Tuscany Itinerary by Car

After so many years spent in this region and suggestions given to friends, I have finally decided to write a full guide for an ultimate Tuscany itinerary by car!

I’m going to start this trip from Pisa and from there I’m going to drive through the most beautiful landscape villages towns that Tuscany has to offer. This itinerary in this post is going to be for 7 days but you can easily change it to 5 days or to 10 days and I’m going to tell you in the end how to do that, but let’s jump straight into day one!

Day One: Pisa

So we are in day one when you arrive with your flight to the Pisa airport. Actually you may not know that the Pisa airport is the busiest in Tuscany with twice the flights that you have in Florence! What this means is that flying to Pisa is typically cheaper with more lowcost airlines.

Once you arrive at the airport, you can take the light rail train directly from the airport and in 5 minutes you are in the historical center, as easy as that! You don’t need to rent a car to visit Pisa, I will leave it for day two.

Local Tip: the Pisa Airport is located just within a 20 minutes walk from the historical centre. The light train, called PisaMover, is great if you have heavy luggage, otherwise take the short walk and save 8 Euros/person (cost of the shuttle ticket)

Leave your bag in your accommodation and go straight to visit one of the most iconic destinations in the world which is the leaning tower. Next to the leaning tower there is also the cathedral that you definitely have to visit.

Now an interesting fact about the tower is that it was leaning even during the construction! In fact, already when they built the first floor they realized it was leaning on one side, but what they did was not to actually take it down and rebuild it. It was to adjust and level the floor of the first level which makes the tower even more weird.

The tower is leaning because of the place and the soil where it was built and unfortunately the leaning increased through the years.

I still remember as a kid I was in Italy and there were so many plans on how to adjust the leaning tower to save the tower but to still leave some inclination (now about 5 m, or roughly 16 feet, out of the perpendicular) because you don’t want to go to Pisa to see a leaning tower which is not leaning anymore, do you?

Now don’t limit yourself to this iconic place because the historic center of Pisa is one of the most underrated centers I think of Tuscany. So walk back to the area and you will find the beautiful historic center where you can get lost for maybe a couple of hours.

Book one night only in Pisa because you want to pick up the rented car the following day and go to the next destination.

Local tip: If you’re not sure about the accommodation, I wrote a full guide about where to stay in Pisa, with the best areas and accommodations, otherwise just quickly check out La Corte di Lisa or Five Roses B&B

Day Two: Volterra and San Gimignano

We are in day two and it’s the time to pick up your rented car.

You have two options here: you can pick up your car from an office in the city of Pisa or you can go back to the airport which is just a five minutes ride or 20 minutes walk.

Local tip: I suggest rent the car at the airport because it’s going to be cheaper and also because at the end of your trip you can give it back and go straight to check in with your luggage.

Now that we have a car we can drive to our first destination which is Volterra, not too far from Pisa, and this is the first medieval village that you’re going to visit on this itinerary. Volterra is also off the beaten path which means you’re going to have more of a local experience.

You can venture inside the medieval walls and even visit the Roman theater which is over 2,000 years old! Volterra is a great place also to have lunch because most of the restaurants are family run, absolutely great food and they are more dedicated to local customers.

After lunch take your car and drive to San Gimignano that you may already know. It’s not definitely an offbeat and path destination but it’s as gorgeous as you may have seen in a few photos.

San Gimignano is considered to be a little bit of medieval Manhattan! 14 of its original towers are still standing actually in San Gimignano and you’re going to have a unique view of this medieval town with these towers coming up like mushrooms.

These towers are between 50 and 70 meters tall and if you ask yourself why actually there are so many towers in this small town, the reason was that in the 13th and 14th centuries the wealthy families used to build towers just to show off the money that they had.

Think of for example the Trump Tower in New York, and there was a race who was going actually higher and higher until the local council decided to stop this race because the towers were becoming unstable.

The tallest tower in San Gimignano was built in 1311 and the great thing is that you can still visit it today. So put it into your planning list because the view that you’re going to have from the top is absolutely gorgeous!

I personally suggest to have a stay in San Gimignano or if you want to save some money just book one of the agriturismo farm houses around San Gimignano where the bedroom maybe also with breakfast and dinner included, which is going to be a fraction in price of what you can find in San Gimignano.

Local tip: If spending the night in San Gimignano, have a look at Terra d’Ombra B&B. Otherwise, in the countryside, the Agriturismo Santa Croce is a winner

By the way, just a quick tip about the rental location in the Pisa airport: once you step out from the airport you turn left 100-150 meters and there is the shuttle bus stop that can take you to the rental car areas.

Otherwise if you turn right you can decide just to walk there which is absolutely doable unless obviously you have big luggage. The walk takes around 15 minutes and it’s 500m long.

Day Three: From San Gimignano to Siena through Chianti

Day three is dedicated to the trip between San Gimignano and Siena and we’re going to do this trip through the Chianti areas between Florence and Siena. The trip is going to be the highlight!

Local tip: The landscape you’re going to drive through will be absolutely amazing. To make the most, try to get the secondary road SR429.

Of course I highly suggest stopping by any winery that you find on your way, any viewpoint that you may encounter for beautiful photos over there. You can have lunch either in an agriturismo or go to Castellina in Chianti which is a town exactly in the middle between Florence and Siena.

It’s a beautiful medieval town with a lovely small square, restaurants with tables outside and that’s where you can have an easy deluxe lunch. And remember to take an espresso, a short coffee, at the end and not a cappuccino, something that the Italians never do!

