Tuscan towns: a road trip from Florence to Rome

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.!


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!


San Martino Cathedral in Lucca
The San Martino Cathedral, the “duomo” of 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.


View of the Campo dei Miracoli area in Pisa
Campo dei Miracoli in Pisa. You can see: the Baptistery, the Duomo and the leaning Tower in the back

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

Fields of wheat
You can understand why “Fields of Gold” by Sting was stuck in my head this whole trip!

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

Medieval buildings of San Gimignano
Snippet of the medieval 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!


A little shop in Monteriggioni
A little shop in 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.


The Piazza del Campo square in Siena with the Torre del Mangia
The impressive Piazza del Campo with its Torre del Mangia

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

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Responses to “Tuscan towns: a road trip from Florence to Rome”

  1. Tanja Avatar

    yes, I’ve been to all of these places and a few more. But this is the first time that I hear about Monteriggioni. it looks like you had a blast and you managed to see a lot

    Liked by 1 person

    1. Juliette Avatar

      Are there other towns in Tuscany you loved? Monteriggioni is a bit less touristic but it is really worth a visit, and the Medieval festival really made it special! Thanks for reading!


      1. Tanja Avatar

        Pienza,Montepulciano,Lucca.Siena is my favourite

        Liked by 1 person

        1. Juliette Avatar

          Wow amazing! Siena was indeed beautiful – much more than I expected to be honest!


  2. Lashaan Balasingam @ Roars and Echoes Avatar

    Awesome post, Juliette! It really does give us all a good idea of how much you can achieve in so little time and still love every single second of it all. I just know the journey itself was quite awesome for what it allowed us to discover! Thanks for sharing! 😀

    Liked by 1 person

    1. Juliette Avatar

      Thanks Lashaan! It was indeed a short time to see all of these beautiful places that would definitely benefit from a more thorough visit, but I loved that we were able to see so many diverse things!


  3. Rebecca Avatar

    I’ve only been to Florence and Pisa listed on here, but I’ve heard incredible things about Siena and the other smaller sites you mentioned. Your photos of the sand or rust-colored, centuries-old buildings show just how magnificent these places used to be, and that has translated over to the healthy tourism there is today. Keeping all of these sites in mind for a return trip to Tuscany someday!

    Liked by 1 person

    1. Juliette Avatar

      I would have loved to see more of Pisa but we were on a tight schedule! Siena is truly magnificent and the main square is absolutely stunning, the pictures don’t do it justice for sure! If you get to visit Tuscany another time (which I hope), I highly suggest the accomofation we stayed at! Thanks for reading!

      Liked by 1 person

  4. Bama Avatar

    So, so many pretty and interesting places to see and explore in just one region of Italy. You’re lucky to live just a few hours flight away from all these beauties! I really don’t know how I’m going to pick the places/cities I want to see for my first trip to Italy sometime in the future, because I want to see them all! 😄

    Liked by 1 person

    1. Juliette Avatar

      Oh, and we barely scratched the surface of that region, let alone the whole of Italy! I really feel very lucky to call this country one of my homes and that it is as you say so close to where I live, making it easier to visit several times! When you go to Italy I would definitely advise you to spend as much time as possible there, and then decide your itinerary based on your interests (art, history, nature, beaches, etc.)!

      Liked by 1 person

  5. travelling_han Avatar

    Every stop is just so beautiful 🙂

    Liked by 1 person

    1. Juliette Avatar

      I know! We were amazed at each of these cities that are so closeby but are yet so different! Thanks for stopping by!


  6. Pooja G Avatar

    Such beautiful stops, I can’t wait to visit Italy some day!

    Liked by 1 person

    1. Juliette Avatar

      I hope you’ll get to some day, it is truly a beautiful country!

      Liked by 1 person

      1. Pooja G Avatar

        Thanks and I can definitely see that!

        Liked by 1 person

  7. Stuart Danker Avatar

    You know how in Game of Thrones, you just know where the locations are based on the colour of the background? e.g. The Red Keep was always gloomy, and The North is always white. All your pics from this series look like they belong in the same theme, which is a mark of someone with attention to detail. And thanks for taking me to these places, which couldn’t be further from where I live!

    Liked by 1 person

    1. Juliette Avatar

      Thank you for your kind words, that means a lot! I’m glad you get to travel a bit through my post!


  8. Landious Travel Avatar

    Such beautiful pictures! I like all Tuscan towns 🙂

    Liked by 1 person

    1. Juliette Avatar

      Thank you! They all had so many different things to offer but were equally beautiful!

      Liked by 1 person

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