Updated December 6, 2023
If you're dreaming of a picture-perfect Italian getaway, look no further than Tuscany.
With its rolling hills, vibrant vineyards, and medieval villages full of charming cobblestone streets and beautiful architecture, Tuscany is a feast for the senses. No wonder it's been attracting visitors for generations!
While everyone flocks to Florence, Pisa, and Siena, the real magic of Tuscany is found in its hidden corners and small towns, where the locals still live life the way they have for generations. Each charming town has something unique to offer, whether it’s breathtaking views, incredible food and wine, or a fascinating history.
But with so many beautiful towns and villages to choose from, it can be overwhelming to decide which ones to visit. That's why I've put together a list of the best towns in Tuscany, each with its own unique personality and charm.
From the iconic hills of San Gimignano to the beautiful village of Montepulciano and the stunning countryside of Pienza, get ready to be transported to a world of beauty and romance.
Grab a glass of Chianti and get ready to discover the best-kept secrets of Tuscany. You'll fall in love with all that this region has to offer!
Buonconvento
Located halfway between Siena and Montalcino, the charming medieval village of Buonconvento is often overlooked by tourists, but it's definitely worth a visit.
Buonconvento has a long and fascinating history that dates back to Roman times. Its strategic location on the Via Francigena, the ancient pilgrim route from Canterbury to Rome, made it an important town for traders, pilgrims, and travelers.
In the Middle Ages, Buonconvento flourished under the rule of the powerful Sienese Republic, which left a rich legacy of art, architecture, and civic institutions. Today, Buonconvento is a peaceful and picturesque town that has preserved its medieval charm and character.
The medieval walls of Buonconvento are still intact and offer a fascinating glimpse into the town's past. Take a leisurely stroll along the ramparts and enjoy the panoramic views of the surrounding countryside. You can also visit the ancient gates and towers that once protected the town from invaders.
Located in the former church of Santa Maria degli Angeli, history lovers will enjoy the Val d'Arbia Museum of Sacred Art. The museum houses an impressive collection of religious objects, paintings, sculptures, and tapestries from the Middle Ages to the Baroque period.
Castellina in Chianti
A charming medieval village nestled in the heart of Tuscany, Castellina in Chianti is best known for its beautiful architecture, traditional cuisine, and of course, its world-famous Chianti wine.
With its narrow cobbled streets, stone houses, and lovely piazzas, Castellina in Chianti is a perfect destination for those looking to immerse themselves in the history and culture of Tuscany.
Take a stroll down the Via delle Volte, a picturesque street lined with arches and shops that has been the spine of the town for more than seven centuries. The town has many churches you can visit as well, including the Church of San Salvatore and the Church of San Martino.
Wander through the many charming shops and boutiques in town, where you'll find everything from handmade ceramics to beautiful textiles. While in town you'll also want to sample some of the local specialties, such as the famous Chianti wine, pecorino cheese, and cured meats.
There are numerous wineries in the area that offer tours and tastings, giving visitors a chance to sample some of the region's best wines. Additionally, there are plenty of restaurants in town that offer delicious local cuisine, often paired with a glass of Chianti.
If you enjoy spending time outdoors, Castellina in Chianti is also home to many hiking and cycling trails that provide stunning views of the surrounding hills and vineyards.
Cortona
Cortona used to be most famous for its Etruscan past, although today it’s better known as the location of Bramasole, the villa restored by author Frances Mayes and documented in her best-selling book Under the Tuscan Sun.
But Cortona is much more than Bramasole. Explore the well-preserved ancient fortifications, and wander the narrow streets and piazzas of the town, which are filled with shops, cafes, and restaurants.
One of the most iconic sights in Cortona is the Piazza della Repubblica, which offers stunning views of the surrounding hills and valleys. This is also where you’ll find the Palazzo Comunale, one of the town’s most well-known buildings.
If you’re interested in Etruscan history, the Museo dell’Accademia Etrusca (Etruscan Academy Museum) is a must-see. Founded in 1727, it is one of the oldest public museums in Europe and is dedicated to the study and preservation of Etruscan and Roman art and artifacts.
