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Tuscany Scenic Drive: Pisa, Volterra, Siena to Pienza

Tuscany is so packed with scenic, winding roads that it’s hard to choose which one to take. We searched for a long while and then planned our Tuscany scenic drive, starting from Pisa and ending at Pienza.

The next step was to take flights to Pisa, rent a cute little Fiat – and hit the road.

I really think we found the best places the region has to offer.

I will now take you on a journey across Tuscan hills and valleys. You will breath fresh Tuscan pre-summer air  – and hopefully get ideas for your own dream trip to this lovely region.

Tuscany scenic drive view from Volterra

View from Volterra, one of the hilltop villages along our Tuscany scenic drive

This is Volterra, one of the pretty hilltop towns we went to. But that’s not the only one. There were countless views like this. If you take this trip, reserve time, don’t make your time schedule too tight. You will want to stop.

Map of Our Tuscany Scenic Drive

The map shows which parts of Tuscany we went to:


Map of Tuscany and our driving itinerary through its prettiest parts

As we landed in Pisa, we started there. If your flight is to Florence, you should see the city first and then rent a car and take the country road. Here’s what to see Florence: Florence in One Day: Explore the UNESCO Listed City

First we went to see Pisa and then Lucca, after which it was all the time southward, up to Pienza. On the way the first places to stop at are the hilltop towns Volterra and San Gimignano.

From San Gimignano, the road led to Siena and through the rolling hills of Crete Senesi to the UNESCO listed valley of Val d’Orcia, the valley where Pienza is.

We proceeded very slowly as we stopped all the time to hike along meadows, vineyards and country roads. The nights we stayed in the prettiest hilltop villages, dining where village locals dined. As it was May, there were not many tourists around yet.

Before taking the winding roads, we will have to have stay for a while in Pisa:

Walk in the Old Town of Pisa

Tuscany scenic drive, a typical Pisa townhouse

Tuscany scenic drive, Pisa: yellow walls and green shutters

As we landed in Pisa late in the evening, just before midnight, we only took our cute little Fiat and stayed the night in the city. As Pisa airport is almost in the city, that was a short drive only.

Our hotel was by the riverside where crowds of students were having fun outdoors in the warm evening. All cafes were full on people. We had landed in Italy!

In the morning we went to see what Pisa looks like.

Tuscany Scenic Drive, a Trattoria

A very typical trattoria of Pisa, Italy

In the morning all trattorias and piazzas were already packed with locals and farmers were selling their products. To me, this all was something so Italian!

Below you can see the selection of local farming products on the marketplace. So many zucchini flowers, my favorites!

Tuscany scenic drive Pisa vegetable market

Pisa’s fruit and vegetable market

Tuscany Scenic Drive, zucchini flowers

Delicious zucchini flowers for sale

Pisa vegetable market

.. and even more Tuscan vegetables, directly from the farmers

Everybody knows that Pisa has a leaning tower, but did you know that Pisa is a historic city? Already in the 12th century Pisa was one of the major cities of the Western Mediterranean and many of the old houses in the city are from that time.

Tuscany scenic drive Pisa side street

A typical street of Pisa, Italy

This is the river Arno that flows through the city. It comes from Florence and flows on to the Mediterranean. On both sides of the river is the Arno Valley that is an extremely flat area. That makes the Pisa area look different what you expect Tuscany be like.

The valley is highly industrialized, and Pisa, too, is basically an industrial city with 90 000 residents and a big university.

Tuscany scenic drive Pisa

River Arno

Then: a short walk north from the old town are the Campo dei Miracoli and the Torre Pendente, the Leaning Tower of Pisa:

Tuscany scenic drive Pisa street view

Walking towards Campo dei Miracoli and the Leaning Tower of Pisa

Climbing the Leaning Tower of Pisa

Tuscany Scenic Drive, Torre Pendiente

Torre Pendente, the leaning tower of Pisa

As you know the Leaning Tower is what tourists come for to Pisa. But why does it lean like that?

