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10 of the Most Enchanting Towns & Villages in Tuscany

One of Italy’s most famous regions, Tuscany is home to some of the most gorgeous little villages, where time seems to stand still. You could spend months in this magical area, so in this article, we’re sharing our insights into the very best towns in Tuscany.

Prepare yourself for some serious wanderlust as we journey through this breathtaking region to look at the history, culture, cuisine and inherent beauty of the small towns and villages that make Tuscany so iconic.

Florence, Tuscany and its famous Duomo seen in a panoramic shot

Image: Ultimate Driving Tours

What makes Tuscany’s towns and villages so special?

From rustic architecture to the slower pace of life, the villages and towns in Tuscany exude charm and will often be found at the top of a travel lover’s Italian bucket list.

Tuscany’s idyllic towns are among the world’s most postcard-worthy; nestled among rolling hills dotted with vineyards, olive groves and cypress trees, every cobblestoned corner leads you to another vista that halts you in your tracks.

But Tuscan towns are more than just pretty faces – they are rich with art, culture and history, boasting ancient roots and imposing architecture from mediaeval and Renaissance periods.

Naturally, the bigger cities like Florence, Livorno and Pisa are world-class travel destinations, but the smaller towns in Tuscany offer glimpses into another side of the culture. Thousands of years of history may give these locales their homely charm and heritage, but it’s the local communities that make the region’s hilltop towns such a pleasure to visit, with regular festivals, markets, crafts and tucked-away family restaurants.

On that note, as one of the world’s gastronomic epicentres, it’s in Tuscany’s tiny towns where many of the finest Italian dishes and wines originate. Classic reds such as Chianti, Brunello di Montalcino, and Vino Nobile di Montepulciano hail from Tuscan hill towns, as do the most exquisite truffles.

Yet it’s not only about the finer things in life, as many classic Tuscan dishes come from the philosophy of la cucina povera (kitchen of the poor); this is peasant food that can rival the satisfaction of Michelin-starred cuisine. Seek out simple dishes such as ribollita (bread soup) or panzanella (bread salad) – and thank us later.

Luckily, despite their popularity among tourists, many of the hill towns of Tuscany retain a sense of tranquillity. There is always an opportunity to relax and enjoy a slower pace of life, even in the height of tourist season, in July and August.

5 of the best Tuscan hill towns to visit

Each town in the region possesses its own hallmarks within the realms of beauty, history and cuisine, so selecting the best towns to visit in Tuscany is no simple matter. But that won’t stop us, so here are five of our handpicked favourites – towns we could visit year after year and never tire of.

San Gimignano, Tuscany sitting atop the green hills

Image: Ultimate Driving Tours

San Gimignano

Our number one pick is San Gimignano, which is one of the most beautiful towns in Tuscany, a UNESCO World Heritage Site, and a culinary gem. Set in the province of Siena, the defining feature of this walled mediaeval hill town is its preserved tower houses, of which there are around a dozen. The 54-metre Torre Grossa is well worth the climb for the stunning views of the surrounding Val d’Elsa, which is where you’ll find some of our favourite hotels in Tuscany. Don’t miss stopping for a lick of one of Italy’s best gelatos at Gelateria Dondoli.

Old stone buildings and a clocktower in Cortona, Tuscany

Image: Gabriella Clare Marino on Unsplash


Located in southern Tuscany, Cortona is widely accepted as one of the most beautiful places in the region. This unspoiled ancient hilltown boasts typically magnificent views, a picturesque town square, quaint winding streets and a renowned Etruscan museum. Grab a coffee in the Piazza della Repubblica and enjoy an afternoon of people-watching at its finest. With such charm and beauty, it’s no wonder that Cortona was the setting of the 2003 romantic comedy film, Under the Tuscan Sun.

Montalcino, Tuscany overlooking sweeping green valleys



We can’t list the best towns in Tuscany and not mention Montalcino, which is the place to visit if you love Italian wine – and, let’s face it, who doesn’t? Nestled in the Val d’Orcia in the province of Siena, this hilltop town is known for the prestigious Brunello variety. Like other towns on this list, Montalcino also offers much to see in the way of history and culture. Today, the tower of the mediaeval fortress has been converted into a wine bar, Enoteca la Fortezza, allowing you to be immersed in the location’s unique history between sips.

Montepulciano seen from below with red brick buildings, clay roofs and cloudy sky.



