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: 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
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!
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!
Pisa vegetable market
Zucchini flowers for sale
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.
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.
A short walk north of the city are the Campo dei Miracoli and the Torre Pendente, the Leaning Tower of Pisa.
Towards Campo dei Miracoli, Pisa
The Leaning Tower of Pisa
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.
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.
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.
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.
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.
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: 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.
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.
Driving in Tuscany: our Fiat 500
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.
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.
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.
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.
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.
Tuscan countryside from 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.
We got a walking map from the tourist office and took a 15 km loop trail to walk the countryside and vineyards.
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.
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.
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.
Crete Senesi, Tuscany road trip
On the way to Siena there’s a lot of green forest and partly open landscape with rolling hills.
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.
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.
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
This is what the scenery in the Montichiello area is like – looks like Tuscany in post cards.
Rolling hills of Tuscany, Italy
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.
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.
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!
Val d’Orcia vineyards
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…
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.
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: 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:
- On an Agriturismo Holiday in Tuscany: how to arrange a Tuscan farm holiday and what a Tuscan agriturismo is like.
- The Best of Florence in One Day: on your trip around Tuscany you should spend at least a day in Florence.
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: