During our Italian holidays, we spent a week visiting the Tuscan Maremma and took the opportunity to explore some of the beautiful villages in this region.

These are small towns, each with its own unique charm and characteristics; all of them captivated us, and we decided to create an easy-to-consult list for you.

1. MONTEMERANO

Let’s start with Montemerano, a village in the province of Grosseto included among the most beautiful villages in Italy.

It is located on one of the countless Tuscan hills, and strolling its narrow streets felt like a true step back in time.

While walking along the main street, you’ll easily find the uphill path leading to Piazza Castello; when you reach the top, you’ll find an arch opening to a stunning square— a view alone worth the trip.

2. SOVANA

The second stop was the little town of Sovana, a town of Etruscan origin.

Before venturing into the historic center, we visited Sovana’s olive mill where we tasted the famous Tuscan olive oil and learned how it is produced.

Then we headed to the main street, where Sovana’s heart lies: the Palazzetto dell’Archivio.

3. SORANO

Not far from Sovana is Sorano, called the “Tuscan Matera” for the feeling it evokes upon arrival and for the extensive use of tuff stone in the construction of its houses.

Sorano is a winding tangle of alleys filled with many religious landmarks, including a Jewish quarter.

Try the “Sfratto,” a Jewish dessert that has become part of Maremma’s cuisine.

4. PITIGLIANO

The last stop of the day was Pitigliano, known as the “Jerusalem of Tuscany.” We arrived just before sunset.

We parked and sat on a bench to admire one of the most beautiful sights of the trip: the sun disappearing behind the walls — a moment not to be missed!

We recommend dining at Hosteria del Ceccottino to savor typical Tuscan dishes like crostini with lard and sausage and pappardelle with wild boar ragù.

After dinner, go back to the panoramic viewpoint to see the town seemingly suspended in midair.

5. CAPALBIO

Capalbio is located in a different area than the previously described villages, but if you’ve come this far intrigued by the Tarot Garden, don’t miss stopping by this village as well.

Once a coveted spot for nobles, wealthy landowners, and emperors, it is a true gem overlooking the Tyrrhenian Sea, with a historic center enclosed within double walls. You can walk the ramparts to enjoy views over the valley.

This is our personal Top 5 so far, but we look forward to discovering many more.