The museum has a large collection of Etruscan and Roman artifacts, including bronze and terracotta sculptures, vases, and pottery, as well as coins and jewelry. One of the most famous pieces in the collection is the Etruscan chandelier, which is made of bronze and features a sculpted image of a winged horse.
The museum is housed in the Palazzo Casali, a 13th-century building that was the former seat of the local government of Cortona. In addition to its impressive collection, the museum is well-known for its beautiful frescoes and ceiling paintings, including works by local artists like Pietro da Cortona.
Aside from its rich history and cultural offerings, Cortona is also famous for its delicious cuisine and fine wines. Indulge in a variety of local specialties at the town's many restaurants and trattorias. Wine lovers will appreciate the opportunity to sample the region's famous red wines, such as Vino Nobile di Montepulciano and Brunello di Montalcino.
Lucca
The medieval, fortified town of Lucca is best known for its perfectly preserved Renaissance walls. Built in the 16th century to protect the town from invaders, today you'll find a park on top of the walls that wraps around the city, providing beautiful views of the town and the surrounding countryside.
When you hear the words “town walls” you probably think of something tall, but narrow. Not the walls of Lucca!
They’re so wide that the park on top of them is part of the course for Lucca’s yearly marathon. For a fun couple of hours, take a walk along them or rent a bike and ride around them to see the town from all sides.
Lucca is also home to beautiful churches and cathedrals, like the Cathedral of San Martino and the Church of San Michele in Foro, which feature stunning art and architecture.
Aside from the walls, one of the most iconic sites of Lucca are its towers. There are about 25 surviving of the original 130 that were built. The most famous is the Torre Guinigi, which features a garden at the top filled with oak trees. You can climb the tower (it’s about 20 flights of stairs) and take in stunning views of Lucca and the surrounding hills from the top.
In the center of town you’ll find the Piazza dell'Anfiteatro, built on the ruins of the ancient Roman amphitheater. The oval shape of the piazza, as well as the curved façades of the surrounding buildings, still reflect the original structure of the amphitheater.
The piazza is a popular spot for locals and tourists alike to meet up, grab a drink or a bite to eat, and enjoy the lively atmosphere. The square is surrounded by restaurants, cafes, and shops, making it a great place to browse or relax during a trip to Lucca.
Lucca is also famous as the birthplace of world-renowned composer Giacomo Puccini. Puccini was born in Lucca in 1858 and lived there until he moved to Milan to study music. His family had been prominent in Lucca for centuries, and his father had served as a choir master in the local cathedral.
Throughout his life, Puccini maintained a strong connection to Lucca, often returning to visit his family and the town that he loved. Some of his most famous operas, like "Turandot," "La Bohème," and "Madame Butterfly," were inspired by his experiences in Lucca and the surrounding area.
Today you can visit several sites associated with Puccini, including his birthplace, now a museum dedicated to his life and work. The museum features artifacts and memorabilia, as well as recordings of his famous operas. Every summer, Lucca also hosts a Puccini festival, where you can enjoy outdoor concerts and performances of his famous operas.
Montalcino
The charming hilltop town of Montalcino is most famous for its Brunello di Montalcino wine, which is considered one of the finest wines in Italy.
Montalcino sits in a patchwork of rolling hills and valleys, dotted with vineyards, olive groves, and small medieval villages. The views from Montalcino are breathtaking, and a trip to Montalcino offers a chance to immerse yourself in the beauty of the Tuscan countryside.
The Tuscan town is filled with beautiful medieval architecture, charming narrow streets, and lively piazzas. Take in the city's most iconic sights, like the clock tower, offering stunning views of the surrounding countryside from the top, and the 14th-century Fortress of Montalcino.
If you're lucky enough to visit Montalcino in October, you can witness one of the town's most popular events – the Festival of the Thrush (Festa del Tordo). The festival has its roots in medieval festivities and hunting celebrations.
Each year in October, birds on migration, such as thrush, pass through the hills. During the Middle Ages, this was considered the prime hunting season. It was marked by lavish feasts and banquets that people from all social classes participated in, including noblemen, paupers, the wealthy, the poor, as well as the clergy and the laity.
