Tuscany 6-Day Road Trip

Road trip in Tuscany Italy

A 6-day road trip in Tuscany

Discover authentic Italian villages located on rolling hills while driving on scenic routes during this 6-day road trip in Tuscany. This gorgeous region is known for its landscapes, traditions, history, artistic legacy, and its influence on high culture. This made Michel and I very curious to explore this beautiful part of Italy! Let me take you along our road trip to Tuscany and show you our favorites places.

Preparation is the key to a fun, hassle-free road trip so you might want to check out my road trip checklist to make sure you have an unforgettable experience.

Highlights during our road trip in Tuscany

On the map below, I have pointed out all the highlights we visited during our Tuscany road trip. You can click on the individual red stars to open up a location. We booked our accommodation in San Rocco a Pilli and from there we drove to the various Tuscan towns. This road trip itinerary allows you to stay at one accommodation and you don’t you have to keep driving and sleeping in different places.

Day 1: San Rocco a Pilli   

From Rotterdam Airport we booked a flight to Pisa. From there we drove to a small Tuscan village San Rocco A Pilli where Michel’s family rented an accommodation called “Villa Poggio al Sole“. This villa is perfect when you are traveling with a larger group of people. It has two floors, several bedrooms and bathrooms, a fully furnished kitchen, and awesome outdoor space (an outdoor dining area and a huge garden with hay bales!).

For us this turned out to be the perfect base to plan our road trip around. We were looking into driving about 30-60 min. in between each location, which is totally doable, and most scenic roads are pretty quiet!

Road trip in Tuscany Italy San Rocco a Pilli

The photo above is taken in the backyard of Villa Poggio al Sole. The 360° view and warm color tones stood out to me the most. We could even spot Siena in the distance! San Rocco a Pilli is very tiny (about 600 inhabitants) and not so exciting, but we had an awesome first impression of the hilly Tuscan landscape.

Day 2: Montalcino, Bagno Vignoni and Pienza

It was time to hit the road! Michel and I got up early in the morning and left after breakfast to visit Montalcino. I think we drove for about 15 min. when I already asked Michel to stop the car (a girl can be excited, right?). Coming from the Netherlands, which has no hills, the Tuscan countryside was such a nice change!

Road trip in Tuscany Italy

During the rest of our drive towards Montalcino we saw lots of solitary ochre houses, giant cypresses, vineyards and olive groves. This was everything I imagined Tuscany to look like before we left…

Road trip in Tuscany Italy Montalcino

In the breathtaking Val d’Orcia Natural Park you will find the beautiful medieval hill town Montalcino. This village is a wonderful place to check out charming arts and crafts shops, cafes, restaurants and wine bars. It’s renowned all over the world for the production of its precious Brunello red wine. So if you wish to take home a bottle of superb wine, this is definitely the place for you.

Road trip in Tuscany Italy Montalcino

BUT Montalcino is not just wine, it is also very rich in artistic treasures. The historical center is dominated by an impressive fortress. The views from its ramparts are really spectacular! Another landmark is the tall clock tower that graces the city’s town hall Palazzo dei Priori. Also, worth visiting is the Palazzo Vescovile and the churches of Sant’ Agostino, Sant’ Egidio, and San Francesco.

Road trip in Tuscany Italy Montalcino

After a nice morning stroll in Montalcino we drove to the Abbey of Sant’Antimo. This abbey is one of the most beautiful architectural jewels in Romanesque style that still exists today. Make sure to check out the Carolingian Chapel, the crypt, the tribune, the monastic pharmacy and St. Benedict’s herb garden.

Road trip in Tuscany Italy Abbey Sant'Antimo Montalcino

Bagno Vignoni
After lunch we visited the ancient village of Bagno Vignoni, which is located on a hill surrounded by the Val d’Orcia river. This village is a little different from the others: what in traditional towns is a main square, in Bagno Vignoni is a pool from which bubble up a number of hot springs!

