Tuscany road trip through 7 hidden gems

For the last 25 years I have been exploring this beautiful part of Italy and I have been always surprised that most travellers tend to visit the usual destinations complaining how popular (read busy) they all are. Siena is the classical example, but also Pisa, Cortona, etc.

For this reason I have decided to create this guide for a Tuscany road trip that goes through 7 higgen gems, 7 beautiful destinations that you may be able to share with just a bunch of other visitors.

You can start this itinerary of Tuscany from both Pisa Airport and Florence Airport. Although you could potentially do it with public transportation, I highly suggest hiring a car. You will save a ton of time and ultimately money too.

Monteriggioni

Once you pick up you car in either Pisa or Florence, drive straight to the first stop, Monteriggioni, where you can decide to spend also one night

Monteriggioni looks like something straight out of a medieval storybook. It’s a small town surrounded by massive stone walls and towers. You can walk along the old walls and get incredible views of the surrounding countryside. The town is very well-preserved and has a timeless feel to it.

Monteriggioni was actually featured in the video game Assassin’s Creed II! The designers were inspired by its medieval layout, so if you’re a fan of the game, this place is a must-see.

If you plan to book your accommodation in Siena, you can also think to stop in Monteriggioni for lunch and a nice walk around the main square and medieval walls. This town is certanly not as unknown as other places I have mentioned on this this Tuscan road trip, but if you decide to stay for the night, believe me, you will share the evening and with just a bunch of other visitors.

San Quirico d’Orcia

Next, we’re heading to San Quirico d’Orcia (60km or around 1 hour from Monteriggioni).

This little town in the heart of the Val d’Orcia has stunning views of rolling hills and cypress trees. It’s much quieter than nearby towns like Pienza or Montalcino, but just as beautiful. The main attraction here is the historic center, with its beautiful churches, including the Church of San Quirico, and the amazing Horti Leonini gardens.

If you can, plan a visit to San Quirico in June. That’s when the town turns back in time with the Festa del Barbarossa. The whole town dresses up in medieval costumes, there are flag-throwers, old-style taverns, parades… It’s like stepping into a movie set, but it’s all real. Super fun, especially if you’re there with kids or simply with a camera. 

San Quirico is also just 15 minutes by car to what I call the Gladiator Point, where Gladiator was actually filmed. It’s a great movie, by the way. You are also between Montepulciano and Montalcino, two of the best red wine areas in Tuscany. This basically means that even the house wine at €10 a bottle in the restaurants is gonna be awesome!

Both these areas have the Nobile (di Montalcino or di Montepulciano) wine, as remarkable as expensive, and the Rosso (red), once again great and amazing value for money. That’s what I usually suggest.

Sorano

Next, we’re going to Sorano (64Km or around 1 hour from San Quirico d’Orcia).

This town is built right into the rock, and it feels like a hidden treasure. The ancient buildings, churches, and fortress blend all together with the natural landscape, creating a unique atmosphere. Sorano is often called “The Matera of Tuscany” because of its similar cliffside positioning.

Sorano is home to an incredible underground network of tunnels and chambers, carved by the Etruscans more than 2,000 years ago. Some of them were used as escape routes, others for storing wine. Today, you can explore a few of them that stay cool even in the summer.

Pitigliano

The next leg is a short one to Pitigliano (10km or just 10 minutes).

This little town looks like it’s straight out of a fairytale, perched on a cliff made of tufa rock, basically limestone. It’s often called “Little Jerusalem” because of its Jewish heritage. Pitigliano’s streets are narrow, winding, and full of charm. The old stone buildings, especially the synagogue and the ancient Jewish quarter, really give this place a unique vibe.

Now, you might’ve heard of this town thanks to its white wine – which is pretty unique, especially in a region like Tuscany that’s mostly known for its reds. Pitigliano is actually famous for its “Bianco di Pitigliano,” a white wine made from grapes grown on tufa rock. That volcanic soil gives the wine a really distinct flavor. If you visit, definitely give it a try — it’s something special..

Montemerano

Next up is Montemerano (22km or around 30 minutes from Pitigliano).

This medieval village is tucked away in the Maremma region of Tuscany. What makes it special is its peaceful vibe and the stunning views of the surrounding hills. Montemerano is famous for its beautiful old town center, with its narrow streets and lovely piazzas.

The town is also known for its thermal baths. If you want to relax and unwind, you can visit the Terme di Saturnia, just a short drive away. The natural hot springs are famous for their therapeutic properties.

That’s why I usually suggest Montemerano to my friends who are looking for a quiet, relaxing place to stay with easy access to the springs. It’s not as touristy as some other spots in Tuscany, and it has all the charm and beauty you’d expect from this region.

Cetona

Let’s move on to Cetona (90km or around 1.5 hours from Montemerano).

This little village is set against the backdrop of the Cetona mountain, and it has a beautiful, peaceful atmosphere. The town is small, but its views are stunning. You can explore the narrow streets, and then head up to the top of the hill for some of the best views of Tuscany.

Cetona is known for its ancient caves and archaeological sites. The area around the mountain has been inhabited since prehistoric times, and you can visit some of these sites if you’re interested in history.

Another great finding in Cetona on my recent visit in late September was the presence of chestnut trees, which perfectly matched the local red wine, of course.

Anghiari

Finally, let’s visit Anghiari (100km or around 75-90 minutes from Cetona).

This hilltop village in eastern Tuscany is surrounded by thick walls and narrow streets. The historic center is well-preserved, and you can really feel the history as you walk around.

Of course, once again, the town is known for its medieval architecture and in this case also the incredible views over the Tiber Valley. Now, you may be already familiar with the Tiber River, which translates in Italian to Tevere.

This is the river that goes through the Eternal City of Rome, another city where I had the possibility to live for 4 years and I had such a great time there!

Here’s a fun fact: Anghiari is also known for the Battle of Anghiari, a big 15th-century fight that Leonardo da Vinci actually painted. The only problem? The painting got lost. So, if you happen to find it lying around, congratulations — it’s probably worth more than a truckload of Bitcoins!

Do it or not

If you’re looking for somewhere quiet and full of history, Tuscany has so much more to offer than the usual tourist spots.

This is an unusual itinerary that I love to suggest so you can experience the off-the-beaten-path Tuscany, a unique trip, where you will feel more like a local and not part of a tourist crowd.

But I am honest with you, don’t do it if you rely uniquely on public transportation. It’s going to be super hard, especially for destinations like Cetona and Anghiari.

Renting a car in Tuscany is going to help you big time.

Let me know in the comment section what do you think and if you have visited any of these places. I usually reply in no-time.