Home » Europe » Tuscany Scenic Drive: Pisa, Volterra, Siena to Pienza

Tuscany Scenic Drive: Pisa, Volterra, Siena to Pienza

Tuscany is full of scenic roads and it’s hard to choose which one to take. We took a flight to Pisa, rented the cutest little Fiat and hit the road. And I think we found the best places Tuscany, Italy has to offer. You can follow our Tuscany scenic drive and absorb the beauty – and then start planning your own trip!

This is a view from Volterra, one of the prettiest Tuscan hilltop towns we visited. And there were so many views like this on our itinerary through the Italian countryside.

Tuscany scenic drive view from Volterra

Tuscany scenic drive: Volterra

Below you can see on the map which part of Tuscany we were exploring. We started in Pisa, first north and then south, and ended up at Pienza. Driving this route took us a many days since we were stopped a lot, stayed nights in Tuscan villages and followed small country roads.

Tuscany Scenic Drive Map


This is a map of Tuscany, Italy and you can see our itinerary on the map, from Pisa airport to Lucca and on to Volterra and San Gimignano.

From San Gimignano our road trip continued to Siena and Val d’Orcia where the biggest town is Pienza.

So we started in Pisa:


Tuscany scenic drive Pisa townhouse

Tuscany scenic drive: Pisa

We landed in Pisa just before midnight, took our cute little Fiat and headed to the city. That was a short drive, the airport is almost in the city. Our hotel was in a lively quarter, lots of students were having fun in the streets and the cafes were full on people. We were in Italy!

This is not our hotel, it’s one of the typical town houses Pisa is full of. Italian houses!

 Tuscany Scenic Drive Trattoria

Typical trattoria in Pisa, Italy

Even all the trattorias and piazzas where farmers were selling their products looked so Italian.

Below you can see the great choice of local farming products on the local marketplace. And so many zucchini flowers, they that are my favorite!

Tuscany scenic drive Pisa vegetable market

Pisa vegetable market

Tuscany Scenic Drive zucchini flowers

Zucchini flowers for sale

Pisa vegetable market

More Tuscan vegetables

Pisa is a historic city. It was a dominant city in the Western Mediterranean in the 12th century. Many of the old houses date back to that time.

Tuscany scenic drive Pisa side street

Pisa, Italy

This is the river Arno that flows through the city. The Pisa area doesn’t really look like what you expect Tuscany look like. It is flatland, the Arno valley. Pisa is an industrial city with 90 000 recidents and a university.

Tuscany scenic drive Pisa

River Arno

A short walk north of the city are the Campo dei Miracoli and the Torre Pendente, the Leaning Tower of Pisa.


Tuscany scenic drive Pisa street view

Towards Campo dei Miracoli, Pisa

The Leaning Tower of Pisa

Tuscany Scenic Drive Torre Pendiente

The leaning tower of Pisa

As you know the Leaning Tower is the most famous sight of Pisa. Why is it leaning like that?

The tower was built in 12th Century on a soft land and as soon as when the third storey was made the tower started to collapse. Yet they decided to build the tower eight storeys high which took almost 200 years. The next stages were planned differently so they tilted in the opposite direction.


Tuscany Scenic Drive Pisa Duomo

Campo dei Miracoli, a UNESCO site

The tower is not the only thing that’s leaning. All the other buildings are leaning too. You can see the leaning Duomo and the leaning Battistero tower in the picture.

Campo dei Miracoli

The Campo dei Miracoli area has many more great buildings. These photos show the Campo Santo cemetery that is carefully being restored so it will stand here for another thousand years or more.

Campo Santo

A historic arcade

We got our tickets to the Leaning Tower. There was a waiting time of about an hour or two but you could stroll around and look in the other buildings during that time. This is a view down from the tower.

Pisa street from Leaning Tower

View from the Leaning tower of Pisa

After you’ve seen the other buildings the Leaning Tower of Pisa is not leaning that much any more. In fact it isn’t leaning as much it could.


Tuscany Scenic Drive Pisa leaning tower

The tower

In 1989 the Pisa Tower was rapidly closed to the public since it was already leaning too much. It almost collapsing.

The tower was straightened by 40 cm and steel was added to stabilize it. This all took two decades and today the tower is open to public again but they limit the number of visitors that can access the tower at the same time.


Tuscany scenic drive Pisa statue

Roumulus and Remus

In front of the ticket office is a statue of Romulus and Remus suckling on the wolf. This is so Italian!

The Campo dei Miracoli area has been given the status of a UNESCO World Heritage Site.


