In July, I went on a trip to Italy that started off with a fantastic stay in Florence, followed by an amazing road-trip through Tuscany, while we made our way to Rome. Our time there was limited as we only had a bit less than two days, so we had to make the most of it and, through thorough research and asking around, we selected what we thought were the best Tuscan towns to check out during our road trip.
I know this is not ideal, and in a perfect world we would have had a whole week – or even more – to spend in Tuscany and explore its towns, but sadly nothing in this world is perfect and this meant we only saw some places superficially, but we were okay with that. We still managed to eat something in each of these places (lunch or a gelato) and to have a walk around for a couple of hours.
So, without further ado, here are the towns and cities we saw on our road trip through Tuscany! You can obviously use this little list and follow our itinerary, or get inspired by it to create your own, select the place(s) you want to see the most, etc.!
Florence
I talked about it in this post right here. I would say that unless you only want to focus on small towns, it is absolutely a must-do. You could spend a week there and still have plenty to see!
Leaving Florence, instead of heading straight South in the direction of Rome, we decided to head West for a bit to check two iconic Tuscan towns, that are very close yet pretty different!
Lucca
Lucca is a town with Roman origins, but it is also known for its fortified walls erected during the Renaissance, for its particularly well-preserved historic centre and for its many churches (it is called “the city of hundred churches”). It is also where a comics festival takes place each year, and its medieval streets suddenly get filled with cosplayers – it is definitely something quite unusual.
This was our first stop and we were starving so we first stopped to eat delicious “sandwiches” with local types of ham called biroldo and finocchiona. While we were eating, we followed an itinerary we found on our guidebook that would take us to some of the main landmarks of the city, including the Torre dei Guinigi, a medieval tower on the top of which grow beautiful trees, and some beautiful churches, like the Duomo of Lucca and its stunning façade of pink, white and green marble, that inevitably reminded me of Florence’s own Duomo.
Pisa
Pisa is another stunning city located in the western part of Tuscany. It was an extremely wealthy town from the 11th to the 13th Century, which is pretty obvious when you see the beautiful buildings erected at the time. You can see the most famous landmarks of Pisa in an area a bit outside of the city centre called “Campo dei Miracoli” (the Square of Miracles).
Since we didn’t have much time, we decided to only check out this area so that we would at least see the main landmarks. There, you can admire the Baptistery, the Duomo (yes, another one!), the Camposanto (a graveyard) and, of course, the world-famous leaning Tower. We grabbed an amazing ice cream (truly fantastic!) and walked around the square, admiring the intricate details of these stunning buildings. Fun fact: they all lean, but it is more obvious for the Tower due to its shape, of course!
The Tuscan country side and stop for the night
While we were heading South to reach our accommodation, we passed through some truly postcard-worthy Tuscan landscapes of rolling hills of golden wheat, fortified towns on top of little hills, overlooking the countryside dotted with cypress trees. We stopped here and there to take some pictures but soon realised we needed to hurry to reach our accommodation.
We arrived at sunset in this stunning place, in the middle of the Tuscan countryside, next to Casole d’Elsa. The magical touch was provided by a flock of sheep walking by with their little bells ringing and the golden sun setting. Our host was absolutely amazing and while showing us around, he also recommended us a nearby restaurant where we ate a fantastic Florentine steak. After a delicious dinner and some star-gazing, we finally went to bed, tired after this long day of exploring under the sun!
San Gimignano
On the next morning, our day of exploring started with the typical Tuscan town of San Gimignano, which is becoming increasingly famous – and indeed it was quite crowded! Located on the top of a hill and circled by medieval walls, San Gimignano is also a UNESCO World Heritage Site. It is famous for its medieval architecture, its towers and its wine.
There, we just walked around the centre and stopped for an ice cream, that was apparently the “World’s best gelato” for several years – it surely did not disappoint!
Monteriggioni
Not so far away from San Gimignano, Monteriggioni is a less touristic medieval town built on top of a hill in a strategic position. It is also famous for its many towers and for its medieval vibe, with small shops and narrow streets. Every year, a medieval festival is organised there, and the streets fill up with people in period costumes, bringing the visitors back to the Middle Ages.
Our visit was during the festival so we got a chance to see how the town really was during the Middle Ages and could try some traditional food, check out some shops and just walk around in the enchanting atmosphere created by this lively atmosphere.
Siena
If you liked the medieval aspects of all these towns, you will definitely love the city of Siena. This city is mostly famous for the “Palio”, a horse race taking place in the city’s main square known as Piazza del Campo, but it obviously isn’t limited to that.
In Siena, we walked around the narrow streets, taking turns here and there, and stopping at landmarks such as the Duomo and the Palazzo Pubblico, with the adjacent Torre del Mangia, which is the second tallest tower of Italy, that you can also climb to get a stunning view of the city.
At the end of this little walk, we headed back to our car and went straight down to Rome for the biggest portion of our time in Italy!
Other places worth mentioning:
There are obviously countless of other amazing things to see in Tuscany, and we had to make some sacrifices and skip some places, even though they were on our list initially. I don’t really like to talk about things that I have not seen or experienced, but in case you’re looking for inspiration for your next trip, here are some ideas of things to do in Tuscany:
- Tuscan towns: Volterra, Collodi, Montepulciano, San Quirico d’Orcia, Colle di Val d’Elsa
- Natural wonders: Garfagnana valley, the thermal pools of Saturnia
- A tour in the Chianti area (with wine tasting)
- Olive oil tasting/visit of a factory
Even though we didn’t have much time, this short itinerary still allowed us to see bigger cities and world-famous landmarks, get a taste of some Tuscan specialties and walk around smaller towns, while admiring the countryside. These are also places that I would really recommend to anyone visiting Tuscany, as long as you keep in mind that to see all of these in a short amount of time you have to skip some visits and be very efficient!
Have you ever been to Tuscany?
Other posts about Italy
A glimpse of Florence: things to do in less than two days
– A week in Italy after the lockdown
– My favourite things about summer in the South of Italy
Sunny Days with Juliette 
Leave a Reply