town of lucca

Beautiful Towns and Villages to Visit in Tuscany

Visitors to Tuscany come for many reasons. Many come in search of fine art and medieval history, others to explore the extraordinary countryside and its rolling hills. Food lovers visit Tuscany to enjoy the wonderful cuisine and famous wines. Summer vacationers the beautiful beaches and islands. Students come to learn the Italian language and culture. Whatever the reason, Tuscany offers something for everyone.

Much more than the home of Florence or of rolling countryside, Tuscany is also the home of some of Italy’s most beautiful, and fascinating towns and villages. Choosing which typical towns and villages in Tuscany to visit on your holiday can be challenging, especially if you want to stay off the beaten track. Whether you’re considering a day trip from Florence, or just hoping to make your base in Italy somewhere off the beaten path, here are our top towns and villages to visit in Tuscany.

Lucca: Tuscany’s Less-traveled Gem

town of Lucca is one of the Beautiful Towns and Villages to Visit in Tuscany

Lucca is refreshingly – and surprisingly – not on the main tourist trail. Lucca sits on the Serchio river, making it one of the few Tuscan towns and villages that does not occupy a hilltop position. Graced with medieval streets and a ring of Renaissance-era fortification walls — today, a bike and walking path — Lucca’s architecture is some of the most exquisite in Tuscany. If you think Florence’s Duomo is elaborate, just wait till you see Lucca’s Duomo or its Church of San Michele in Foro, which look like they were created out of icing! The Duomo San Martino houses many historical treasures, such as Tintoretto’s Last Supper and the Tomb of Ilaria del Carretto. Don’t miss the Piazza Anfiteatro, a ring of medieval buildings on the site of an ancient Roman amphitheater (some of it still remaining). Here is also where the composer Giacomo Puccini was born.

Pienza: the jewel of the Val d’Orcia

pienza in the val d'orcia is one of the Beautiful Towns and Villages to Visit in TuscanyThe Val D’Orcia (Valley of Orcia) South of Sienna is the absolute epitome of what we all expect Tuscany to look like … a landscape of green valleys surrounded by rolling hills and a horizon punctuated by rows of lonely cypress trees. You really should take the time to visit this beautiful area of Tuscany and get to experience some of its’ wonderful artisan foods and wines at their source. The area is best known for the wonderful Pecorino di Pienza, made exclusively in and around the town of Pienza which is situated close to the wine producing towns of Montalcino and Montepulciano, home to the Tuscan classic wines.

Located in the gorgeous Val d’Orcia (a hilly region renowned for its hiking), Pienza itself is such a gem, it’s been named a World Heritage Site by UNESCO and is known as the “ideal city of the Renaissance”. Pope Pius II was born here, and after becoming pope, in 1458, he had the town completely rebuilt as an ideal Renaissance town.

Pitigliano: one of Tuscany’s “tufa towns”

town of pitigliano is one of the Beautiful Towns and Villages to Visit in Tuscany

Built into tufa cliffs high in the sky, the village looks like it’s actually hovering above you as you approach. Tiny and tranquil, the town doesn’t boast just spectacular views. Known as “Little Jerusalem”, you can learn more about the town’s Jewish history in the Jewish Museum of Culture, visit the old Jewish quarter, synagogue, and sample some local Jewish delicacies, “Sfratti”. These are stick-shaped biscuits filled with ground walnuts, honey, nutmeg, orange peel and wrapped in dough. They were apparently invented by the Jewish community as a result of police hitting them with sticks to force them into the ghetto. You should also be sure to visit the underground tunnels and caves dug into the tufa beneath the city. This labyrinth of passages and rooms has been in use since Etruscan times. Ask at the tourist office for details on when they are open to the public.

Siena: the multi-faceted city of Italy

town of Siena is one of the Beautiful Towns and Villages to Visit in Tuscany

When it comes to impressive cities in Tuscany, Siena is a must-see. This historic spot is home to one of Europe’s most magnificent Gothic cathedrals and is lined with narrow medieval streets, which fan out from the scallop shell-shaped main square, Piazza del Campo. Distinguished as the heart of Siena since the 1300’s, this expansive piazza is the place to go to get a true feel for the city’s spirit and enduring traditions.

Volterra: the city of Alabaster

town of Volterra is one of the Beautiful Towns and Villages to Visit in Tuscany

Although Volterra is becoming increasingly well-known, partly because of its role in Stephanie Meyer’s Twilight series,  this small town remains unspoilt. Volterra, with its medieval, winding streets and gorgeous views from its hilltop perch, dates back to an 8th century BCE Etruscan settlement; big parts of the defensive wall they built in the 4th century BCE are still standing, as is the 3rd century BCE gate into the city! But that’s not all for the ancient side of Volterra. Here, too, are remains of an ancient Roman amphitheater and bathhouse, as well as the renowned Museo Etrusco Guarnacci, boasting numerous Etruscan finds from the area.