Tuscany scenic drive Lucca marketplace

Tuscany scenic drive: stopping at Lucca

Before heading south we took a side trip to Lucca that is a historic town 20 km north of Pisa. Lucca is surrounded by a red brick defence wall that you can walk on. You can walk all the way around the city.

Lucca is a Roman city and its marketplace Piazza Anfiteatro looks like an amphiteatre. It was a Roman theatre but the seats were little by little replaced by townhouses.

Tuscany scenic drive Lucca house

Lucca, Tuscany

There are lots of narrow lanes where you can walk, historic palazzi and museums – and pavement cafes where on a hot day nothing tastes better than an Italian tomato bruschetta.


From Lucca it is a pretty long drive to the first hilltop town Volterra south of Pisa. Instead of busy highways we took small country roads.


Tuscany scenic drive road trip

Driving in Tuscany: our Fiat 500


Tuscany scenic drive Volterra landscape

View from Volterra

Volterra is so pretty. It’s an old Etruscan city high on a hilltop. The views are great in all directions.

Our original plan was to make a bike trip to Tuscan hilltop cities. Later we changed this plan as we noticed how high the hills were, climbing the hills on a bike would mean too much physical effort.



Volterra has narrow lanes and alleys that were built at a time when no cars existed. But you can park your car outside the city walls and walk.

Tuscany scenic drive Volterra twilight

Volterra Twilight scene

This is The Palazzo dei Priori, the Volterra Twilight scene.

Volterra is so pretty that you could stay a few nights but we had booked a room in the next hilltop town San Gimignano.

San Gimignano

Tuscany Scenic Drive San Gimignano hill view

Best places of Tuscany: San Gimignano

So the next stop was San Gimignano. It is the best-preserved medieval city in Tuscany so we booked a room there at a small bed and breakfast on the main street Via San Giovanni.

That was a big family apartment and we felt like being their guests even if understanding each other at times caused some problems. We had a balcony to the inner court where we could see and hear the neighbors spend time and work in their small gardens.

San Gimignano looks like nothing has changed since the middle ages. Like elsewhere in Italy the whole town is a walking area and you leave your car outside the town gate.

But there is one thing that’s not just like it used to be. It’s the towers. San Gimignano used to have 76 towers. They were built to be private fortresses of wealthy families. Time has destroyed most of these towers and only 14 towers remain.

San Gimignano is an imposing view even with these 14 towers. They look like medieval skyscrapers. San Gimignano is a medieval Italian Manhattan.


Tuscany Scenic Drive San Gimignano street view

San Gimignano square

Piazza del Duomo has a palace with the oldest tower and Piazza della Cisterna has a 13th century well and another medieval palace.

Tuscany Scenic Drive Fiat

Another Fiat cinquecento

We found a small car on the narrow lanes… This Fiat was an older model and still smaller than ours. Old Fiats like this are still very common in Italy.

Toscana Scenic Drive San Gimignano hill view

Tuscan countryside from San Gimignano

Vineyard Walk

Tuscany Scenic Drive San Gimignano

Walking in Tuscany

San Gimignano is a good destination for hikers.

There are many marked walking tracks in the countryside around the city, or in fact they are not so well marked.

Tuscany Scenic Drive view

Italian countyside

We got a walking map from the tourist office and took a 15 km loop trail to walk the countryside and vineyards.


Tuscany Scenic Tour vineyards

Tuscan vineyard

And we saw just amazing countryside! Small farms, vineyards and wineries. We mostly walked along small country roads and partly on paths. But somewhere we got lost, and lost again despite the map. There must have been a missing road sign.

So we walked and walked and it was hot. Good we had brought water bottles.


Back in San Gimignano we counted we had walked more than a half marathon, 25 km instead of 15. But it was a beautiful walk, and very scenic almost all the way – with the exception of the massive industrial area where we walked about three to four km.


Tuscany Scenic Drive olive trees

Olive garden

Then it was time to leave San Gimignano. We followed the Val d’Elsa valley to Poggibonsi and on to Siena in the south. Half way to Siena was a small village, Monteriggioni.


Tuscany village

The Tuscan hilltop village of Monterriggioni

Monteriggioni is a small hilltop town and we stopped there, just off the road to Siena.

Like San Gimignano Monteriggioni has thick walls and 14 towers from the 13th century. The towers have been guarding the area.


This is another pretty town! Monteriggioni has many craft shops and cafes. It is a popular stop for tourist groups. The small sleepy village wakes up when tour groups arrive.


Tuscany view

Crete Senesi, Tuscany road trip

On the way to Siena there’s a lot of green forest and partly open landscape with rolling hills.