The men's courage and skills were tested through typical medieval games, while women competed against each other in preparing banquets with the wild game brought back by their men from the woods, all in celebration of abundance and fertility.
Today the festival is celebrated with a procession through the city, with participants in medieval dress in the colors of the four quarters of the city dancing and singing through the streets. In the afternoon the historical procession makes its way towards the archery competition grounds, located under the bastions of the Fortress.
During the archery competition, archers representing each quarter of the city compete for the silver arrow, the symbol of victory. The victorious quarter gets to celebrate throughout the year before having a chance to defend their title at the next festival.
Montepulciano
Nestled in the rolling hills of Tuscany, Montepulciano is a charming medieval town known for its delicious wines and stunning architecture. The hilltop town gives visitors breathtaking views of the surrounding countryside.
Walk the narrow streets winding up the hill to the main square, Piazza Grande. The square is surrounded by impressive buildings, including the Palazzo Comunale, the town hall, and the Duomo, or Cathedral, of Santa Maria Assunta.
If you've visited florence the Palazzo Comunale will probably look familiar. It's a smaller replica of the Palazzo Vecchio in Florence. Montepulciano has been used as a stand-in for Florence in many movies and television shows, including Netflix's Medici series with Dustin Hoffman and Richard Madden.
You can easily spend all day exploring the narrow streets and alleys of Montepulciano. Many lead to hidden treasures, like San Biagio church, located just outside the town walls.
One of the unique features of Montepulciano is the network of caves and wine cellars that run underneath the town. These cellars have been used for centuries to age and store the town's famous Vino Nobile wine.
Take a tour of the cellars and learn about the winemaking process, from grape to bottle. It's a fascinating experience and a great way to sample some of the best wines Tuscany has to offer.
In addition to its wine, Montepulciano is also known for its delicious food. While you're there you'll want to indulge in local specialties like pici pasta with wild boar ragù and pecorino cheese. And of course, no visit to Montepulciano would be complete without trying the town's signature wine.
Monteriggioni
With its circular walls and watchtowers, the tiny, walled medieval village of Monteriggioni looks like something out of a fairy tale. The village is known for its rich history, having been built in the 13th century as a fortress to protect Siena from rival Florence.
Today this Tuscan village is a peaceful retreat for those looking to escape the hustle and bustle of modern life and immerse themselves in the tranquility of Tuscany.
One of the best things to do in Monteriggioni is simply to wander through the narrow streets and take in the medieval architecture. The town is small enough to explore on foot, and there are plenty of cozy cafes and restaurants where you can stop for a bite to eat.
For history buffs, there's a small museum inside the town walls where you can learn more about the history of Monteriggioni and the surrounding area. If you're feeling adventurous you can climb up and walk along the walls for stunning views of the russet roofs of the town and the Tuscan countryside beyond.
Pienza
Nestled in the rolling hills of southern Tuscany's Val d'Orcia, Pienza is a small but beautiful town that exudes charm and elegance.
Known as the "Ideal City" or "City of Pius," Pienza was rebuilt and redesigned in the 15th century by Pope Pius II. He wanted it to be a utopian town that embodied Renaissance ideals of beauty, balance, and harmony.
With its perfectly aligned streets and gorgeous architecture, Pienza has become a UNESCO World Heritage Site and a favorite destination for visitors to Tuscany. Enjoy the beautiful views of the surrounding countryside from the town's ramparts or explore the charming side streets and hidden corners of this picturesque town.
In the center of town you'll find the lovely Cathedral of Santa Maria Assunta, designed by Bernardo Rossellino and consecrated in 1462. The church was commissioned by Pope Pius II and intended to be an example of Renaissance architectural perfection.
Just across the street is the Palazzo Piccolomini, the family home of Pope Pius II, who was born Enea Silvio Piccolomini. This beautiful Renaissance palace was built in the 15th century by the Piccolomini family, who were one of the most powerful families in Tuscany at the time. It's an excellent example of Renaissance architecture, featuring beautiful details like the stone courtyard, the elegant loggia or covered porch, and the mullioned windows.
