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.
Tuscany isn’t just about Florence—it’s a region filled with stunning landscapes, world-famous vineyards, charming towns, and incredible food.
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.
Check out our guide to Tuscany’s most charming towns and start planning your unforgettable adventure. Have an amazing trip!
Table of Contents
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.
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.
The main charm of Greve in Chianti is Piazza Matteotti, a picturesque square surrounded by medieval buildings and a Franciscan monastery.
To soak in the town’s vibe, 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!
2. Montefioralle
The next village to explore in Tuscany is Montefioralle, tucked away among lush olive groves and vineyards.
Just a short distance from Greve in Chianti, its charming, narrow streets are perfect for a relaxed stroll.
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.
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.
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.
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 charming town captivates with its narrow streets and the delicious aromas wafting from the gardens of restaurants in the main square.
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.
Travel Budget Calculator
Get your free Travel Budget Calculator now and plan your trip without the stress of overspending!
5. Monteriggioni: One of the Most Beautiful Towns in Tuscany
Monteriggioni, sitting on a hill, is one of the most beautiful towns in Tuscany.
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.
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).
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.
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.
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!
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.
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.
8. Montepulciano: One of the Most Beautiful Towns in Tuscany
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.
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!
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.
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.
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.
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!
Travel Budget Calculator
Get your free Travel Budget Calculator now and plan your trip without the stress of overspending!
The 10 Most Beautiful Towns in Tuscany: Summary
Tuscany is an incredibly picturesque region, home to charming medieval towns that are some of the most beautiful in all of Italy.
If you love history and Italian cuisine, these towns should definitely be on your travel list. Their unique charm and delicious flavors will make you want to come back for more!
I hope this guide to the most beautiful towns in Tuscany has been helpful. If you enjoyed it, don’t forget to share it with your friends!
Have any favorite towns in Tuscany? I’d love to hear your recommendations—feel free to share them in the comments below!