As they built the tower in 12th Century, they built it on a soft land. Consequently, as soon as the third storey was completed, the tower started to collapse. Despite that, they decided to keep building and continued until the tower waseight storeys high. That took almost the next 200 years.

To prevent a collapse, they planned the next stages in a different way. They made the upeer part of the tower tilt the opposite way.

Tuscany Scenic Drive, Pisa Duomo

Campo dei Miracoli, one of Italy’s many UNESCO sites

In fact, the tower is not the only thing leaning on the square, everything else is leaning as well. These photos show you how much the cathedral Duomo and the Battistero tower also lean.

Campo dei Miracoli around the Leaning Tower

The field of Campo dei Miracoli has many additional great buildings. These photos illustrate the Campo Santo cemetery, being at the time of our visit carefully restored to stand in its place for another thousand years.

Campo Santo

The historic arcade of Campo Santo

Then we got our tickets to the Leaning Tower. The waiting time of an hour or two was not a problem. In the meanwhile we strolled around and looked at the other buildings.

Now we are in the tower:

Pisa street from Leaning Tower

Looking down from the Leaning tower of Pisa

After we had seen the other buildings lean, we felt that the Leaning Tower of Pisa is not leaning that much any more. It could be leaning much more, if they hadn’t done this:

Tuscany Scenic Drive Pisa leaning tower

The leaning tower of Pisa

In 1989 they noticed that the Pisa Tower was leaning all too much and in the state of collapsing.

They urgently closed the tower and started straightening it and they finally straightened it by 40 cm. Also they added steel to stabilize the tower.

This all took two decades and finally the tower is open to public again. But to prevent future problems they limit the number of visitors to access the tower at the same time.

Tuscany scenic drive Pisa statue

Romulus and Remus

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

The Campo dei Miracoli area is a UNESCO World Heritage Site.

Now about Lucca:


Tuscany scenic drive, the old Lucca marketplace

Our Tuscany scenic drive: stopping to look at Lucca

Before heading south we took a side trip to the historic town of Lucca, located 20 km north of Pisa. Lucca is encircled with a red brick defence wall on which you can walk all the way around the city. That makes a nice small city hike.

Lucca is a Roman city and consequently its marketplace Piazza Anfiteatro is shaped like an amphiteatre. The square used to be a Roman theatre, but all seats have little by little been replaced by yellow townhouses.

Tuscany scenic drive, a typical Lucca house wall

House windows in Lucca, Tuscany

Otherwise Lucca consists of narrow winding alleys that are good to walk, a number of historic palazzi and many museums. And of course piazzas and outdoor cafes:

Tuscany scenic drive Lucca street view

Tuscany scenic drive lunch in Lucca

Lucca: a piazza and trip lunch

Nothing tastes better on a sunny day than an Italian tomato bruschetta – and glass of a vino bianco for the non-driver.

The historic town of Lucca, Italy

The historic town of Lucca in the heart of Italy

From Lucca it is a pretty long drive to the first hilltop town, Volterra south of Pisa. You can choose between a busy, straight highway and a small, winding country road of which we chose the latter.


Tuscany scenic drive, a road trip in the Italian countryside

Our little Fiat 500 on a Tuscan country road


Tuscany scenic drive Volterra landscape

Tuscan fields seen from Volterra

Volterra is an old, originally Etruscan town sitting high up on a hilltop. Its citizens can enjoy fantastic views to the surrounding countryside, into all four directions.

Looking at this place I can now remember that our original plan was to make a bike trip to Tuscan hilltop towns. So good we noticed how high the Tuscan hills are and thus changed our travel plan. Getting up these hills on a bike would be a huge physical effort and right now we were not prepared for that.

Tuscany scenic drive, Volterra


Tuscany scenic drive, a Volterra street

Volterra, Tuscany

Volterra has narrow alleys on the top, built at a time when no cars existed. To avoid a nightmare, park below the city wall and walk to the center.

Tuscany scenic drive, the Volterra Twilight scene

The Volterra Twilight scene

This is what many people look for when coming to Volterra: the Palazzo dei Priori, the Twilight scene.