You can tour many rooms of the palace, which have been restored to their original Renaissance splendor. The palazzo also features a beautiful Italian garden, which offers stunning views of the surrounding countryside.
Pienza is also known for its excellent pecorino cheese, which is made using traditional methods from the milk of sheep that graze in the surrounding hills. The town's main street, Via del Casello, is lined with shops selling pecorino and other local products like honey and wine.
San Gimignano
San Gimignano will transport you back in time with its well-preserved medieval architecture. Located between Siena and Florence, the town was built in the 10th century as a way for the ruling families to show off their wealth and power.
Today, the small town is a UNESCO World Heritage Site, as it is one of the best-preserved examples of a medieval town in Italy. It's most famous for the 14 towers that have been dominating the skyline since the Middle Ages.
It's said that there were once 72 towers in San Gimignano, sitting on top of the hill like a Medieval Manhattan. The 14 medieval towers towers that remain are still quite impressive.
Enjoy the charming shops and restaurants as you stroll down Via San Giovanni, where you can see some of the town's most beautiful towers.
As you walk you may come across the Via Francigena, an ancient route that was once used by pilgrims traveling from Canterbury, England to Rome. The trail runs through San Gimignano's picturesque countryside, past vineyards, olive groves, and wheat fields, and offers views of the surrounding hills.
Stop in at the Cathedral of Santa Maria Assunta, where you can admire its beautiful frescoes. These frescoes tell the stories of the Old and New Testament, allowing even the illiterate to read them through pictures.
If you'd like to see the town from above, make sure to climb the Torre Grossa, the tallest tower in San Gimignano. The Museo Civico, which is housed in the beautiful Palazzo Comunale, showcases a variety of medieval and Renaissance art and is also worth a visit.
Volterra
The hilltop town of Volterra is best known for its rich history and culture, which dates back to Etruscan times. Its well-preserved ancient ruins, including the Etruscan Arch and the Porta all'Arco, are worth taking some time to explore.
Volterra’s Roman Theater dates back to the 1st century BCE and can still be seen today. The theater was built into the side of a hill and would have seated up to 3,000 people. You can explore the remains of the theater and imagine what it would have been like to attend a performance in ancient times.
The town is also home to stunning medieval and Renaissance architecture, like the Palazzo dei Priori, a medieval palace that was once the seat of government, and the Cathedral of Santa Maria Assunta.
Volterra is known for its alabaster production, which dates back to the Etruscan civilization, around the 7th century BCE. The Romans also exploited the vast deposits of alabaster in the area for their architectural and decorative works.
During the Middle Ages, the local artisans developed a unique style of carving and sculpting the stone, giving rise to the Volterran School of Alabaster.
Today, Volterra continues to be a center for alabaster production and is home to numerous shops, workshops, and factories dedicated to working with the stone. The town also hosts an annual alabaster fair, showcasing the works of local artisans and drawing visitors from all over the world.
The alabaster of Volterra is highly sought after for its quality, beauty, and uniqueness, and you can attend demonstrations to learn how the beautiful stone is carved and shaped.
The bottom line: The best towns in Tuscany
Tuscany is blessed with breathtaking towns and beautiful villages that offer a glimpse into Italy's rich cultural heritage. From the medieval charm of San Gimignano to the hilltop beauty of Cortona, the region is a treasure trove of fascinating destinations.
Whether you're interested in history, culture, art, or simply want to savor the delicious local cuisine and wines, Tuscany has something for everyone. With its rolling hills, lush vineyards, and picturesque countryside, Tuscany is the perfect destination for a romantic getaway, a family vacation, or a solo adventure.
So why not plan a trip to Tuscany and experience the charm and beauty of these remarkable towns and villages for yourself?
With so many fantastic places to stay, delicious food to enjoy, and exciting things to see and do, Tuscany is sure to capture your heart and leave you with unforgettable memories that will last a lifetime.
Like this post? Check out our posts on our favorite towns and villages in England and the prettiest towns in Provence, France.