I get many questions about the most beautiful villages in Tuscany, so I decided to share my insider knowledge with you in this post. Tuscany is gorgeous all year round, it is famous for its wine, picturesque rolling hills, locals who speak the “cleanest” Italian language, and, of course, its food, like beefsteak Florentine style and Ribollita – a vegetable and bread soup. These villages and small towns will give you the best atmosphere, views, and authentic Italian travel experience. Many of them have been chosen as movie scenes.
Montepulciano has become a very popular tourist destination since the filming of the famous film New Moon, sequel to the Twilight vampire saga. The movie gave it a well-deserved acknowledgment. It is a medieval town of rare beauty definitely worth visiting! A unique village with ancient churches, elegant Renaissance buildings, splendid squares, and small hidden corners.
Piazza Grande is Montepulciano’s living room, where people meet and go for a walk as their ancestors did for centuries. Here you can see Palazzo Comunale, a castle-like town hall with a clock bell tower rising in the center, that reminds of Florence’s Palazzo Vecchio. Climb the tower for a fabulous and boundless panorama of the Val d’Orcia and the Val di Chiana.
The unfinished Duomo, the cathedral, is quite spartan and stands out from other rich and beautiful buildings but don’t judge it from the outside: it has one of the most famous works of the Sienese painter Taddeo di Bartolo on the high altar.
Another well-hidden secret of Montepulciano is its underground city that goes back to the Etruscans. Under the street level, there are tunnels, caves, and Etruscan tombs. During the following centuries, they were used as cellars and even aqueducts. Today most of them belong to private families but you can visit some of them, like “La città sotterranea” and Cantina del Redi to see all the different layers of this gorgeous village.
San Gimignano is one of Italy’s best-preserved medieval towns. Since it is located on top of a hill, as you approach the village, you will see it from far away with its tall spires and Middle Ages atmosphere.
San Gimignano was an important trading city on the ancient pilgrims’ street, via Francigena, people who lived here were flourishing. Wealthy Italian families in the Middle Ages built towers as symbols of wealth and power, creating a competition that delights locals and tourists centuries after. The towers, medieval versions of skyscrapers, were once 72, but only 17 survived until nowadays. For this peculiarity, San Gimignano was named a UNESCO World Heritage Site.
The village today is enchanting. It is full of typical Tuscan picturesque charm, from its ancient protective walls to its amazing views and architectural details.
The wide Piazza Della Cisterna, surrounded by buildings, feels cozy despite its size. The Romanesque Cathedral with works by Ghirlandaio is a must-see, as well as the City hall with frescoes by Filippo Lippi and Pinturicchio.
If you don’t mind lots of stairs, you can climb to the top of the Torre Grossa for breathtaking views over the town and the entire valley with the famous rolling hills. Once you will visit the “city of the beautiful towers”, I guarantee, you’ll want to return!
Lucca is one of the most beautiful and beloved art cities in Tuscany. It can be visited in one day, but if you want to better savor it, stop for a few days or choose a base nearby to be able to visit it at least for a couple of days.
Lucca still keeps marks of its ancient history, like the traces of the Roman amphitheater visible in the form of Piazza dell’Anfiteatro. It also has kept various towers and villas built in the Middle Ages and Renaissance.
The walls surrounding the city have been exceptionally preserved despite the growth and modernization, unlike those of other countries in Tuscany, including Florence. They became a pedestrian area perfect for taking long and pleasant walks, creating a natural park with splendid views around the village that naturally leaves modernity outside.
Visit Lucca by bike to immerse in its medieval atmosphere and be sure not to miss any of its churches and towers. My only advice is to not visit it in the last days of October, when a huge Comics and Games event happens here, hiding most of its beauty with fair stands and crowds that come from all over Italy, unless you are interested in comics, of course!
Monteriggioni is an incredibly charming medieval village a few minutes from Siena and San Gimignano. With a simply stunning visual effect from above, it doesn’t seem real.
The village has never had the possibility to expand because its town walls measure only 570 meters (ca. 1870 feet). The village also has 17 imposing towers and only 42 inhabitants.
You’ll have the sensation of being out of the world: no traffic at all and a perfectly intact medieval environment will let you feel like part of a fairy-tale. Inside the walls, there are a few bars, one food shop, two restaurants, a hotel, and a typical products shop.
The center of the village is in Piazza Roma, which hosts the gothic church of Maria Assunta, built in 1219, definitely worth a visit. If you are in Monteriggioni at the beginning of July, you will be able to participate at the Medieval Festival, where everything is faithfully reconstructed, from the payment using the ancient coins to torches, candles, and even horses and donkeys as means of transportation. It might be a unique occasion for role-playing full immersion.
Pienza is a small village in Val d’Orcia, the southern part of Tuscany, not far from Montepulciano, considered the city of the best pecorino cheese.
The village is named after Pope Pius II, who was born here, Pienza means city of Pius. Enea Silvio Piccolomini, elected Pope Pius II in 1458, wanted to transform his birthplace, the anonymous village of Corsignano, into the ideal Renaissance town. He hired the best architects and artists of his time, creating a harmonious fifteenth-century town that remained practically unchanged over the centuries as a superb example of Renaissance architecture. Its historical center is a UNESCO World Heritage Site.
Pienza is considered to be a romantic city because of the names of its streets, like Via dell’Amore (love street) and Via del Bacio (kiss street).
When in Pienza, don’t miss Palazzo Piccolomini, where Pope Pius II used to live, the Cathedral built upon the remains of a Roman church, or Borgia Palace, now the Diocesan Museum. Like many other villages, Pienza offers breathtaking views to the nearby Val d’Orcia hills.
Siena is a must-see in the area, it is small, romantic, there are plenty of astonishing Medieval buildings and it is way less crowded than Florence.
Its main square, Piazza del Campo is considered one of Europe’s greatest medieval squares. You can enjoy it while sipping a coffee in one of the several bars located there.
Twice a year a horse race famous throughout Italy – Palio di Siena, happens in this square. Ten horses and riders, bareback and dressed in the appropriate colors, represent ten of the seventeen “contrade”, or city wards.
Don’t miss Siena’s magnificent cathedral, Duomo, and Mangia tower. To reach the top of the tower you have to climb 400 steps, but the views of the medieval building surrounding it and the countryside totally deserve it.
I already wrote about Arezzo here, it is another must-visit during your Tuscan trip. Arezzo was one of the filming locations for the 1997 masterpiece movie by Roberto Benigni: “La vita è bella” (Life is Beautiful).
Unfortunately, the medieval city centre was heavily destroyed during WWII, but a lot of monuments and works of art made it to nowadays. The historic centre can be reached by foot from the train station: walk along the pedestrian street Corso Italia, which will lead you to the main square, Piazza Grande. Benigni shot right here! Piazza Grande offers a mix of architectural styles, from medieval towers to the Renaissance and Gothic-Renaissance Palazzo Della Fraternita dei Laici and Palazzo delle Logge.
Every first weekend of the month, it hosts the famous antiques fair and it is also the site of the traditional Joust of the Saracens, a medieval tournament held for one Sunday in June and in September.
Many artworks in Arezzo are made by a famous medieval painter Giorgio Vasari, who was born here. You can even visit his house, planned and painted by the artist himself.
Like many Italian cities, Arezzo has the remains of a Roman Amphiteatre too, be sure you don’t miss it!
I hope you enjoyed our virtual Tuscan tour! Have you already been to Tuscany? Which village or small town did you like the most?