Volterra is a place where you could easily stay a night or two, but having booked a room in a private apartment in the next hilltop town San Gimignano we drove on.

Tuscany Scenic Drive: San Gimignano

Tuscany Scenic Drive San Gimignano hill view

Tuscany at its best: San Gimignano

So the next destination was San Gimignano. As the best preserved medieval city in Tuscany, we thought San Gimignano might be something for us. So we pre-booked a room at a San Gimignano bed and breakfast, located right on the main street Via San Giovanni.

It was a big family apartment where the hosts treated us well, except that understanding each other sometimes needed hands. Our balcony was to the inner court where we could see, and hear, their neighbors pass time with their big families and do some gardening.

Toscana Scenic Drive, San Gimignano hilltop town

Tuscany Scenic Drive, San Gimignano Duomo

Views of San Gimignano, Tuscany

San Gimignano looks like nothing has changed there after the middle ages. Just like elsewhere in Italy, the whole town is a pedestrian zone and cars are left outside the town gate.

But there is one thing that’s not like it used to be, San Gimignano towers. In the middle ages San Gimignano used to have 76 towers that were built to be private fortresses of wealthy local families. Time then destroyed most of these towers and only 14 of them remain.

Even with these 14 towers San Gimignano looks stunning. The towers look like skyscrapers, medieval ones. So San Gimignano is a medieval Manhattan

Tuscany Scenic Drive, a San Gimignano street

Tuscany Scenic Drive San Gimignano street view

San Gimignano street views

San Gimignano’s Piazza del Duomo has a palace with the oldest tower, and the next square Piazza della Cisterna has a well preserved 13th century well and one more medieval palace.

Tuscany Scenic Drive, an old Fiat

One more Fiat cinquecento

And then we found a really small car on the narrow lanes. An older model of Fiat than ours, and still smaller. Old Fiats like this are still common in Italy.

Toscana Scenic Drive, San Gimignano hill view

Tuscan countryside from San Gimignano

San Gimignano Vineyard Walk

Tuscany Scenic Drive San Gimignano

Walking in Tuscany: a vineyard on San Gimignano hills

What we didn’t know is that San Gimignano is a good destination for hikers.

There are many marked walking tracks in the hills around the city, all marked but not so well. We got lost.

Tuscany Scenic Drive view

Beautiful Italian countryside

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

A Tuscan vineyard

It was fantastic and we saw some amazing countryside we would not have seen otherwise.

Small farms, vineyards, cypress rows, sheep, and wineries. We partly walked along small country roads and partly on paths. But somewhere we got lost, and we got lost a second time, even when we had a map. There must have been a missing road sign, or a few.

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


Tuscany Scenic Drive San Gimignano country walk

A Tuscan country road and farmhouse

Finally back in San Gimignano, we counted we had walked more than half a 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 through which we walked for about three or four km.

Tuscany Scenic Drive olive trees

A Tuscan 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 there is a small village worth to visit, Monteriggioni.


Tuscany village

The Tuscan hill village Monterriggioni

Monteriggioni is located just off the main road to Siena.

Just like San Gimignano, Monteriggioni has thick walls and 14 towers from the 13th century. The towers were built to the hill to watch the whole area.

Tourists in a Tuscany village

A Tuscan window

Views of Monteriggioni, Tuscany

We have found another pretty town! As Monteriggioni is on the main road, tourist buses stop here. That’s why there are so many craft shops and cafes. The sleepy village wakes up every time a tour group arrives.

Crete Senesi hills, Tuscany scenic drive

Crete Senesi hills, Tuscany scenic drive

On the way to Siena there’s partly green forested areas and partly open landscape with rolling hills. This is the Crete Senesi area.

Then comes a bigger city and even that is located on the hilltop.


Siena Piazza del Campo

The Palio of Siena

The next hilltop is the home of the 14th century city Siena. It’s the commercial center of the region and much bigger and busier than the other hilltop communities we have been to.

