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.
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, 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.
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!
Pisa’s fruit and vegetable market
Delicious zucchini flowers for sale
.. 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.
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.
Then: a short walk north from the old town are the Campo dei Miracoli and the Torre Pendente, the Leaning Tower of Pisa:
Walking towards Campo dei Miracoli and the Leaning Tower of Pisa
Climbing the Leaning Tower of Pisa
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.
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.
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:
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:
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.
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:
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.
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:
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 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.
Our little Fiat 500 on a Tuscan country road
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.
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.
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 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.
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
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.
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.
Tuscan countryside from San Gimignano
San Gimignano Vineyard Walk
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.
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.
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.
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.
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.
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.
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
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.
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
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.
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.
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
This is what the scenery around Monticchiello area is like – like a post card.
Rolling hills close to Monticchiello, Tuscany
Tuscany Scenic Drive: Monticchiello
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.
Here are a couple more Montichiello views before it’s time to pass through the town gate, to complete our Tuscany scenic drive.
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!
Val d’Orcia vineyards
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…
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.
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.
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.
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