The Best Places to Visit in Tuscany: From Florence to Chianti Hills

Tuscany is one of the most iconic postcards of Italy. The beauty of art cities like Florence, Pisa, and Siena, the charm of medieval villages like San Gimignano, the hills lined with vineyards and olive groves, the ancient thermal baths, and farmhouses immersed in greenery make this region the ideal destination for all types of travelers.

Rent a car or join a tour to discover the beauty of Tuscany, rich in history, art, and nature. Here are our recommendations for the most beautiful places to visit in Tuscany.

Florence: Elegant Charm and Ancient History

The first place to see in Tuscany is undoubtedly Florence. The capital of Tuscany was a major medieval center, the cradle of the Renaissance, and the capital of the Grand Duchy of Tuscany, led by the Medici and Lorena families. It was also the capital of the Kingdom of Italy from 1865 to 1871.

Today, its prestigious history is reflected in magnificent palaces, splendid galleries, and richly decorated churches in the historic center, a UNESCO World Heritage site. Admire Piazza della Signoria, Palazzo Vecchio, the Uffizi Gallery, which houses the world's largest collection of Italian and Florentine art, Palazzo Pitti, and the wonderful Boboli Gardens.

Then visit the Basilica of Santa Croce, the Basilica of Santa Maria Novella, and the Basilica of Santa Maria del Carmine. Most importantly, don't miss the majestic Duomo with Brunelleschi's immense dome. Climb to the top for a bird’s-eye view of Florence among its domes and red rooftops.

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Near Florence: Fiesole and the Sammezzano Castle

Did you know that just a short distance from Florence there’s a castle in perfect Moorish style? It’s the Sammezzano Castle, an architectural marvel with 365 rooms, one for each day of the year! But it is only open to visitors on rare occasions with guided tours.

Fans of archaeology should not miss Fiesole, an important Etruscan city just 10 km from Florence. You can see Etruscan and Roman remains, thermal baths, an amphitheater, and a magnificent view of Florence from atop the hill.

Siena: The Embodiment of a Medieval City

The UNESCO-listed historic center of Siena is described as the absolute embodiment of a medieval city. You only need one day to discover this small city with splendid Gothic architecture, where time seems to stand still.

Start from Piazza del Campo, the unique shell-shaped red square divided into nine sections, surrounded by noble palaces, and host to the city’s most important celebrations, including the famous Palio di Siena.

Marvel at the majestic Palazzo Pubblico, which houses the Civic Museum with famous frescoes by Ambrogio Lorenzetti, and Fonte Gaia, the most beautiful of Siena's fountains. For a panoramic view of Siena, climb the Torre del Mangia.

Continue to the Siena Cathedral with its opulent façade, and note the Piccolomini Library, frescoed by Pinturicchio, in the left aisle. Then proceed to the Siena Cathedral Museum, the Baptistery, and the National Gallery.

THE BEST TOURS AND ACTIVITIES TO VISIT SIENA

The Hills of Siena: Montalcino and San Quirico

Leaving Siena, you'll find yourself in hills dotted with charming villages and vast vineyards. Stop in Montalcino, the town that produces Brunello, one of Tuscany’s most famous wines. Just a few kilometers from Montalcino is San Quirico, a great stop for food and wine lovers, offering breathtaking views of the Val d’Orcia.

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Pisa: The Ancient Maritime Republic

The ancient maritime republic of Pisa centers around the Piazza dei Miracoli, considered one of the most beautiful squares in the world. Its green lawns are home to major landmarks like the cathedral, the baptistery, and the famous Leaning Tower.

The square, bustling with people at all hours, is where tourists take photos attempting to "straighten" the tower! You’ll also find many students here, as Pisa is home to three of Italy's most important universities: the University of Pisa, the Scuola Normale Superiore, and the Sant'Anna School of Advanced Studies. Then take a stroll through the city center, among narrow streets and buildings reflected in the Arno River.

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San Gimignano: One of Tuscany's Most Beautiful Villages

The historic center of San Gimignano, a UNESCO World Heritage site, stands on a hill in Val d’Elsa with its 14 medieval towers. Originally an Etruscan village named after the bishop of Modena, San Gimignano became a town in 1199 and flourished thanks to its location on the Via Francigena.

Today, San Gimignano is one of Tuscany’s most beautiful villages and a prime example of a 14th-century town, with medieval streets and a fairytale-like rural atmosphere.

Then visit the Town Hall with the Dante Room, the Collegiate Church—a Romanesque cathedral where scenes from Franco Zeffirelli's 1999 film Tea with Mussolini were filmed—as well as the churches of Sant’Agostino and San Lorenzo in Ponte. End your tour at the Rocca di Montestaffoli, a fortress with splendid valley views, hosting the Vernaccia di San Gimignano Wine Experience.

