The 10 Most Beautiful Towns in Tuscany, Italy You Can’t Miss

Looking for the most beautiful towns in Tuscany? You’re in the right place!

Here’s a list of the top 10 towns in Tuscany that you won’t want to miss – each one personally explored and tested during my unforgettable journey through this magical region.

Tuscany isn’t just about Florence – it’s a region filled with stunning landscapes, world–famous vineyards, charming towns, and incredible food that will change how you think about Italian travel.

If you’re planning a trip, renting a car is a great way to explore at your own pace and discover some hidden gems along the way.

Trust me on this – some of my best memories came from those spontaneous stops between planned destinations.

Check out my guide to Tuscany’s most charming towns and start planning your unforgettable adventure. Have an amazing trip!

1. Greve in Chianti: One of the Most Beautiful Towns in Tuscany

The first stop to consider in Tuscany is the charming town of Greve in Chianti, located in the stunning province of Florence.

When I first arrived here, I immediately understood why this place captures every traveler’s heart.

Known for its scenic beauty, the town takes its name from the river flowing through it and the famous Chianti wine region it calls home.

But here’s what the guidebooks don’t tell you – the real magic happens when you slow down and let the town’s rhythm become yours.

The main charm of Greve in Chianti is Piazza Matteotti, a picturesque square surrounded by medieval buildings and a Franciscan monastery.

I spent an entire morning here, and here’s my advice: grab a seat at one of the square’s cozy cafes and enjoy a cup of delicious coffee.

It’s the perfect way to start a truly Italian day, and you’ll notice how locals greet each other – it’s like watching a beautiful daily ritual unfold.

2. Montefioralle

The next village to explore in Tuscany is Montefioralle, tucked away among lush olive groves and vineyards.

When I discovered this gem just a short distance from Greve in Chianti, I felt like I’d stumbled upon a secret that only locals knew.

Its charming, narrow streets are perfect for a relaxed stroll, and here’s something I learned the hard way – wear comfortable shoes!

The cobblestones are gorgeous but not exactly forgiving on your feet. The village is simply enchanting and offers stunning views that make it a must-visit spot.

Plan your visit to Montefioralle in March to catch the Festa di Fritelle, where you can sample a variety of local treats.

Since parking is limited, walking from Greve in Chianti is a great option – it’s a scenic stroll that takes about 30 minutes and honestly became one of my favorite parts of the entire trip.

3. Panzano in Chianti

Another must-visit spot in Tuscany is Panzano in Chianti, perched at nearly 500 meters (1,600 feet) above sea level. The drive up here is spectacular, but what awaits at the top is even better.

This charming town is famous for its annual Vino al Vino festival, held every third weekend in September, and the legendary butcher shop of Dario Cecchini, where you can indulge in the perfect bistecca alla fiorentina.

Let me tell you – I’ve never tasted steak like this anywhere else in the world.

Don’t miss the medieval castle, the oldest and tallest building in town, or the nearby church of San Leolino, which features stunning works by artists like Giovanni della Robbia and Raffaelino del Garbo.

4. Radda in Chianti

After exploring Panzano, it’s definitely worth heading further south to the medieval village of Radda in Chianti. This place stole my heart with its authentic atmosphere – no tourist traps, just genuine Italian charm.

This charming town captivates with its narrow streets and the delicious aromas wafting from the gardens of restaurants in the main square. I followed my nose here more than once, and it never led me wrong.

Make sure to set aside some time for lunch or dinner at La Bottega di Giovannino.

I highly recommend trying dishes like the classic ribollita bean soup, ricotta ravioli in aromatic sage sauce, mushroom gnocchi, and panna cotta with fresh fruits.

Everything tastes amazing, and a glass of red wine is the perfect way to complement these delicious flavors. The owner treated me like family from the moment I walked in.

5. Monteriggioni

Monteriggioni, sitting on a hill, is one of the most beautiful towns in Tuscany.

When I first saw its fortress walls rising from the landscape, I literally stopped the car and just stared–it looks like something from a fairy tale.

The town is famous for its impressive fortress, built in the early 13th century by the people of Siena, complete with fourteen towers.

It was designed to defend against attacks from Florence and Volterra, and amazingly, it stayed unconquered for hundreds of years!

You can explore the whole town in just a few minutes, but it’s worth sticking around a bit longer, especially to enjoy some ice cream at Gelateria La Bottega del Castello – trust me, after walking those ancient streets, you’ll have earned it.

Check out Piazza Roma, the main square, with the beautiful Romanesque church of Santa Maria Assunta and the well-preserved city walls.

You can even climb to platforms on the walls to take in stunning views of the area (a small fee to enter, but worth every euro).

The town’s beauty has made it a popular spot for movies, commercials, and video games. Even Dante mentioned Monteriggioni in his “Divine Comedy“, and it’s easy to see why with those gorgeous views!

6. Pienza

When visiting Tuscany, you absolutely can’t miss one of Europe’s most beautiful wine regions – the Val d’Orcia Valley. I spent three days here and could have easily stayed a week.

Stretching from the hills south of Siena to Monte Amiata, it’s famous for its stunning landscapes dotted with charming medieval towns. No wonder it’s on the UNESCO World Heritage List.

A highlight in this area is the lovely town of Pienza. Once a modest Tuscan village, Pienza was transformed into a vision of the “ideal Renaissance city” by Pope Pius II, who was born nearby.