Surrounded by vineyards, the gorgeous Montepulciano is another important hilltop town in the world of Italian wines. Most intriguing, this town has an ‘underground city’ thanks to a network of hidden tunnels, crypts and cellars three floors below street level – naturally, the perfect places to enjoy a glass or two of Vino Nobile. There’s also plenty of Montepulciano to explore in terms of mediaeval architecture, long scenic streets, a climbable clock tower, and traditional Tuscan cuisine.

A hilltop town in Tuscany perched above forests and paddocks.


Casole d’Elsa

Another of our favourites, Casole d’Elsa is a heavenly Tuscan town with sweeping views of the Sienese countryside. In the Val d’Elsa, this romantic artisan town has a lot to offer besides beauty, including the 14th century fortress-turned-local town hall, two churches, and an abundance of intriguing street artwork over which to muse. You will also find plenty of local pizzerias, enotecas and gelaterias to satisfy your hunger for Tuscan cuisine.

5 hidden gem and off-the-beaten-path Tuscan villages

With the more popular towns in Tuscany covered, we now move on to some of our favourite hidden gems and villages that can be discovered by venturing off the well-worn tourist path.

Pienza, Tuscany with cypress trees, ornate stone buildings and verdant hills.



Once known as Corsignano, Pienza was the birthplace of Pope Pius II, who requested the town be rebuilt to become the ‘ideal Renaissance city’ in the 15th century. While building halted after the death of the pope, the UNESCO World Heritage Site provides a glimpse at what the perfect town may be. Not only does it offer a sense of idealism within the town walls, but Pienza also offers special views of Val d’Orcia – portrayed as paradise in the 2000 blockbuster movie Gladiator. Foodies will enjoy visiting the ‘capital of pecorino cheese’ in September for the annual cheese festival.

Anghiari, Tuscany seen from above as it is illuminated in the evening sky.



Anghiari is a remarkable old Tuscan village hidden deep in the countryside on the outskirts of the city of Arezzo. Inside the preserved 13th-century walls, Anghiari’s narrow cobblestone streets lined with ancient stone houses exude plenty of character. Art enthusiasts will enjoy wandering the studios and shops where local artisans offer crafts and antiques made from wood, textiles and ceramics. Interestingly, the town inspired Leonardo Da Vinci’s fresco The Battle of Anghiari for the Palazzo Vecchio in Florence, which was abandoned and then lost.

Cobble stone laneways and timber doors in Suvereto, Tuscany



One of the cutest towns in Tuscany, Suvereto is a tiny masterpiece in the gallery of the Val di Cornia. Set among chestnut and cork woodland, this peaceful mediaeval village is a pleasure to visit if you are on the hunt for some respite. Meander through the streets and admire adorable stone houses, tranquil churches and the restored fortress, La Rocca Aldobrandesca, which offers postcard-perfect views of the surrounding woods and olive groves.

Natural hot waterfalls and old stone buildings of Saturnia, Tuscany



Sitting in the southern province of Grosseto, Saturnia is a tiny Tuscan hamlet that was home to the ancient Greeks, Etruscans, and Romans, and now has a population of around 280. The compact village itself is peaceful and picturesque, although it’s the thermal springs that make Saturnia worth the visit. Capitalising on the healing thermal waters, the area now has two luxurious wellness centres boasting all the modcons, although you will also find two natural 37°C (99°F) waterfalls that are free to use.

Cliff-top buildings in Pitigliano, Tuscany seen on a golden evening.



Saving the best for last? Quite possibly, at least in terms of awesome scenery, as the old Tuscan village of Pitigliano offers some of the most photogenic landscapes. From outside, the town appears suspended in midair due to its unique positioning on volcanic tufa rock. Inside, Pitigliano is just as special, with exceptional architecture including houses, churches, a synagogue, and excavated roads; the purpose of which still baffles historians today.

A red Ferrari 488 and yellow Mercedes-AMG GT on an Ultimate Driving Tours journey.

Image: Ultimate Driving Tours

Discover Tuscany’s hidden gems as part of a luxurious supercar tour

Whether you want to soak in the beauty of the famous rolling hills or sample the finest wines in Chianti, you can breathe in the best of Tuscany with our extraordinarily luxurious Tuscan supercar driving tour.

Over seven days, enjoy an adventure traversing the Tuscan countryside in a fleet of latest-release supercars, visiting some of the region’s finest restaurants and relaxing in a curated series of historic five-star properties. There’s simply no better way to experience this renowned region.

If you’d like to learn more about this Tuscan expedition or any of our exclusive European tours, speak to our friendly travel concierge team today.

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