You’re going to spend the full day along this trip. It doesn’t look like you’re going to drive a lot in kilometers but the roads are never straight and that’s why this area is so fascinating. You will arrive probably in Siena in the late afternoon.

Be aware that you can’t drive inside the old town or historical part of it. This is a ZTL area and only the people living there or having a business there can actually drive a car inside.

In saying that, there are a few parking areas, one of which is actually so close to the main square, super practical but also quite expensive. Another possibility is to park at the train station which is great value for money, but there are also other possibilities and for this reason I have written a guide on parking in Siena that you should check out if you plan to visit the city.

Book 2 nights in Siena. I have 3 suggestions here that you should check out: the Grand Hotel Continental, the Hotel Palazzetto Rosso and Hotel Italia

Day Four: Siena

On day four I suggest forgetting the car and just spending the day wandering around Siena. The first place you should go is in the main square Piazza del Campo.

This square has a sort of shell shape and this is the place where they do the Palio, one of the most famous horse races in the world. In fact, it’s the oldest continuous race in the world!

There are two horse races, one is on the 2nd of July and the other one on 16th of August, being the one on the 16th of August so popular that every Italian is in front of a TV watching it.

The race typically is only 90 seconds long but the whole environment around it is absolutely amazing. You may have seen actually in one of the 007 movies. If you’re there in one of those days you’re going to have one of the most unique experiences in the world, but in that case you should also book your accommodation very well in advance.

And when there is no Palio of course the square is covered with bars, cafes and restaurants where you can eat. There is also the beautiful Gothic Palazzo Pubblico on one side, so a great area really to wander around.

Besides Piazza del Campo I highly suggest also to visit the cathedral which is another unique place with its beautiful black and white marble facade.

And I forgot to mention an interesting fact about the Palio: the winner of the race is the first horse arriving to the finish line, doesn’t matter if a jockey is still on it, as it happened in 2023 (see video below)

Day Five: Val d’Orcia

Day five is dedicated to Val d’Orcia, one of the most scenic areas of Italy and that’s where you’re going to spend the next two nights. Add to your list towns like Pienza, a beautiful Renaissance town, then you can go to San Quirico d’Orcia.

You should add also Montalcino, Montepulciano – these are beautiful towns that will stay in your memory forever.

And between these towns you will have a landscape which is absolutely amazing! You may have seen part of these landscapes on the Gladiator movie with beautiful rolling hills and winding roads, incredible!

And this is also one of my favorite areas for wine in Italy, I must say. The Brunello di Montalcino is world famous but also the Nobile di Montepulciano, the Rosso di Montepulciano, and the Rosso di Montalcino are absolutely fantastic, great value for money.

And if you go to any trattoria or restaurant in Val d’Orcia, honestly even the house wine is absolutely beautiful and great value for money.

I personally suggest to stay in agriturismo in this area because the landscape around these farm houses are so typical of Tuscany.

Local tip: In Val d’Orcia you should check out the Dimora del Poggio in San Quirico and L’orto Delle Terme, two lovely accommodation in amazing locations.

Day Six: Cortona or More Val d’Orcia

On day six you have two options from your agriturismo in Val d’Orcia. You can make your way to Cortona, this is one of the oldest towns that you can find in Italy with over 3,000 years of history.

This town became so famous around 20 years ago thanks to the movie “Under the Tuscan Sun”. I definitely suggest watching it before you travel to Tuscany, it’s so beautiful.

I had the possibility to visit Cortona only few months ago and I enjoyed it so much. It was September so it was not very busy but it can get quite crowdy in July and August.

The other possibility is to explore more of the Val d’Orcia and I’m thinking here about two-three possibilities. The first one is the Fortezza di Radicofani which is a beautiful medieval fortress. From there you can decide to visit a couple of thermal baths

The first is the Bagni San Filippo, which is totally free to enter. The second is called Bagno Vignoni where you can have a luxurious treatment at the Posta Hotel.

Bagno Vignoni is a small village that definitely deserves a visit, with its beautiful central square a the thermal pool that, unfortunately, you can’t access.

Day Seven: Back to Pisa via Monteriggioni

On day seven you’re going to drive back to Pisa but on the way you should stop in Monteriggioni. This is a small village inside the round medieval walls in a pretty unique layout even in Tuscany.

There is a small square as you enter the castle and you have also the possibility to walk around the walls where you can have a fantastic view of the landscape around.

At this point, you may find impossible to actually compact this 7-day trip in just 5 days.

Well my suggestion here is to skip the trip along the Chianti area so go directly from San Gimignano to Siena, where you will spend only 1 night, and skip also the second day in Val d’Orcia.

It’s a huge pity in my opinion but if you have only 5 days unfortunately this is the best way to experience Tuscany in such a compact time.

On the other side if you have 10 days I probably would add either Lucca just to keep it in a loop and maybe also Florence.

The other possibility is to drive down in the southern part of Tuscany to discover three hidden gems: Pitigliano being the most beautiful one, called the Jerusalem of Tuscany, is absolutely stunning! From there it’s also an easy drive to the beautiful Saturnia which is another thermal spa area free of charge to enter.

If you want instead to add also Florence to your itinerary, you will need to budget at least another couple of days and in this case I personally suggest to give back the car at the airport and from Pisa take the 1 hour train to Florence because you won’t need the car in Florence, so you can save some money there.

In my opinion the best part of this itinerary obviously is the landscape you’re going to experience in Tuscany. It is true that cities like Pisa, Florence and Siena are absolutely stunning but visiting Tuscany without seeing actually its landscape is going to be such a big pity!