinders, depending on the time of the year.

You can Google 'Val d'Orcia drives' and someone must have pinpointed paths or drives to take. Of course there are wineries and agriturismi in this area as well where you can stay, though maybe not as convenient as staying in one of the towns near restaurants and markets.

San Gmignano is a medieval town with tall towers. It does not look like Montepulciano or Pieza. The city scapes are all beautiful, just different. S.G. also is surrounded by rolling hills though there isn't really a great vantage point to see the unless you pay and climb one of the towers.

Siena is also beautiful city. Going north to south, it's Florence, S.G., Siena and then the Val d'Orcia with Montalcino, Pienza and Montepulciano. I think Montepulciano in general has the best views from town over the surrounding country side. But it's also great to look around south of Pienza to look northwards with Pienza rising above all these hills.

Thank you so much! This is super helpful. We will stick to Montepulciano and Pienza then. We would be driving back to Florence. Trying to keep our base the same since we have a 4 year old.

The Montepulciano-Pienza-Montalcino route is my favorite views. This area is what you see in most of the postcards of Tuscany. I don't find the drive from Florence to Siena as scenic (the views are not as sweeping and it seems more rustic). If you take that drive, you want the SR222.

**Finally, we will have one additional day in Florence - do you think visiting San Gimignano is worth it?**

I wouldn't imagine you would be keeping your car if staying in Florence as you can't drive in Florence (ZTL). You would have to park outside the ZTL ($$). Of course all these little towns have ZTL too, but not as difficult as Florence or with the number of tickets sent after you return home.

The enoteca Osticcio in Montalcino has sweeping views of the countryside. It's changed hands since I was last there, but the food was good then and you could do tastings of the Brunellos. Too lazy to locate one of my own pics from the enoteca so here is one from the web.

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Finally, we will have one additional day in Florence - do you think visiting San Gimignano is worth it? Or will it be quite similar to Montepulciano and Pienza?

Yes, because in San Gimignano you will eat the best gelato in the world! 😋

We return to the Chianti region because we prefer a green landscape to the yellow of Montepulciano, Pienza , etc.

Vineyards would be nice but I like the rolling hills of mown hay fields which are yellow to golden in color in the summer. Really contrasts well with green trees like the rows of cypresses and the distant green mountains.

Here are some pictures of Val d'Orcia and one near San Gmignano.


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Per what others are mentioning time of year for scenery is critical to the beauty of the area. The Val D’Orcia is very green in spring and somewhat green in fall, including areas not under irrigation. About the beginning of June the heat intensifies and rain stops drying out everything that is not irrigated, that’s were the brown tan landscapes come from. I prefer the green and would only visit Val D’Orcia in spring or fall, never summer. For other reasons too I would not travel to Italy in summer.
Another area to visit for the landscape beauty is south of Montepulciano around the famous farm and gardens of La Foce, more pronounced rolling hills dotted with cypress trees, vineyards and farms. There’s a famous picture of a winding road going up a hill lined with the cypress trees which is near La Foce.

North of Pienza in the middle of Val D’Orcia is an area known as the Crete sensi. Rolling , smaller hills where you can see for greater distances. The soil is different a mix of sand and clay and there are many places to view dramatic displays of erosion as the soils tend to collapse over time. Very interesting abbey is located in this area, Monte Olivetto D Maggiore, still functioning abbey with frescoes, monks chanting daily, good views of area and more.

The town of Montechiello situated between Pienza and Montepulciano is a very small hill town up on top of a higher hill. It has a couple restaurants on the towns edge with great views of valley and Pienza in the distance.

Montalcino is very close and I would suggest a visit for tastings of the brunellos if your a wine drinker. There’s a very small wine shop/tasting room located inside the fortress, fortezza, of Montalcino. From inside the wine shop you can access the stairs to walk the ramparts of the fortress with great views over Montalcino and Val D’Orcia valley. The staff at the enotecca in the fortress are very knowledgable about the wines.
Endorsing what the bourbon lover mentioned about Osteria Osticcio, great place, great views of Montalcino and the valley ,
One of my favorite places in Tuscany to eat, drink and enjoy the view. Haven’t been since new ownership took over.
One year I arrived in March after a 4-5 inch snowfall. Sitting at the windows of the Osteria enjoying the views of my first snowfall in Italy was fantastic.

However beautiful this area is I enjoy the vineyards and tree topped hills of Chianti more then the valley area. If you have not visited Chianti I would suggest viewing some photos of the Chianti area to see if you would also enjoy seeing the beauty of this area.