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Experience the most beautiful towns in Tuscany, a destination unlike any other.
Nestled in Italy, this enchanting region boasts an array of attractions, from its picturesque landscapes and renowned vineyards to its delectable cuisine.
If you’re planning a holiday in Tuscany, don’t miss the opportunity to explore its wonders by renting a car and embarking on a memorable journey through the area.
To assist you in your travels, we’ve curated a list of the top 10 most beautiful towns in Tuscany that deserve a spot on your itinerary.
Discover the must-see sights of Tuscany and let our recommendations ignite your wanderlust! Happy reading!
Table of Contents
1. Greve in Chianti: One of the Most Beautiful Towns in Tuscany
The first town you should consider visiting in Tuscany is the picturesque Greve in Chianti, nestled in the province of Florence, one of the most beautiful towns in Tuscany.
The town derives its name from the river running through it and the renowned wine region it belongs to.
Its primary allure lies in Piazza Matteotti, a square encircled by numerous medieval structures and a Franciscan monastery.
To fully immerse yourself in the town’s ambiance, I suggest stopping by one of the cafes situated in the square and indulging in a cup of delicious coffee.
It’s the perfect way to kick off a truly Italian day!
2. Montefioralle
The next village worth exploring in Tuscany is Montefioralle, nestled among verdant olive groves and scenic vineyards.
Situated near Greve in Chianti, its narrow, quaint streets beckon for leisurely strolls.
This locale is truly enchanting and merits a visit, particularly for the breathtaking views that surround the village.
Consider planning your visit for March when the village outskirts host the Festa di Fritelle, offering a chance to sample various local delicacies.
Given the limited parking spaces in the village, it’s advisable to consider walking from Greve in Chianti, a journey that should take no more than 30 minutes.
3. Panzano in Chianti
Another must-visit destination in Tuscany is the town of Panzano in Chianti, nestled at an elevation of nearly 500 meters.
This town is primarily renowned for hosting the annual Vino al Vino festival, held every third weekend in September, as well as the famed butcher shop of Dario Cecchini, where visitors can savor the perfect bistecca alla fiorentina.
Among the town’s other attractions is its medieval castle, serving as both the oldest and tallest building in Panzano, and the nearby church of San Leolino, showcasing works by artists such as Giovanni della Robbia and Raffaelino del Garbo.
4. Radda in Chianti
After exploring Panzano, it’s worth venturing further south to the medieval village of Radda in Chianti.
This town captivates with its narrow streets and entices with the aromas drifting from the gardens of restaurants on the main square.
Make sure to reserve some time for lunch or dinner at La Bottega di Giovannino restaurant.
I highly recommend trying dishes such as: traditional hearty ribollita bean soup, ricotta ravioli in an aromatic sage sauce, mushroom gnocchi, and panna cotta with fruits.
All the dishes taste superb here, and a glass of red wine perfectly complements their flavors.
5. Monteriggioni: One of the Most Beautiful Towns in Tuscany
Monteriggioni, perched atop a majestic hill, is undeniably one of the most beautiful towns in Tuscany.
This locale boasts an impressive fortress, erected by the residents of Siena in the early 13th century, featuring fourteen towers.
The primary purpose of the fortress was defense against attacks from nearby Florence and Volterra (remarkably, the fortress remained unconquered for nearly several hundred years!).
While the entire town can be explored in just a few minutes, it’s worth lingering longer, especially to indulge in the delicious ice cream at Gelateria La Bottega del Castello.
Of particular note is the main square, Piazza Roma, adorned with the Romanesque church of Santa Maria Assunta, as well as the remarkably well-preserved city walls. Platforms have been constructed atop these walls for tourists to admire the breathtaking views of the surrounding area (additional entry fee required).
The town’s beauty and charm have made it a popular backdrop for numerous films, commercials, and even well-known computer games.
Dante himself mentioned Monteriggioni in his “Divine Comedy.” Considering its stunning vistas, it’s easy to understand why.
6. Pienza
When visiting Tuscany, you simply cannot overlook one of Europe’s most picturesque wine regions – the Val d’Orcia Valley.
Stretching from the hills south of Siena to Monte Amiata, it is renowned for its magnificent landscapes adorned with charming medieval towns.
For this reason, the region has earned a place on the UNESCO World Heritage List.
A notable gem within this area is the charming town of Pienza.
Once a modest Tuscan village, Pienza was partly transformed into a utopian vision of the “ideal Renaissance city” by Pope Pius II, who hailed from the region.
Thanks to the efforts of exceptional architects, today we can marvel at 15th-century structures such as the Duomo, Palazzo Comunale, and Palazzo Piccolomini, all offering breathtaking views of the valley.
