Tuscany is not only one of Italy’s most picturesque and beloved regions, but it also embodies everything you dream of when thinking of this incredible country. From breathtaking landscapes of hills, mountains, seas, and valleys to open-air museums, rich cultural heritage, and exquisite cuisine, Tuscany offers an unforgettable experience. With several years of experience living and exploring this remarkable region, I recommend four of the most beautiful towns in Tuscany for you to enjoy firsthand.

Top Beautiful Towns in Tuscany

Certaldo

Nestled in the Val d’Elsa in the province of Florence, Certaldo is one of Tuscany’s most charming villages. Perched on a hilltop, Certaldo preserves its medieval architecture, evident in its narrow cobblestone streets and historic buildings. This small town, known for its beauty, is furthermore famous as the birthplace of Giovanni Boccaccio, the renowned author of “The Decameron.”

Things to Do in Certaldo

• Ride the Funicular: Take the funicular to the historic center for a panoramic view of the town and valley. Operating since 1999, it offers a unique way to access the city, along with walking paths and permitted drives.
• Visit Boccaccio’s House-Museum: Explore the museum dedicated to Giovanni Boccaccio, featuring a library with copies of “The Decameron” and personal items of the poet.
• Explore Palazzo Pretorio: Located at the end of the main street, this landmark features a facade adorned with family symbols from Certaldo’s past rulers.
• Taste Local Flavors: Enjoy Certaldo’s unique round red onions in jams, onion soup, and even onion cream ice cream at local eateries like Enoteca Boccaccio Di Casini Andrea, Osteria Da Chichibio, and Gelateria di Bracali Patrizia.

 

San Gimignano

Known as the “Manhattan of the Middle Ages,” San Gimignano boasts medieval towers that symbolize historical power. This UNESCO World Heritage Site, known for preserving medieval architecture, art, and traditions, is a top Tuscan destination.

Things to Do in San Gimignano

• Explore the Historic Center: Wander through San Gimignano’s historic center to admire its beautiful architecture and rich history.
• Visit the Duomo: Famous for stunning frescoes by artists like Lippo and Federico Memmi, the Collegiata Santa Maria Assunta awaits.
• Climb Torre Grossa: For a panoramic view of the city and the surrounding valley, climb the tallest tower in San Gimignano.
• Relax at Piazza della Cisterna: This triangular square, famed for its medieval cistern, provides access to intriguing sites like Vicolo dell’Oro.
• Savor Local Gastronomy: Try San Gimignano’s saffron and Vernaccia white wine at local spots like Le Vecchie Mura and Gelateria Dondoli, awarded the world’s best gelateria multiple times.

Monteriggioni

Monteriggioni is a charming medieval village surrounded by well-preserved walls, built by Siena to defend against the Florentines. Despite its small size, Monteriggioni offers a rich experience of Tuscan culture and cuisine.

Things to Do in Monteriggioni

• Walk the Village Walls: Enjoy stunning views of the countryside and the village from the medieval walls.
• Visit Santa Maria Assunta: This small church in the main square, dating back to the town’s founding, holds historical significance.
• Dine at Ristorante Da Remo: Enjoy traditional Tuscan dishes, including Siena’s specialties like fresh handmade pici al caccio e peppe, in a cozy atmosphere.

Pienza

Located in the Val d’Orcia, Pienza is famous for its breathtaking landscapes and is often called the “city of light.” Redesigned by Pope Pius II, this town offers a perfect blend of natural beauty and historical significance.

Things to Do in Pienza

• Stroll the Romantic Streets: Wander through Via del Bacio (Street of the Kiss) and Via dell’Amore (Street of Love), leading to terraces with stunning Val d’Orcia views.
• Visit Palazzo Piccolomini: Once the residence of Pope Pius II, this 15th-century palace boasts a garden designed for perfect Val d’Orcia views.
• Taste Pecorino Cheese: Pienza’s pecorino cheese is a local delicacy you can find in many of the town’s cheese shops.
• Explore the Cathedral: This Renaissance-style cathedral, built on the remains of a Romanesque church, showcases architectural and historical marvels.

Each Tuscan town offers unique beauty, rich history, and cultural significance, enhancing Tuscany’s reputation as a top Italian destination. Discover and enjoy the charm of Tuscany through these stunning towns.