The Best Towns in Tuscany to visit and explore

Let’s go on a trip through the dreamy towns of Tuscany. This region of Italy is a dream that fills both the imagination and the senses. Rich in both fine art and rural beauty, this exquisite and diverse region has something for everyone.

From the big cities bursting with Renaissance art and quaint villages frozen in time, to vineyards dotting the rolling hills and the best food in the world, a trip to Tuscany is something many people yearn for. How will you choose the best towns in Tuscany to visit on your trip to Italy?

Famous towns in Tuscany

Cosmopolitan in flavor, and famous for Renaissance art, these cities are among the best places to stay in Tuscany. They are small and have the amenities of a city, yet are well positioned so you can explore the rest of this diverse region.

Florence

Florence has captured the imagination of visitors over the centuries. The regional capital of Tuscany, its historic center was declared a UNESCO World Heritage Site in 1982. Florence’s rich artistic and architectural heritage inspired Travel + Leisure readers to recently rank it as the best city in Europe.

Many historians consider Florence to be the birthplace of the European Renaissance. During that time, Florence was home to such luminaries as Leonardo da Vinci, Michelangelo, and Botticelli. The art and architecture of this fabulous time remain at the heart and soul of this world-class city.

Florence remains world-renowned for its sophisticated culture and is home to many art galleries and museums, such as the Palazzo Pitti and the Uffizi Gallery. Here you can immerse yourself in the true spirit of the Renaissance, dine in style and shop for unique artisan goods. Or simply wander along the Arno admiring the beauty all around you.

Pisa

Thanks to the leaning tower, Pisa is one of the most popular places to visit in Tuscany. But, there is so much more to this fascinating city.

Many visitors simply make a beeline for the tower and miss the rest of the city. With more than 20 historic churches, medieval castles, and ancient bridges across the River Arno, there is much to explore in Pisa. The pretty old town dates to pre-Roman times, but most of the buildings you see today were built between the 9th and 16th centuries. You can also visit the Museo dell’ Opera del Duomo which has original sculptures by Nicola and Giovanni Pisano as well as other valuable works of art belonging to the cathedral.

At the northern end of the historic town center, you’ll find the famous Leaning Tower of Pisa. The monument is the bell tower of the cathedral and is just one of many works of art and architecture in the Piazza dei Miracoli. Pisa’s Cathedral was built in 1063, but construction on the bell tower did not begin until 1173.  Completed in 1372, it began to lean almost immediately, due to soft, unstable ground.

Lucca

Lucca is famous for the Renaissance-era walls that encircle the Old City. The walls were initially built for defense, but once the threats from neighboring Pisa and Florence abated, they were transformed into the Passeggiata delle Mura Urbane, a pedestrian promenade. The old town is also home to the Piazza dell’Anfiteatro, built on the site of an ancient Roman amphitheater.

There is so much to see and do in Lucca, including the Casa di Puccini, home of the renowned opera composer. In fact, a Puccini opera festival is held here every summer.

While in Lucca, be sure to visit not only the museums, but the palaces; these spectacular homes of the old aristocracy are sublime. The Villa Garzoni, for example, is famous for its water gardens, and the Pallazo Pfanner, also known for its gardens, now serves as a museum.

Siena

The historic city center of Siena has also been declared a World Heritage Site by UNESCO. It is one of the must-see places to visit in Tuscany, famous for its fine cuisine, medieval buildings, and museums. Siena is also famous for the Palio di Siena, a horse race held twice a year, featuring ten bareback riders dressed in Renaissance garb. The historic race has been held in some form since medieval times.

The Siena Cathedral, a 12th-century masterpiece of Italian Romanesque-Gothic architecture, is one place you must visit. The interior of the cathedral has a vast display of Renaissance paintings and sculptures. Siena is also home to many old patrician villas, some of which were designed by the 16th-century architect, Baldassarre Peruzzi. While Siena is brimming with art and architecture, simply wandering the old streets will transport you back in time to those golden years.

Wine towns of Tuscany

While the cities of Tuscany are masterpieces of both Medieval and Renaissance art and architecture, the wine towns hearken to a simpler life. Nestled in the rolling, romantic hills are old farmhouses, ancient ruins, and quaint country churches. There are also fabulous villas and castles, as nearly every noble Tuscan family had a country estate with expansive vineyards.

Let’s pay a visit to a few of the best wine towns in Tuscany.

Montepulciano

Perched high on a limestone ridge, Montepulciano is a Medieval and Renaissance hill town renowned for its cheese, pork, thick hand-rolled pasta, honey, and lentils, as well as its world-famous wine. Connoisseurs the world over consider Vino Nobile di Montepulciano among Italy’s best red wines.

Most of the restaurants and shops are along the main street, stretching for less than a mile from Porta Al Prato to the Piazza Grande. Likewise, many of the streets are car-free, making this quaint town easy to walk. While you’re in Montepulciano, pay a visit to the local cathedral, constructed between 1594 and 1680. This unassuming cathedral includes an artistic masterpiece, the Assumption of the Virgin by Taddeo di Bartolo completed in 1401.

Montalcino

The hill upon which Montalcino is perched has been settled since Etruscan times. The hilltop offers a stunning view of the Arbia, Asso, and Ombrone valleys, dotted with olive groves, vineyards, villages, and fields. It’s truly a step back into time.

The hill of Montalcino is covered by olive orchards and vineyards. This wine town is famous for its Brunello di Montalcino wine, made from the deep purple Sangiovese Grosso grapes. Brunello di Montalcino must be aged for 5 full years before it can be released. The town is also famous for its sweet white wine, Moscadello.

