Tuscany is one of the most captivating regions in Italy, where art, history, culture and breathtaking landscapes come together in a perfect blend. Each city in this region has its own unique charm, with a rich artistic and architectural heritage that dates back centuries.
If you’re planning a trip to Tuscany, these are the 10 cities you absolutely cannot miss.
1. Florence
Florence, the capital of Tuscany, is undoubtedly one of the most beautiful and famous cities in the world. As the cradle of the Renaissance, Florence is an open-air museum, rich in art and architectural masterpieces. Here you can visit the Uffizi Gallery, which houses works by artists such as Botticelli, Michelangelo and Leonardo da Vinci, stroll along the Ponte Vecchio or admire the majestic Cathedral of Santa Maria del Fiore with its dome designed by Brunelleschi. Florence is a vibrant city where art blends with fashion, cuisine and Italian culture.
2. Siena
Siena is famous for its perfectly preserved medieval historic center, which has been declared a UNESCO World Heritage Site. The heart of the city is Piazza del Campo, one of the most beautiful squares in Italy, where the famous Palio horse race takes place every year, a historic competition between the city’s districts. Siena also offers the splendid Gothic Cathedral, the Duomo of Siena, which houses works by Donatello, Michelangelo and Pisano. Walking through the streets of Siena feels like stepping back in time.
3. Pisa
Pisa is known worldwide for its Leaning Tower, one of Italy’s most iconic landmarks, but the city has much more to offer. The Piazza dei Miracoli, where the tower is located, also hosts the Cathedral, the Baptistery and the Camposanto, a monumental complex of extraordinary beauty. Pisa, once a powerful maritime republic, also has a lively university atmosphere, with many cafes and venues where you can experience the daily life of the city.
4. Lucca
Lucca is a charming city famous for its imposing Renaissance walls that enclose the historic center. The walls, now transformed into a pedestrian park, offer a pleasant walk with views of the city. Inside the walls, you’ll find splendid medieval churches, such as the Duomo of San Martino and the Basilica of San Frediano, as well as charming squares like Piazza dell’Anfiteatro.
Lucca is also the birthplace of the famous composer Giacomo Puccini.
5. San Gimignano
San Gimignano, known as the “Manhattan of the Middle Ages,” is famous for its towers that dominate the city’s skyline. Once, the richest families in the city built these towers as symbols of power. Today, 14 of the original 72 towers remain, creating a unique landscape.
The historic center of San Gimignano, a UNESCO World Heritage Site, is a medieval gem, with cobbled streets, historic palaces, and churches rich in frescoes.
Don’t miss a tasting of the famous Vernaccia di San Gimignano wine.
6. Arezzo
Arezzo is one of Tuscany’s cities richest in history and art. Piazza Grande, with its distinctive slope, is one of the city’s most charming spots and hosts the Giostra del Saracino every year, an ancient knightly tournament.
Arezzo is also famous for the Basilica of San Francesco, which houses the fresco cycle “The Legend of the True Cross” by Piero della Francesca, one of the masterpieces of the Italian Renaissance.
Walking through Arezzo’s streets means immersing yourself in a peaceful, history-rich atmosphere.
7. Pienza
Pienza, located in the heart of the Val d’Orcia, is a Renaissance jewel commissioned by Pope Pius II as the “ideal city.” The historic center, a UNESCO World Heritage Site, is a perfect example of Renaissance urban planning, with its Cathedral and the Piccolomini Palace dominating the main square.
Pienza is also famous for its production of pecorino, one of Italy’s finest cheeses. Its location offers breathtaking views of the surrounding hills, making it a must-visit for photography and nature lovers.
8. Montepulciano
Montepulciano is a picturesque hill town famous for its wines, especially the Vino Nobile di Montepulciano. The historic center, with its narrow and steep streets, is rich in Renaissance palaces and offers spectacular views of the surrounding countryside. Piazza Grande, the heart of the city, houses the Cathedral and the Palazzo Comunale, from which you can enjoy a panoramic view of the Val d’Orcia. Montepulciano is also known for its underground cellars, some of which date back to the Middle Ages and can be visited.
9. Cortona
Cortona is one of the oldest cities in Tuscany, with origins that trace back to the Etruscans. Perched on a hill overlooking the Val di Chiana, it offers spectacular views of Lake Trasimeno and the surrounding hills. Cortona is famous for its narrow alleys and ancient walls, as well as its museums, such as the MAEC (Museum of the Etruscan Academy), which houses an extraordinary collection of Etruscan artifacts.
The city gained additional fame thanks to the book Under the Tuscan Sun, which attracted many visitors from around the world.
10. Volterra
Volterra is an ancient and fascinating city with a history dating back to the Etruscans.
Famous for its alabaster craftsmanship, Volterra still preserves many traces of its Etruscan and Roman past, such as the imposing Porta all’Arco and the Roman Theater. The historic center is characterized by cobbled streets, medieval palaces, and a magnificent Cathedral.
Volterra also offers panoramic views of the surrounding hills and an authentic, tranquil atmosphere, far from the more crowded tourist destinations.
Tuscany is a region full of charming cities, each with its own history, character, and unique landscapes. Whether you are an art lover, a history enthusiast, or simply a traveler seeking beauty and authenticity, these ten cities will surprise and enchant you.