Stroll down the historical center, step back in time and enjoy the timeless atmosphere that surrounds the town: taste its typical products and visit the handicraft workshops, where you’ll find many ideas for souvenirs from Tuscany, especially alabaster hand-made objects, which Volterra is famous worldwide for.

Pisa: much more than just the leaning tower

town of Pisa is one of the Beautiful Towns and Villages to Visit in Tuscany

One of Pisa’s more famous sights. Yes, Pisa’s got the Leaning Tower — but that’s not the only reason to go. The city, a half-hour’s drive southwest of Lucca, reached the height of its dominance in the 11th to 13th centuries. Thanks to the stunning churches, palaces, streets and squares of the era, Pisa still feels like a medieval powerhouse today. Come on the last Sunday of June to see the Gioco del Ponte, a series of battles staged in medieval costume every year since at least the 16th century. And, okay, the Leaning Tower is pretty cool, too. My tip: Come in the evening, as the sun’s just setting and after the tour buses have gone, and you’ll have the tower almost to yourself.

Montepulciano: the illustrious Vino Nobile

Montepulciano is one of the Beautiful Towns and Villages to Visit in Tuscany

Located a stone’s throw from Siena, Montepulciano is a feast for the senses. A wine-lover? Add this to the list. Not a wine-lover? After visiting, you will be. The city, full of elegant Renaissance palaces, ancient churches, charming squares and hidden corners, boasts vast panoramas all over the wonderful Val d’Orcia and Val di Chiana valleys that surround it. Montepulciano’s biggest claim to fame is its Vino Nobile di Montepulciano, a DOCG-rated wine that’s been consumed since the Middle Ages and is considered one of Italy’s best.

Montalcino: the famous Brunello di Montalcino wine

Montalcino is one of the Beautiful Towns and Villages to Visit in Tuscany

Smaller than Montepulciano (at some 5,000, its population is about a third of Montepulciano’s), Montalcino also is less touristy, even though its claim to fame is similar: It produces Brunello di Montalcino, often considered to be Italy’s best wine. Other than that, the town’s top boast is its Museo Civico e Diocesano d’Arte Sacra, with a wealth of medieval and Renaissance works surprising for the town’s size. There’s also a majestic 14th-century castle, still complete with a public park and walk along the ramparts.

Arezzo: a city made for Slow Travel

Arezzo is one of the Beautiful Towns and Villages to Visit in Tuscany

This town served as the backdrop for scenes from Life is Beautiful, and when you come here, you see why: The historic center of Arezzo is lovely and unspoiled. Its tranquility belies a powerful past that included being one of the 12 Etruscan capitals and then, in the Middle Ages, a wealthy independent republic. Now home to nearly 100,000, it’s a hot spot for art and culture lovers. Arezzo’s Church of San Francesco boasts a great cycle of frescoes by 15th-century master Piero della Francesca, Vasari’s frescoes in the Casa Vasari depict an artist’s life journey, and the Archaeological Museum displays numerous ancient finds. Perhaps it’s not surprising that Petrarch, the “father of humanism,” was born here in 1304.

Cortona: the “Under the Tuscan Sun” town

Cortona is one of the Beautiful Towns and Villages to Visit in Tuscany

In the southern Tuscan province of Arezzo, Cortona is a traditional walled Etruscan town. After Frances Mayes wrote about living here in Under the Tuscan Sun, Cortona, home to some 22,000, wound up indelibly on the tourist map, but no big buses, thank goodness! This town, remains well worth a stop with views that alone are breath taking, spreading from this dramatic hilltop town over the rolling countryside and Lake Trasimeno. Although the town is small, it’s packed with interesting sites to visit – such as the Diocesan Museum, where you’ll find a beautiful panel painting by Beato Angelico; and the MAEC, which holds fascinating artifacts found in surrounding archaeological sites. Beautiful churches, like the Santa Margherita Sanctuary are strewn around the town and well worth an explore. And there are lots of worthwhile sites, like the Museo dell’Accademia Etrusca, with ancient Etruscan gems from the nearby area.

Monteriggioni: one of the best-preserved medieval towns in Italy

Monterigionni is one of the Beautiful Towns and Villages to Visit in Tuscany

In medieval times this walled town with 14 towers was on the frontline of the battles between the rival city states of Florence and Siena, and it doesn’t take much imagination to journey back to the Middle Ages – some streets in Monteriggioni are virtually unchanged. The town, which makes an appearance in Dante’s Divine Comedy and the video game Assassin’s Creed, is promoted as the “gateway to the Middle Ages”, and is an ideal destination for history lovers. In June there’s even a medieval festival with duels, dances, and “medieval menus” at the local restaurants.

San Gimignano: the Manhattan of Tuscany

san gimignano is one of the Beautiful Towns and Villages to Visit in Tuscany

The most well-known Tuscan village on our list, this one may be bordering on town status, but San Gimignano started life in the 1150s as an Etruscan village. Today, the 14 towers of this medieval walled community provide an understandable draw for tourists seeking history, atmosphere and a taste of the rural Italy of old.