Thanks to brilliant architects, you can admire 15th–century gems like the Duomo, Palazzo Comunale, and Palazzo Piccolomini, all offering incredible views of the valley.

Fun fact: the gardens of Palazzo Piccolomini were used in the 1960s to film the Oscar-winning Romeo and Juliet. Standing where that famous balcony scene was shot gave me chills!

To take in even more of the stunning landscapes, stroll along Via dell’Amore and the charming streets behind the cathedral.

In addition to the main attractions, make sure to visit the Romanesque church of Pieve di Corsignano just outside Pienza.

Since Pienza is famous for its sheep products, be sure to grab some pecorino cheese from one of the local shops.

There’s a wide range of flavors and ages, from a few months to several years, so you’ll definitely find one you love.

And when you’re in town, take time to enjoy lunch at Trattoria da Fiorella.

I recommend trying pecorino cheese with red radicchio (Italian chicory), and for the main dish, the handcrafted taglierini with duck in a delicate white sauce – it’s absolutely delicious and still makes my mouth water thinking about it!

7. Monticchiello

After exploring Pienza, it’s definitely worth heading to another charming village in the Val d’Orcia valley – the medieval hamlet of Monticchiello.

Along the way, make sure to stop at Photo Spot Toscana, where you can take in one of Tuscany’s most iconic landscapes: a winding avenue of cypress trees snaking through lush hills – perfect for capturing unforgettable photos.

I must have taken fifty pictures here, and every single one looked like a postcard.

While Monticchiello doesn’t have many attractions, it’s worth a quick visit for the breathtaking views and the historic church of Santi Leonardo e Cristoforo. Sometimes the smallest villages leave the biggest impressions.

8. Montepulciano

Another must-see destination in Tuscany is the charming town of Montepulciano, perched on a scenic hill that separates the Val d’Orcia and Val di Chiana valleys.

This town is home to Vino Nobile di Montepulciano, one of Tuscany’s finest red wines, which you can taste and purchase at local shops as you stroll through its streets.

The wine here isn’t just good – it’s life-changing. I ended up shipping a case home because I couldn’t bear to leave without it.

Montepulciano is also known for its stunning Renaissance residences, like the grand Palazzo Nobili–Tarugi, ancient churches, and lovely squares, with the main one being Piazza Grande – a perfect spot to soak in the town’s charm.

It’s no surprise that this picturesque location was featured in the movie “The Twilight Saga: New Moon”.

A standout landmark on Piazza Grande is the Palazzo Comunale, a 13th-century building that was later renovated to resemble the Palazzo Vecchio in Florence.

Climbing the palace tower is definitely worth it for the panoramic views of the valley (additional entry fee required).

On clear days, you can even see Lake Trasimeno and its islands, along with the surrounding peaks – a truly breathtaking sight! The climb is steep, but the views make every step worth it.

9. San Quirico d’Orcia

After exploring Montepulciano, it’s worth heading west to another picturesque village: San Quirico d’Orcia.

On the way, make sure to stop at a popular viewpoint that offers a peaceful view of a famous Tuscan villa, perfectly set among the rolling green hills. This is where I finally understood why Tuscany has inspired artists for centuries.

As you wander through San Quirico d’Orcia, don’t miss the town’s main attractions, including the medieval collegiate church and the elegant 17th–century Palazzo Chiggi.

10. Montalcino

The final place I’d recommend in Tuscany is the medieval town of Montalcino, perched on a majestic hill. Saving the best for last felt right – this town is pure magic.

This town is renowned for its world-class Brunello wine, which must age for at least five years before it reaches the market, with two years spent in oak barrels.

The patience required for this wine reflects the entire pace of life here- everything moves beautifully slowly.

Beyond the wine, Montalcino offers plenty of other attractions, such as the imposing medieval fortress, which hosts cultural events throughout the year, and the Palazzo dei Priori, overlooking the main square with its impressive clock tower.

If you’re into museums, don’t miss the Glass Museum or the Museum of Sacred Art, both worth a visit to explore the local culture and history.

No trip to Montalcino is complete without enjoying some local specialties along with a glass of fine red wine.

I highly recommend stopping by Trattoria l’Angolo da Cesare e Mara for delicious ravioli with ricotta and truffles, tender veal in aromatic red sauce, and sweet treats like panna cotta and tiramisu.

Every bite is a delight, and with Brunello wine, it’s simply perfect! The family running this place has been perfecting these recipes for generations, and it shows.

These Tuscan Treasures Changed How I See Italy

When I first planned my Tuscany trip, I thought it would just be another scenic Italian destination. I was so wrong. These ten towns didn’t just show me beautiful views – they taught me what it means to truly slow down and savor life.

From that first morning coffee in Greve in Chianti’s ancient square to my last glass of Brunello in Montalcino, every moment felt like discovering a secret that locals had been keeping for centuries.

The cobblestone streets under my feet, the warm greetings from shop owners, the way the light hits those medieval towers at sunset – these aren’t just tourist attractions, they’re invitations to experience la dolce vita.

Whether you’re craving that perfect pecorino cheese in Pienza or watching the sunset paint Montepulciano golden, these towns will give you memories that last a lifetime. They certainly changed mine.

Which Tuscan town speaks to your heart most? Have you fallen in love with any of these places yourself?

Share this guide with fellow Italy dreamers and tell me about your own Tuscan discoveries in the comments!

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