Siena Piazza del Campo

The Palio of Siena

The next hilltop town is the 14th century Siena that is much bigger than the other hilltop towns we have been to.

Piazza del Campo

The absolute center of Siena is the shell-shaped Piazza del Campo that’s straight on one side and curved on the others.

What is special Il Campo is divided into nine sectors because a council of nine has governed Siena in the middle ages. In Siena the principle is that all streets lead to Il Campo.

Elegant Palazzi surround the piazza and a fountain Fonte Gaia is right in the middle. There is a good choice of pavement cafes on the curved side of the Campo.


The huge building that looks like a castle is the Palazzo Pubblico. It’s a Gothic town hall with a bell tower. You can climb 500 steps up to the bell tower Torre del Mangia for a superb view of the square, the whole Siena and Tuscany.

The piazza is where the famous Sienese Palio is held each year in the summer.  It’s a horse race where the jockeys dress in colored medieval clothes.

Siena Duomo

Siena Duomo

Sieno Du0mo

Another famous sight in Siena is the striped marble cathedral Siena Duomo that looks a little bit like a mixture of building styles.

The black and white marble comes from outside the city and the cathedral is black and white on the inside as well. Even all the pillars inside are all black and white striped like liquorice. Go inside so you see it.


Siena Duomo

Beautiful places in Tuscany: Siena

After Siena it’s on the road again, stopping now and then if you like the scenery. We stopped quite a lot before Monticchiello that was the next town we visited.


Driving in Tuscany

Driving in Tuscany

This is what the scenery in the Montichiello area is like – looks like Tuscany in post cards.

Tuscany hills

Rolling hills of Tuscany, Italy


Monticchiello cafe

Postcard-pretty Monticchiello

Monticchiello is the smallest hilltop town of those we visited. But one of the prettiest, very quiet and peaceful and no tourists at all around.

There was a cafe with great views and good expresso. The cafe was in the city wall and it was like a small castle.

Monticchiello view

More Monticchiello views

Some more views of Montichiello before we pass through the town gate and get to the final destination of our Tuscany scenic drive.

Monticchiello town gate

Val d’Orcia, one of the most beautiful places in Tuscany

Pienza is just a short way from Montichiello if you take the direct route along small unpaved country roads. This is real Tuscan countryside!


Tuscany scenic drive vineyards

Val d’Orcia vineyards


Tuscany scenic drive Pienza

Visiting Pienza

This is Pienza. And Pienza doesn’t make an exception, it’s on a hill like all other towns.

Pienza was built in Renaissance style by a Pope who was from here. Of course not everything is Renaissance, but everything is pretty. There are beautiful alleys with nice old street names, pretty squares and lots of flowers everywhere.

And the Tuscan scenery…

Tuscany scenic drive Pienza

Fantastic Pienza scenery


Pienza has good restaurants and accommodation since lots of travelers want to visit and maybe stay for a while. Both Italian and foreign people like Pienza.


Pienza cat

A Pienza cat

Driving around in Tuscany

We stayed here for several days, in an agriturismo that I will tell about in another post about our agriturismo holiday in Tuscany. We visited many local sights, walked and biked and saw more hilltop towns, one of which is Montepulciano.

Below you can see us driving around in the beautiful Pienza landscape.


Tuscany scenic drive

Tuscany scenic drive: whereto next?

From Pienza we took the fastest road back to Pisa from where we took a flight back home. But if you have more time than us you can continue your own Tuscany scenic drive to east. That’s a beautiful area too have I heard.


You might also be interested in these articles:

My other blog posts on Tuscany:

Cinque Terre with its five fishing villages is a beautiful coastal area north of Tuscany. This post presents you Cinque Terre:

Rome is just 1,5 hours by train from Florence. Spend a day or two in Rome and see Rome’s top sights:

What to see in North Italy:

Share this if you liked:


  1. Dottie & Joel Savilonis

    I enjoyed your detail on driving in Italy. We are planning on the same type adventure in early Spring 2019. It will be our first visit to this country. Umbria and Tuscany is the plan, ending in Rome for 10 days.
    Would you recommend any particular airport, or start in the bigger city first?

    • Hi Dottie and Joel, I think you could buy return flights to Rome which might be cheaper than booking one-way flights. Then take a rapid train to Florence, 1,5 hrs and after exploring Florence rent a car and drive around. That’s what I’ll be doing next week. You can follow me on social media for travel photos and tips, I’ll be posting every day.

Leave a Reply

Your email address will not be published. Required fields are marked *


This site uses Akismet to reduce spam. Learn how your comment data is processed.

Do NOT follow this link or you will be banned from the site!