The 10 Most Beautiful Villages in Tuscany

If you're dreaming of a getaway that combines breathtaking landscapes, rich history, and charming villages, the Tuscan countryside is your ideal destination. In this article, we will explore the top ten most beautiful towns in Tuscany, each one a gem waiting to be discovered on your next Italian adventure.

Tuscany is a region that captures the heart of every traveler. With its rolling hills, historic architecture, and world-renowned culinary delights, it’s no wonder this area is on many people's bucket lists. Beyond the famed cities like Florence and Pisa, Tuscany is dotted with quaint villages that embody the essence of Italian culture and history. Prepare your senses for a journey through the rustic beauty and culinary delights of these enchanting towns.

Discover the 10 most beautiful towns in Tuscany

Ready to explore the hidden treasures of Tuscany? Here’s our curated list of the ten most beautiful towns that you simply cannot miss:

1. San Gimignano: The Medieval Manhattan

Famous for its stunning towers, San Gimignano has earned the nickname "The Manhattan of the Middle Ages." This picturesque town, with its medieval skyline, is a UNESCO World Heritage site.

While here, indulge in some of the country's best gelato at the renowned Gelateria Dondoli and wander through its charming cobblestone streets. As the sun sets, enjoy live guitar melodies in the main square while sipping a glass of local wine. Did you know? Only 14 of the original 72 towers remain, a testament to the town's rich history and the display of power by local nobility.

2. Montefioralle: A Hidden Gem

Just a short drive from San Gimignano lies Montefioralle, a tiny village brimming with charm. Nestled in the Chianti region, it offers a serene escape from the hustle and bustle.

Get lost in its narrow vicoli, colorful flowerpots, and medieval castle. This small village is like stepping back in time, where every corner tells a story.

3. Volterra: The Etruscan Marvel

Known for its Etruscan origins, Volterra has a unique charm that transcends time. With its ancient walls and winding streets, it offers breathtaking views and a glimpse into history.

Visit significant sites such as the Piazza dei Priori, the octagonal baptistery, and the Roman theater. The panoramic views from the Piazza dei Santi Martiri della Libertà are unforgettable, making this town a photographer's paradise.

4. Montepulciano: A Taste of Tuscany

Picture rolling hills, lush vineyards, and delectable food. Montepulciano encapsulates the Tuscan dream. This hilltop town is famous for its Vino Nobile di Montepulciano, a red wine that perfectly complements its culinary scene.

Explore landmarks like the Plaza Grande, the Town Hall, and the beautiful churches. Don’t forget to visit a local winery for a tasting—cheers to that!

5. Pienza: The Ideal City

Pienza is a stunning example of Renaissance architecture, designed by Pope Pius II to be the "ideal city." Its well-planned layout and beautiful buildings have earned it a place on the UNESCO World Heritage list.

As you stroll through its streets, you’ll encounter magnificent palaces, the Catedral, and the lovely central square. Be sure to try the local cacio di Pienza, a delicious sheep's milk cheese that will leave your taste buds dancing.

6. Bagno Vignoni: A Unique Thermal Town

What sets Bagno Vignoni apart is its thermal waters, once favored by Roman aristocrats for their healing properties. While swimming is no longer allowed, the charming village is worth a visit for its stunning thermal square, Piazza delle Sorgenti.

For those who love thermal baths, don’t miss the Saturnia Springs, located just a short drive away. They are among the most beautiful thermal baths in the world.

7. Castiglione d’Orcia: A Fortress in the Hills

Perched atop a hill, Castiglione d’Orcia is known for its impressive fortress, Rocca di Tentennano, which dates back to the 11th century. The views of the surrounding countryside from here are simply breathtaking.

The area also boasts natural hot springs, such as the Bagni San Filippo, known for their unique carbonated formations. The best part? They are free to access!

8. Montalcino: The Home of Brunello

Another medieval town, Montalcino is often recognized as the birthplace of Brunello di Montalcino, one of Italy’s finest wines. Its cobblestone streets and historic buildings exude a timeless charm.

Visit the impressive fortress, the Duomo, and the Palazzo dei Priori. Make sure to stop by a local vineyard to savor the rich flavors of the Brunello wine.

9. Pitigliano: The Little Jerusalem

Enclosed within towering cliffs, Pitigliano is renowned for its dramatic setting and ancient architecture. The village is often referred to as "Little Jerusalem" due to its historic Jewish community.

Wander through its labyrinthine streets and visit the ancient synagogue and ghetto, which reflect the town's rich cultural tapestry. The stunning views and unique architecture make Pitigliano a must-visit destination.

10. Sorano: The Hidden Treasure

Last but not least is Sorano, a lesser-known gem that offers an authentic Tuscan experience. This charming town is often overshadowed by its neighbors but boasts an enchanting atmosphere of tranquillity.

Explore the winding streets, discover ancient Etruscan paths, and experience the local hospitality. The hotel Della Fortezza offers breathtaking views and a warm welcome, making it the perfect place to unwind after a day of exploration.

Map of the Most Beautiful Towns in Tuscany

Here’s a map highlighting the locations of these enchanting Tuscan towns, guiding you as you plan your adventure:

How to Visit Tuscany

We recommend exploring these towns by car for the ultimate freedom and flexibility. A road trip through Tuscany is an unforgettable experience, allowing you to soak in the vast landscapes and hidden treasures at your own pace.

• Chianti + San Gimignano
• Siena + Val D’Orcia
• Val D’Orcia + Maremma
• Termas + Volterra + Pisa

Alternatively, if you prefer not to drive, various guided tours and excursions are available:

• Tour to Montalcino, Pienza, and Montepulciano from Florence
• Excursion to San Gimignano, Siena, and Chianti from Florence
• Tour to Siena, San Gimignano, Pisa, and a Chianti winery from Florence
• Enoturismo in Chianti from Florence
• Vespa Tour in Chianti from Florence
• Tour to Montalcino, Pienza, and Montepulciano from Siena

With so many stunning towns to explore, it’s easy to get lost in the beauty of Tuscany. These ten villages are just the tip of the iceberg when it comes to the wonders this region has to offer. What are your favorite towns in Tuscany? The adventure awaits!

Top attractions to see in Val d'Orcia Tuscany