Road trip in Tuscany Italy Bagno Vignoni

You are not allowed to bath at the main square pool, but if you go down to the Parco dei Mulini you can relax at a spring of naturally hot water (free entrance). So, don’t forget to bring your swimsuit and a towel! Because of the hot weather we didn’t feel like taking a warm swim, but I bet it’s lots of fun.

Road trip in Tuscany Italy Bagno Vignoni

In the late afternoon we arrived at the home town of Pope Pius II: Pienza. The city center is a UNESCO World Heritage site, because its urban concept was an example to many other European cities. It’s considered to be the ‘ideal’ Renaissance town. Isn’t that just so cool? To top it off this village has ‘lovely’ street names such as Via dell’Amore (love street) and Via del Bacio (kiss street). How romantic…

Road trip in Tuscany Italy Pienza

The main sights include the cathedral, Piazza Pio II, Palazzo Piccolomini, Palazza Borgia and Palazzo Comunale. Besides that, the town is full of small charming shops selling various types of pecorino (cheese) from fresh to aged. Other typical local products include fine wines, spices and pici (handmade pasta). For all you foodies out there: live your heart out!

Road trip in Tuscany Italy Pienza

Day 3: Abbey of San Galgano and Siena 

The next morning, we explored another really old abbey!

Road trip in Tuscany Italy Abbey San Galgano

The 13th-century Gothic abbey of San Galgano, which has two sights of interest you don’t want to miss:

  • The monastery including the enormous church without a roof
  • The sword of San Galgano (embedded in a stone) which represents a symbol of peace
Road trip in Tuscany Italy Abbey San Galgano

Start your tour by walking through the beautiful alley of cypresses towards the monastery. Then take a right and follow the signs which will lead you to entry of the abbey. After visiting the abbey take the indicated path to check out the sword. Seeing it somehow really reminded me of the stories of King Arthur, haha. It felt like I was right in the middle of a movie set!

Road trip in Tuscany Italy Abbey San Galgano

Later that afternoon we arrived in Siena. This UNESCO listed city is famous for its art, museums, cuisine, characteristic narrow streets and the Palio. The Palio (famous horse run) takes place two times every Summer and is even featured in a James Bond movie: Quantum of Solace.

Road trip in Tuscany Italy Siena

There is A LOT to see in Siena, so here’s a list of some of the major highlights of this lovely cozy town:

  • Piazza del Campo (one of the biggest medieval squares in the world)
  • Torre del Mangia (this tower is 88 meters high and has 400 steps!)
  • Cathedral (beautiful interior full of esoteric symbols and religious stories)
  • Baptistery (gorgeous frescoes)
  • Complex of Santa Maria della Scala (filled with museums and splendid monumental areas)
  • Public Palace of Siena (all the rulers of Siena lived here and now it’s a civic museum)
  • Church of San Domenico (cool architecture and check out the relic of Holy Head of Saint Catherine)
  • Siena Duomo (a majesty of cathedral with a stunning details and a mosaic floor)
Road trip in Tuscany Italy Siena

Day 4: Florence and Monteriggioni

Florence is the capital city of Tuscany and its museums, palaces, and churches house some of the greatest artistic treasures in the world.

Road trip in Tuscany Italy Florence
It’s also the most populous city of this region. Although we left early in the morning we got swamped by tourists. If you’re not into huge crowds I would maybe avoid visiting Florence during the Summer season. Everybody wants to have a glance at this magical city.
Road trip in Tuscany Italy Florence

The most important sites are the cathedral, the baptistery, the Uffizi, the Bargello, and the Accademia. We spent the morning wandering the streets and walked across the Ponte Vecchio.

Road trip in Tuscany Italy Florence

Also, we passed many impressive churches such as Santa Maria Novella, Santa Croce, and the library of San Lorenzo (check out Michelangelo’s work!). All absolutely beautiful! Are you looking for an enchanting view of Florence? Check out the Boboli Gardens, climb the hill to the church of San Miniato al Monte, visit the Florence Duomo or the Piazzale Michelangelo.

Road trip in Tuscany Italy Florence

Because of the crowds (we did not expect it to be SO busy, because it was really hot that day) our visit was a little less fun I admit. There were long waiting lines everywhere and it was a challenge to even find a lunch spot. But overall, we had a good time and I would love to go back off season. 