Think about that, all places we have been to, except Pisa, have been on a hilltop.

Piazza del Campo

Siena, Piazza del Campo

Piazza del Campo, Siena

The core of Siena is the shell-shaped Piazza del Campo. The piazza is straight on one side and curved on the others.

What’s is even more special, Il Campo is divided into nine sectors. That’s because a council of nine used to govern Siena in the middle ages.

In Siena the principle is that all streets lead to Il Campo.

A number of elegant Palazzi surrounds the piazza and in the middle of it all is the fountain Fonte Gaia. The curved side of Il Campo is filled with pavement cafes and tourist restaurants.


Views of Piazza del Campo

Then there is a huge building that looks like a castle, the Palazzo Pubblico. It’s Siena’s 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 rest of Siena and the surrounding Tuscany.

The piazza is where the famous Sienese Palio is held each year in the summer. The Palio is a horse race where the jockeys are dressed in colored medieval clothes.

Siena Duomo

Siena Duomo

The Duomo of Siena

Another sight of Siena is the striped marble cathedral Siena Duomo that for me looks a 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 pillars in the interior are all black and white striped like liquorice. Go inside and see the amazing interior.

Siena Duomo

Beautiful places in Tuscany: Siena

After Siena it’s on the road again, stopping at whiles when you like the scenery at most. We stopped quite a lot before reaching Monticchiello, or next destination.

Driving in Tuscany

Driving in Tuscany

This is what the scenery around Monticchiello area is like – like a post card.

Tuscany hills

Rolling hills close to Monticchiello, Tuscany

Tuscany Scenic Drive: Monticchiello

Tuscany scenic drive: sitting at a Monticchiello cafe

The postcard-pretty hill village of Monticchiello

Monticchiello is the smallest hilltop village among the ones we went to. But certainly one of the prettiest. The place is remote, quiet and peaceful and no tourists were around in May.

We found a cafe with great views and good expresso. The cafe was inside the city wall and looked like a tiny castle.

Monticchiello view

Monticchiello flowers

Agriturismo holiday in Tuscany, Monticchiello flowers

Monticchiello flowers

Here are a couple more Montichiello views before it’s time to pass through the town gate, to complete our Tuscany scenic drive.

Monticchiello town gate

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

Pienza is a short way from Montichiello, provided you take the direct route along small unpaved country roads. The area is Val d’Orcia, a UNESCO listed river valley and real Tuscan countryside!

Tuscany scenic drive, Val d'Orcia vineyards

Val d’Orcia vineyards


Tuscany scenic drive Pienza

Visiting Pienza

And then, we are in Pienza. Pienza doesn’t make an exception, just like all other towns sit sits on a hill.

Pienza was built in the Renaissance style, by a Pope who was from the region. Of course not everything in Pienza is Renaissance, but despite that very charming.

Pienza has beautiful alleys with nice old street names, pretty squares and loads of flowers everywhere.

And the Tuscan scenery…

Tuscany scenic drive Pienza

Some fantastic Pienza scenery


Pienza, the center of Val d’Orcia

As the region’s tourist hub Pienza has many good restaurants and a good choice of accommodation. Almost all travelers want to visit and some of them stay for a while. As both Italian and foreign travelers love Pienza.

Tuscany scenic drive, a Pienza cat

A cat loving Pienza

Driving around in Tuscany

We stayed for days in the beautiful Val d’Orcia, in an agriturismo that I will tell you about in another post Italian Farmstay: Agriturismo Holiday in Tuscany.

During those days we went to see local sights, walked and biked and saw many more hilltop towns.

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

Tuscany scenic drive

The Tuscany scenic drive: whereto next?

Finally, from Pienza we took the straight road back to Pisa from where our flight left.

Hope you liked this journey, and if you have more time to travel, why not stay longer in Val d’Orcia, or head east. That’s a beautiful region too have I heard.

You might also be interested in these articles:

More about Tuscany:

Cinque Terre fishing villages:

Rome, 1,5 hours by train from Florence:

North Italy:

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  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.

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