Greve

Situated in the Val di Greve, this Tuscan wine town is named after the small, fast-running river that flows through it. Greve is the main town in the Chianti wine district stretching between Florence and Siena.

The Chianti wine region not only grows the grapes that produce the world-famous Chianti wines, but extra virgin Tuscan olive oil is also a highly prized product. Truffle harvesting is also notable – both black and white truffles can be found around Greve.

Wild game is often found on local menus, including pigeon, rabbit, venison, and wild boar. Likewise, the region’s unique Cinta Senese pig produces pork products of superior quality. Be sure to visit the Macelleria Falorni, one of Italy’s oldest and most renowned butcher shops in Tuscany, right here in Greve.

San Gimignano

Known not only for its wine but the Town of Fine Towers is also famous for its medieval architecture. There are around a dozen tower houses and medieval walls, enclosing well-preserved examples of Romanesque and Gothic architecture. In fact, the historic center of San Gimignano is a UNESCO World Heritage Site.

The town is known to the culinary world for saffron, golden ham, and Vernaccia di San Gimignano, a white wine. This white wine is produced from the ancient Vernaccia grape, which grows on the rustic sandstone hills surrounding the town.

Hill towns of Tuscany

Originally built in ancient and medieval times for defense, today the hill towns of Tuscany serve as a refuge from the modern world. After experiencing the hustle and bustle of the region’s urban cities, the hill towns are a peaceful change of pace. With a rich diversity of scenery, historic architecture, and wineries, the Tuscan countryside is just the place to slow down and abandon the modern world.

Pienza

UNESCO declared Pienza a World Heritage Site in 1996 and 2004, the entire Val d’Orcia valley, was listed among UNESCO’s World Cultural Landscapes. Needless to say, this gorgeous place is steeped in history.

The small town of Pienza is an old Renaissance village with well-designed streets and squares. The Palazzo Piccolomini, Palazzo Vescovile, Palazzo Comunale, and the Cathedral are all attributed to Pope Pius II and feature gorgeous architecture and works of art. Be sure to visit the sublime Piccolomini gardens, which offer spectacular views over the Val d’Orcia.

Cortona

Cortona’s steep narrow streets and medieval architecture are situated on a hillside with an elevation of 2,000 feet. From the town’s lofty hilltop, you’ll get a spectacular view of the whole Valdichiana valley. These are the scenes that inspired Frances Mayes’ novel Under the Tuscan Sun. Likewise, from the Piazza Carbonaia is an exceptional view of Lake Trasimeno, where Hannibal ambushed the Roman army in 217 BC.

You can still see parts of the very ancient Etruscan city wall at the base of the present wall, which was built in medieval times. Go inside the Museo dell’Accademia Etrusca, on the Palazzo Casali to see displays from the ancient Etruscan, Roman, and Egyptian civilizations. The museum also displays art and artifacts from the town’s illustrious Medieval and Renaissance history.

Pitigliano

The quaint medieval hill town has long been known as Little Jerusalem, due to the presence of its Jewish community. For hundreds of years, Jews found a safe haven in Pitigliano, both from the 16th-century Counter-reformation persecutions and from the Nazis. The town is built on tufa stone from which tunnels and caves were carved to serve its citizens.

While today there are very few Jews left in Pitigliano, the synagogue, which was built in 1598 and outfitted with 17th and 18th-century furnishings, still sees services from time to time.

If you’re the type of person who loves exploring small laneways and winding stairways on the lookout for breathtaking views then you’ll no doubt be charmed by Pitigliano.

Arezzo

Described by Roman historian Livy as one of the Etruscan capitals, Arezzo was an important city in pre-Roman times. Arezzo has survived to the present day as a beautiful town filled with medieval, Renaissance, and Romanesque architecture.

Each year a medieval festival known as the Saracen Joust is held in the main square. Knights on horseback representing the town’s different neighborhoods take aim at a target attached to a representation of a Saracen king, scoring points for accuracy. During the festival, nearly everyone in town dresses in medieval costumes to cheer on their champions.

Don’t worry if you miss this festival, Arezzo host several food festivals and events throughout the year. And it’s famous for small bars where you can relax at aperitivo hour.

Volterra

Not far from Florence, Volterra is a walled mountaintop town with a history dating from before the 8th century BC. The town has a charming blend of architectural styles, with structures and buildings from the Etruscan, Roman, and Medieval periods. Simply wandering the winding cobbled streets is one of the highlights of visiting this pretty Tuscan town.

Among the sights in Volterra is the Roman Theatre of Volterra, dating from the 1st century BC, and the frescoes in the Church of San Francesco, which was built in the 13th century. Volterra is beautifully preserved, with its impressive ancient walls and fortress. It’s also well known as a destination to shop for artisan-made handicrafts of the region.

Monteriggioni

Monteriggioni is a picturesque and almost perfectly preserved medieval walled town in Tuscany. Built between 1213 and 1219, the town’s Piazza Roma is dominated by a simple Romanesque church, as well as many Renaissance homes once owned by the local gentry.

To the side of the main piazza, you’ll find small cobblestone streets, public gardens, and quaint small businesses. It’s a pleasant place to simply wander on a sunny, summer day much as the pilgrims on the Via Francigena pilgrim trail have done for centuries.

Which is your favorite of these most beautiful towns in Tuscany?

These gorgeous cities and towns are no doubt the best places in Tuscany to visit and, if you can, linger a while to soak them up. Just picture yourself sauntering down cobbled streets at dusk, looking for the perfect spot to enjoy aperitivo hour.

From local wine and culinary experiences to historic architecture and traditions that span centuries, these Tuscany towns have a way of finding a big place in your heart. I can’t choose a favorite, can you?

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