Road trip in Tuscany Italy Florence

After Florence we found much needed peace in the cute small town of Monteriggioni. This is one of the most impressive walled towns (with a total length of about 570 metres!) located on a natural hillock. You can spot its 14 mighty towers from miles.

Road trip in Tuscany Italy Monteriggioni
The village within the walls revolves around a central piazza, home to the church of Santa Maria Assunta. This town was such a nice relief! We hardly saw any tourists and exploring the streets in this town felt like being in a different era.
Road trip in Tuscany Italy Monteriggioni

Day 5: Certaldo, Volterra and San Gimignano 

We started our day with a (very strong – how the Italians like it) cup of coffee in Certaldo. This is the perfect place to start your day while enjoying the relaxed atmosphere and beautiful views.

Road trip in Tuscany Italy Certaldo

The town can be divided into two areas ‘Certaldo Bassa’ and ‘Certaldo Alta’. The first part is the newest area of the town, located in the lower zone, while the latter is the old part where you can find important sights like Palazzo Pretorio (Priori Palace), Church of SS Jacopo and Filippo, museum of sacred art, and Casa Boccaccio.

Road trip in Tuscany Italy Certaldo

Later that morning we continued our road trip to Volterra, where you can find lots of architectural heritage (from the 4th through 6th centuries BC as well as the Roman era). And the cool thing is you can still see traces of all the past eras today. No wonder this ancient town got featured in one of the scenes of The Twilight Saga: New Moon.

Road trip in Tuscany Italy Volterra

The enormous Medici Fortress stood out the most to me, because of its location (on a hilltop) and its impressive size. You definitely won’t get bored in Volterra, because there are numerous museums to check out: the Etruscan Museum, the Pinacoteca, the Museum of Sacred Art, and the Alabaster Ecomuseum. Don’t forget to make you way out of the historic center to have a look at the Roman Theatre and the ruins of the Etruscan Acropolis.

Road trip in Tuscany Italy Volterra

San Gimignano
This amazingly preserved town, San Gimignano, is famous for its fascinating architecture and towers that rise above of all the other buildings. The patrician families built around 72 (!) tower-houses as symbols of their wealth and power.

Road trip in Tuscany Italy San Gimignano

Sadly, only 14 towers have survived. Check out the view of the city on the surrounding valley or one of these highlights:

  • Piazza del Duomo (spot the cathedral and the various incredible towers)
  • Porta San Giovanni (impressive ancient door – yes, a door – and it’s one of the most beautiful doors of Italy)
  • Piazza della Cisterna (square with a big cistern that was built in 1287)
Road trip in Tuscany Italy San Gimignano

Day 6: Pisa, Follonica, Torre Mozza and San Vincenzo

On our last day, we visited Pisa very briefly in the morning (about one hour). I really wanted to see the Power of Pisa in real life, lol! Since we decided to take a coast route later that day we didn’t have much time in Pisa’s city center. In the afternoon we drove to see several beaches in Follonica, Torre Mozza and San Vincenzo. I can highly recommend ending your road trip to Tuscany relaxing at the beach.

You can also decide to spend more time in Pisa (half-day) and combine this with one beach site. I would choose Torre Mozza because it’s less touristy and calmer compared to the other two. Or just completely skip the coast and enjoy a full day in Pisa to visit all major highlights. 

I can’t wait to go back to Tuscany someday! This beautiful region really surprised me and was more beautiful than I imagined it to be. 

Tuscany Road Trip Pisa

Psssst, would you like to see more dreamy shots of Tuscany?

Then watch my Instagram Tuscany story for more beautiful videos of ancient towns, amazing view points while road tripping, delicious food, and more!

Free Adobe Preset “Summer in Tuscany”

Back home I started to edit all of our photos in Adobe Lightroom. While editing I tried to create a warm color pallet that would work for many different subjects. Find out how I edited all the photos above by using just one versatile preset right here. It’s totally FREE!

Road trip in Tuscany ItalyRoad trip in Tuscany Italy

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