It was within the gardens of this palace in the 1960s that a film depicting the story of Romeo and Juliet, which won two Oscars, was filmed.
You can also take in the stunning landscapes by wandering along Via dell’Amore and the streets behind the cathedral.
In addition to the mentioned landmarks, it’s worth visiting the Romanesque church of Pieve di Corsignano located on the outskirts of the town.
Since Pienza is also renowned for its delicious sheep products, a must during any trip is purchasing pecorino cheese from one of the local shops.
Various flavor profiles and maturity levels (ranging from several to several dozen months) are offered, allowing everyone to find the right cheese for themselves.
If you’re visiting Pienza, be sure to reserve time for lunch at one of the local restaurants, such as Trattoria da Fiorella.
I recommend trying pecorino cheese with red radicchio (Italian chicory) and for the main course – handcrafted taglierini with duck in a delicate white sauce. It’s a delight for the palate!
7. Monticchiello
After exploring Pienza, it’s worthwhile to venture to another charming village nestled in the Val d’Orcia valley – the medieval hamlet of Monticchiello.
During your journey, I recommend making a stop at the viewpoint – Photo Spot Toscana. From there, you can admire one of Tuscany’s most iconic landscapes – the winding avenue of cypress trees, gracefully winding through verdant hills, providing the perfect backdrop for unforgettable photographs.
While Monticchiello itself doesn’t offer too many attractions, it’s worth a brief visit, primarily for the stunning views that unfold from there and the historic church of Santi Leonardo e Cristoforo.
8. Montepulciano: One of the Most Beautiful Towns in Tuscany
Another significant destination not to be missed in Tuscany is the charming town of Montepulciano, perched atop a scenic hill that separates two valleys – Val d’Orcia and Val di Chiana.
This is where one of Tuscany’s finest red wines, Vino Nobile di Montepulciano, originates from the local vineyards. While strolling through Montepulciano’s streets, you’ll easily find shops offering tastings and sales of this renowned wine.
The town itself is also renowned for its many Renaissance residences, such as the majestic Palazzo Nobili-Tarugi, ancient churches, and charming squares, with the main one being Piazza Grande, which only adds to the allure of the place.
It’s no wonder, then, that less than a decade ago, scenes for such a cinematic hit as “The Twilight Saga: New Moon” were filmed here.
Standing proudly on Piazza Grande is another significant landmark of the town – Palazzo Comunale. This building, erected in the 13th century, was later renovated to resemble the Palazzo Vecchio in Florence by an architect from the Medici family.
Ascending the palace tower is well worth it, as it offers splendid panoramic views of the entire valley (additional entry fee required).
On clear days, you can even catch a glimpse of the nearby Lake Trasimeno with its islands, as well as the surrounding peaks. Truly a sight to behold!
9. San Quirico d’Orcia
After exploring Montepulciano, it’s worth venturing further west towards another picturesque village, undoubtedly San Quirico d’Orcia.
Along the way, make a stop at the popular viewpoint, offering a serene view of the famous Tuscan villa, nestled amidst the green hills.
While wandering through San Quirico d’Orcia, be sure to visit the town’s main attractions, including the medieval collegiate church and the 17th-century Palazzo Chiggi.
10. Montalcino
The final place I’d like to recommend to you in Tuscany is the medieval town of Montalcino, situated atop a majestic hill.
Its renown and wealth are primarily attributed to the world-class Brunello wine, which, before hitting the market, must mature for at least five years (with two years spent in oak barrels).
However, aside from its delectable red wine, the town offers other attractions such as the imposing medieval fortress, which serves as the backdrop for various cultural events during the season, and the Palazzo dei Priori overlooking the main square – the town hall with its impressive clock tower.
It’s also worthwhile to visit one of the local museums – you have the option of the Glass Museum or the Museum of Sacred Art.
No trip to Montalcino would be complete without relishing in local specialties accompanied by superb red wine.
I highly recommend Trattoria l’Angolo da Cesare e Mara restaurant, where you can sample delicious ravioli with ricotta and truffles, succulent veal in aromatic red sauce, and heavenly panna cotta and tiramisu.
Every bite melts in your mouth, and when paired with such fine wine as Brunello, it tastes even more exquisite!
Conclusion: One of the Most Beautiful Towns in Tuscany
Tuscany is an exceptionally picturesque region of Italy, boasting many charming medieval towns, including some of the most beautiful towns in Tuscany.
If you’re a fan of both historical landmarks and Italian cuisine, you should definitely include at least a few of them in your travel itinerary.
Rest assured that their charm and flavors will leave you longing to return!
I hope this travel guide to the most beautiful Tuscany towns has proven helpful. If so, I would appreciate it if you could share this article with your friends.
And which towns in Tuscany do you recommend? Please share your suggestions in the comments below!