Driving in and around Tuscany: One Week Itinerary

Going on a trip to Tuscany is the promise of a captivating journey, in the middle of hilly landscapes and picturesque scenery, designed perfectly as if in painting. It also means discovering the rich cultural heritage of this region of central-western Italy. Whether it is for its gastronomy, which can satisfy all taste buds, or for its villages, which are among the most beautiful in Italy, Tuscany is to be seen and experienced. I take you to discover Tuscany in my own way….

When I think about Tuscany…

 I see stretches of hilly land as far as the eye can see, wheat fields, vines, all forming a gradation of orange, green and yellow colours.
 I feel the warmth of the sun on my skin and the warm air blowing through my hair. I smell the smells of pines and cypresses, the wine that has just been served, and the truffle that has just been picked.
 I hear the bell tower ringing with all its strength, I hear the birds singing, the sound of the coffee machine making an espresso and the sound of vespa and minivans in the alleys of a medieval village.
Yes, Tuscany quickly takes me to an enchanted universe that seduces me.


I discovered Tuscany when I was still very young, and since then I have returned several times. For the last two years, it was autumn, with its orange tones and its very cool mornings. In this article, I take up my favorites, my encounters and my discoveries of a region that can be visited for a long weekend or several weeks, during all seasons. At the end of the article, I share with you my good addresses for eating, sleeping and all the advice you need to prepare your trip. A presto !

Driving in and around Tuscany

In this post, I am sharing my favorites and my discoveries driving in and around Tuscany. At the end, you can find all the best adresses for eating, sleeping, and everything you need to know to prepare your trip.

Visiting Tuscany : Itinerary & Tips

Carte Toscane


Rural Tuscany

The beauty of Tuscany is its landscapes, with its hilly fields and cypress paths. This rural Tuscany amazes me so much the colours are beautiful and the landscapes seem to have been drawn perfectly and meticulously detailed.
What you shouldn’t miss:

  • Val d’Orcia, A vast valley south of Siena, a UNESCO World Heritage Site: it changes colour with the seasons, with its most wonderful landscapes in June when the wheat fields are yellow.
  • Vallée du Chianti, considered the heart of old Tuscany, it presents mainly valleys of vines and has given its name to the famous wines.
  • There are many small medieval villages, often perched at the top of a hill, overlooking the valley. I’ll tell you more about it below….

To discover rural Tuscany, we have chosen to sleep in Borgo or Agriturismo style accommodation in the middle of nature and we have chosen roads parallel to expressways, to be able to discover the countryside and the small villages along the road.

Driving through scenic roads

We drove away, which allowed us to move around freely and take as many breaks as we wanted. What I particularly appreciated were these picturesque landscapes. Don’t hesitate to stop. A real pleasure. Not all roads are pleasant, but the most emblematic roads that have made me fall under the spell of Tuscany are:

  • The road between San Gimignano and Volterra (SR68): it’s an incredible spectacle!
  • The road between Montepulciano and San Quirico (SR146): it is one of the most photographed roads in Italy, probably one of the most beautiful too. The road crosses the hills, cypress alleys, agritourism, passing in front of the Chapel of Vitaleta and in front of the Podere Belvedere. In short, there are not many kilometers but we took a few hours counting all our photo stops and our “wow, let’s stop 5 minutes here”!

Medieval towns

There are many villages to visit in Tuscany. Some are more authentic and better known than others. When you only spend a few days in Tuscany, it is better to know in advance where to go and what you want to see, but if you spend more time in the region, I really advise you to stop where you like and you could make some very beautiful discoveries, as it was the case for me during my trips.

Here is the list of the villages that seduced me the most, starting with the most famous ones:

  • San Gimignano
  • Volterra
  • Montepulciano
  • Pienza
  • San Miniato
  • San Quirico




Focus on Pienza

Pienza is a small medieval village with a view of the Val d’Orcia. The village is not very big but we enjoy strolling through its few streets with all these small shops and restaurants. Behind the Renaissance Square, the narrow streets lead to a viewpoint from where you can see the Orcia Valley and its multicoloured carpets of land. In Pienza, all the stone houses are nicely decorated and decorated with flowers. It is a pleasure for the eyes, and the taste buds too, since we tasted the famous “bistecca alla fiorentina” (a piece of meat weighing more than a kilo, which melts in the mouth) in one of these restaurants (La Buca delle Fate) and without a doubt, it was one of my favourite moments of the trip, because the meat was so melting and tender. It is also the ideal place to buy some souvenirs – they will be cheaper than in big cities.