Known as the medieval Manhattan, San Gimignano is one of the most beautiful hill towns of Tuscany. Characterized by stone towers and narrow streets, it is surrounded by an expansive countryside filled with vineyards that produce the famous Vernaccia wine. The main square is Piazza del Duomo (home to the Cathedral) where you can also take in the sights of the Palazzo del Podestà, Palazzo del Popolo, the Loggia and various medieval towers. For a postcard-perfect view of the Tuscan landscape, climb the Torre Grossa, a tower housing masterworks by Benozzo Gozzoli, Filippino Lippi, Pinturicchio, and Lippo Memmi.

Collodi: birthplace of Pinocchio

collodi is one of the Beautiful Towns and Villages to Visit in Tuscany

The ancient Tuscan village of Collodi is well worth a visit. Most famous for being the birthplace of beloved children’s character, Pinocchio, this narrow fairytale village cascades down a hillside in central Tuscany between Florence and Pisa. This is a perfect Tuscan experience for storybook fans, and the dedicated park shouldn’t be missed. The Park of Pinocchio captures the imagination with bronze sculptures set among beautiful gardens, mazes and fountains. Collodi is also home to the villa and gardens of Garzoni, a beautiful example of Italian Renaissance design.

Fosdinovo: gateway to the historic Lunigiana region

fosdinovo malaspina is one of the Beautiful Towns and Villages to Visit in Tuscany

High in the steeper terrain of Northern Tuscany lies the enigmatic commune of Fosdinovo. It is dominated by the brooding Castello, which dates back to the 12th century, and now holds a museum and cultural center that you can visit. As well as walk around the remarkably well-preserved structure.

The full-circle view afforded from Fosdinovo’s hill-top location is remarkable. On clear days you can see all the way to the coast with the island beyond, and the spectacular vista of mountains that legend has it, inspired Dante’s Inferno. Charming narrow streets snake through the village, leading you to Piazza Garibaldi – an ideal square to watch the world go by and admire the setting.

Other towns that merit a visit:

  • Barga: The medieval town of Barga stands out for its spectacular setting, surrounded by chestnut forests and mountains in the valley of the Serchio River, close to Lucca, in the Garfagnana region. This hidden ancient village in Tuscany is a rabbit-warren of very narrow cobbled streets, tiny squares, and steep staircases. The Duomo in the center is ancient and beautiful, and provides panoramic views. Practically untouched by tourism, Barga is perfect for soaking up the true Tuscany, undisturbed by tourists. This will mean brushing up on your Italian before you go though!
  • Castiglion Fiorentino:  In Castiglion Fiorentino everything is either up or down. The peak is more like a pimple head and everything else is on the side. Located between Arezzo and Cortona, it is renowned for the Etruscan archeological site and for the nine arch loggia, overlooking the valley, constructed by Vasari in 1513.
  • Certaldo: The famous Tuscan writer “Boccaccio”, author of the Decameron and the Life of Dante was born here. Certaldo is a great place to enjoy Tuscan food especially in September/October, during the Boccaccesca Festival. In July, don’t miss “Mercantia”, an international street art festival.
  • Chiusi: Chiusi is a very small town but it boasts some extraordinary necropolis, the Porsenna’s Labyrinth and the National Archaeological Museum, which houses a real treasure of Etruscan finds and Greek and Roman pottery. The Etruscans of Chiusi made a particular kind of pottery called Bucchero ware that is very dark and imitates metal. The lake of Chiusi (located northeast of the city) is a perfect place for those who love nature and sports. Among the local products, do not forget to taste the olive oil DOP Terre di Siena and wine (Chianti Colli Senesi DOCG, IGT Toscana).
  • Sorano: Sorano is a town suspended in time, built on a high rock and this extremely picturesque position captivates all who visit it. Here the Etruscans build a majestic necropolis.
  • Suvereto: Suvereto is a small village, which dates back to the year 1000. Situated on the slopes of the hills overlooking the Costa degli Etruschi, it is a true jewel, rich in history and art, set in the green valley of the River Cornia.
  • Vinci: In Vinci, everything is about Leonardo: the native house, the church where he was baptized, the museum and the library dedicated to him, even the landscape, still intact, which Leonardo himself had contemplated daily.

If you’re feeling inspired to explore this historic and famously beautiful region of Italy, there’s surely no better way to soak up the atmosphere than with your own private driver and guide, to help you get the most out of your holiday. If you’re planning a trip contact me and I will be happy to chat. 

About Audrey De Monte

Born in New York City, to European native parents, and raised in Western Africa, I have studied, lived and worked on three continents (Africa, Europe and North America), and have traveled extensively throughout the world. Travel has shaped my life, who I am, and how I look at the world and travel continues to be my biggest teacher. Together with my native Italian husband, we speak 5 languages (French, Italian, German, Spanish and English of course). I have spent a lifetime in several countries in Western Europe, since early childhood, visiting family, friends, studying, living and working. I grew up with the local customs and traditions of these countries.