TRAVELLING TO PIENZA AND MONTEPULCIANO - Where is the Real Tuscan Landscape?

The typical Tuscan landscape around Siena

TV, Cinema, Magazines, Books always identify Tuscany with soft blonde hills, cypresses at the horizon and isolated houses and villages dotting the fields.

These landscapes are quintessentially Tuscan, but not in every part of Tuscany you will be able to see these landscapes.

Tuscany is a big region extending from the sea on the West to the Apennines in the East.

So if you want to see the most iconic landscapes in Tuscany you need to know where to go!

This is what this post is about, answering the question: Where is the real Tuscan landscape?

Some tips for you to discover the "Real Tuscan Landscape":

Fly to Pisa or Florence where the two main airports in Tuscany are situated.

Although Pisa and Florence areas are also very beautiful the landscape you see in the photos in this post doesn't belong to those areas.

My advise, if you have time, is to allow some time to visit Pisa (read here about Pisa) and Florence (read here about Florence) and then move to the Real Tuscan Landscape.

From Pisa or Florence travel to Siena, both towns are well connected by bus or train.

Siena is certainly worth a visit and it is a perfect base and a wonderful city to discover (read here more about Siena).

Siena is the starting point of the "Real Tuscan Landscape".

After having visited Siena move South towards Montalcino driving or walking or cycling along the Via Cassia.

The Via Cassia is an old Roman road and now a fast road towards the South and eventually Rome.

This section of the Cassia is not too busy (for the Italian standard) and connects many little and picturesque villages along its way and the famous historic towns I listed below.

As an alternative to driving, having much more time at your disposal, the Via Cassia is a good road to walk and cycle, being enough villages to stop along the way for rest and food and certainly lot to see.

Along the way it is certainly worth to stop and visit Montalcino famous for its red wine production and for a beautiful Medioeval town.

A beautiful medieval town with lots of small cobbled streets that will certainly make a very good base for your explorations in the area. Nice restaurants and a lot of small bars will offer you the best attractions in the evening.


From Montalcino keep going towards Pienza, an absolute masterpiece of Renaissance architecture with an amazing history to tell.

Pienza is a unique place to visit (and it is probably worth a post in itself). What makes Pienza special is that this Renaissance towns hasn't been built through the time but it represents the realization of  the project of just one mind who planned the whole town under the Reinassance canons. It is perfect: it is the masterpiece of Renaissance City Planning.

From Wikipedia: "Pienza was rebuilt from a village called Corsignano, which was the birthplace (1405) of Aeneas Silvius Piccolomini (Italian: Enea Silvio Piccolomini), a Renaissance humanist born into an exiled Sienese family, who later became Pope Pius II. Once he became Pope, Piccolomini had the entire village rebuilt as an ideal Renaissance town. Intended as a retreat from Rome, it represents the first application of humanist urban planning concepts, creating an impetus for planning that was adopted in other Italian towns and cities and eventually spread to other European centers.

The rebuilding was done by Florentine architect Bernardo Gambarelli (known as Bernardo Rossellino) who may have worked with the humanist and architect Leon Battista Alberti, though there are no documents to prove it for sure. Alberti was in the employ of the Papal Curia at the time and served as an advisor to Pius. Construction started about 1459. Pope Pius II consecrated the Duomo on August 29, 1462, during his long summer visit. He included a detailed description of the structures in his Commentaries, written during the last two years of his life".

Pienza - arriving cycling along the Cassia Way  

From Pienza you are not too further away to Montepulciano, another Tuscan town famous for its red wine and for its history that certainly deserve a stop and a visit.

You can drive this section of the Via Cassia in one day, if you just want to admire these wonderful panoramas without stopping in any of the town mentioned.

...finally the main square of Montepulciano enjoying a glass of local red wine.

more of Montepulciano square

If you are going to drive along the Via Cassia and stop to visit the towns as suggested consider at least a week including the visit to Siena.

If you are cycling or walking, it is much more difficult to estimate how much time as you need as it depends a lot for your grade of fitness, but I will suggest at least 15 days for the full tour cycling and three weeks trekking.

Piazza del Campo - Siena

Read our post about Siena to read useful info about how to get to Siena.

Read our page Visit Italy for more info and posts about Italy.