Focus on Montepulciano and its vino nobile

A few kilometres from Pienza, there is another medieval village perched at the top of a hill: Montepulciano. The village is very small, but very picturesque and once you reach the top you are greatly rewarded by the magnificent view!
Below the village, we find the San Biagio cathedral, which is quite impressive given its size. Once again, we found a nice and very good Tuscan restaurant (La Briciola).
On the road between Pienza and Montepulciano, I advise you to stop at one or the other vineyard that offers to do a wine tasting. This is a fairly touristic activity but it allows you to get to know a family or a small company that makes wine and then taste some local wines. Montepulciano is renowned for its vino nobile, the wine of the region, an AOC wine.
It is quite possible to find free tastings (and only pay for glasses of wine consumed). The visit is in Italian or English.

If you like goat cheese, it is also the perfect place to buy percorino or ricotta di pecora (goat’s cheese), which are specialities of the region. There are many in the farms or agriturisms in the area.

Florence – Firenze

The city of Florence deserves to be spent several days there and I should write a few pages on this blog only to try to discover it and transmit its beauty and richness. The city is not very big, it is easy to discover by foot.
I strongly advise you to take the time to visit Florence and its various museums. Here is a (very short) list of things to see in Florence:

Ponte Vecchio
  • Piazza del Duomo : we find the Brunelleschi dome, symbol of Florence, the Baptistery, the cathedral of Santa Maria del Fiore and the Campanile di Giotto. To visit the cathedral, the dome, the bell tower and the baptistery: combined ticket (about 15€) – I advise you to book it on the internet in advance. To book here
  • Ponte Vecchio (picture on the right)
  • Santa Croce : craftsmen’s quarter and craft shops
  • Panoramic view of Florence: Climb up to the Church of San Miniato al Monte, at Piazzale Michelangelo.
  • The most famous museums: Uffizi Gallery, Palazzo Vecchio, Academy Gallery.


Siena is one of the many jewels of Tuscany that is worth a visit. The historic centre of Siena is practically pedestrianised and it is really pleasant to stroll through all the alleys to discover monuments and churches to visit. We take an ice cream in one of the many gelateria and land in Piazza del Campo. Then we continue towards the Duomo (which we must visit at all costs!), before going to take an aperitivo.


In brief

There are of course other places to discover in Tuscany. I am thinking of Pisa, Lucca, Lucca, and about ten other villages. And then the whole west coast, as well as the Elba Island… Visiting Tuscany is also about discovering its culture, its gastronomy, its way of life and its inhabitants. People will always be willing to help you and tell you about their lives if you give them the opportunity.

Tips to prepare your trip to Tuscany

All you need to know to prepare your travel to Tuscany

Good places to eat

  • Near San Miniato: Casa Masi
  • In Montepulciano: La Briciola (la bistecca fiorentina is delicious)
  • In Montichiello: Osteria La Porta
  • In Pienza: Trattoria La Buca delle fate (To try: la Bistecca fiorentina and the Picci)
  • In between San Gimignano and Volterra: Osteria Villa Felice (wonderful view)
  • In Pisa: To find a restaurant or a place to eat “not too touristy” you must absolutely leave the “Tour de Pisa” area. Go to the historical district, towards the river and the Corso Italia. See on the map here.

Where to go for wine tasting ?

For a wine tasting: Chianti region and near Montepulciano (we went to the Azienda Agricola Canneto)

Good places to sleep

  • To visit the North of Tuscany, I recommend sleeping in the area between San Miniato and Florence: Our stay: Borgo San Benedetto here
  • To visit San Gimignano, Volterra : Fattoria Voltrona here
  • To drive around Val d’Orcia : Borgo Sant’Ambrogio here

The main airports are those of

  • Pisa (International airport): practical for visiting northern Tuscany (Pisa, Lucca, Florence and the Chianti region)
  • Perugia (in Umbria): practical for visiting southern Tuscany and the Val d’Orcia

The car: Ideal for travelling in Tuscany. Having a car allows you to combine cities and landscapes of nature. The roads are passable, so there is no need for a big car: a Fiat 500 is more than enough (and makes parking easier, too!).

Renting a car is not very expensive. We have rented with Fire Fly and Inter Rent at Pisa Airport (car rentals are 5 minutes drive from the airport and a free shuttle bus takes us there – at the airport exit)

Public transport (train and bus) is not very expensive and connects the main cities (Pisa – Florence – Siena). Not practical to stay in an agritourism outside urban centres.

We eat extremely well in the Tuscan region. Among the typical dishes to taste:

  • The truffle (near San Miniato)
  • Picci (typical pasta from the Val d’Orcia)
  • La bistecca alla fiorentina
  • And of course, the wine (from the region)!



Have you ever been to Tuscany?
Do you have any recommendations?  Leave a comment
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