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Montepulciano: From Piazza Grande to Piazza Savonarola

An enchanting medieval village between Valdichiana and Val d’Orcia, Montepulciano has a long history dating back to its foundation by the Etruscans in the 4th century B.C. Start in Piazza Grande, the highest point of the village, and explore its historic center among narrow streets and Renaissance palaces.

Visit the Duomo, the Church of San Biagio, Palazzo Ricci, and its loggia with views of the surrounding countryside. Don’t miss the Town Hall, with its tower offering a stunning panoramic view.

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The Thermal Baths: Saturnia, Bagno Vignoni, Chianciano, and Montecatini

The most famous thermal baths in Tuscany are in Saturnia, where a hot spring flows at a constant temperature of 37.5 degrees Celsius. You can enjoy a relaxing bath in a luxurious hotel in Saturnia or at the free thermal baths.

Other renowned thermal sites in Tuscany include Bagno Vignoni, with its main square occupied by a large medieval basin, Chianciano’s conveniently located thermal baths, and Montecatini Terme near Pistoia, offering a relaxing setting with thermal waters and elegant architecture.

The Chianti Hills: Greve and Montefioralle

In the hilly region between Florence and Siena, you’ll find a charming landscape of dense forests, medieval villages, romantic castles, beautiful farmhouses, and vast vineyards. This is the heart of Tuscany, where the famous Chianti wine is produced.

Stop in the medieval village of Greve to taste this ancient wine before heading to Montefioralle, a fortified village full of charm. At the southwestern edge of Chianti, you’ll find Monteriggioni, a delightful 13th-century village that comes alive in July with a lively medieval festival.

THE BEST GUIDED TOURS TO EXPLORE THE CHIANTI HILLS

Cultural Tuscany: Following in the Footsteps of Dante, Boccaccio, and Leonardo da Vinci

If you’re tracing the footsteps of great writers, poets, and intellectuals born in Tuscany, begin in Florence. In the birthplace of the “supreme poet,” you can visit the Dante Alighieri House Museum, then continue to Certaldo, the hometown of another great master of the 14th century, Boccaccio.

His house is not the only attraction in this charming village on the Florentine hills. A few kilometers from Florence, Vinci is another famous village as it is the birthplace of Leonardo, a man of universal genius from the Renaissance. His house is worth a visit if you want to learn more about his life, works, and inventions that made Leonardo da Vinci one of humanity’s greatest minds.

Livorno: From the Beaches of the Tuscan Coast to the Historic Center

The third-largest city in Tuscany is a port city with ancient history and a cosmopolitan atmosphere. Declared a free port in the 17th century, Livorno attracted merchants from around the world who brought new customs, traditions, and ways of life to Tuscany.

Today, Livorno is a multicultural city famous for its excellent seafood.

Overlooking the Ligurian Sea, Livorno is a splendid destination to enjoy the beaches of the Tuscan coast, as well as its historic center, crossed by Venetian-style canals between elegant early 20th-century buildings.

• Don’t miss Piazza della Repubblica and Terrazza Mascagni, a sophisticated terrace facing the Tyrrhenian Sea. Visit the aquarium if you have children with you.

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The Most Beautiful Beaches in Tuscany

The Tuscan coast is very diverse. From secluded coves to equipped beaches, you just need to choose the one that suits you best.

• Along the so-called Etruscan Coast, in the province of Livorno, you’ll find the golden beaches of Baratti and San Vincenzo.
• In Versilia, in the province of Lucca, the sandy coast is famous for the lively beaches of Forte dei Marmi and Viareggio.
• In the province of Pisa, you’ll find free and tranquil beaches, more suited for families, such as those in Tirrenia.
• The most beautiful, however, is the Monte Argentario coast, where you’ll find secluded coves like Cacciarella, Cala del Gesso, and Cala Grande.
• Cala Violina is ideal for its white sand and crystal-clear sea. Alternatively, take a ferry to Elba Island to relax on scenic beaches like Sansone Beach.

Other Must-See Places in Tuscany

There are two other hidden gems in Tuscany we highly recommend:

The Tarot Garden

In the province of Grosseto, near Capalbio and the beaches, there’s the Tarot Garden, a one-of-a-kind garden adorned with sculptures by Niki de Saint Phalle that will immerse you in a dreamlike world of vibrant colors and shapes.

Sorano, Tuscany's Matera

Tuscany also has its own "Matera". It’s called Sorano, an ancient Etruscan town carved into tuff rock.

Now, tell us your favorite places in Tuscany. Share them in a comment!