Top10 Hill Towns of Tuscany

Slender cypress trees, finely combed vineyards and fortified hilltowns, sitting enthroned on rolling hills, are the images that come to mind, when we picture Tuscany. Dating back to Medieval and even Etruscan times, these charming villages make history come alive with their rich heritage and generous architecture. Tuscany is an open-air museum, and hilltowns are the best places to get in touch with the historic ambiance of the region.

Boccaccio told tales about Certaldo in his Decameron and Dante described the imposing walls of Monteriggioni in his Divine Comedy. So poetic is the landscape and the hilltowns that conquer it, that it’s almost impossible to boil this list down to only 10. Here’s our effort:

San Gimignano

Already when you eye the first glimpses of San Gimignano, you realise its uniqueness
The charming Piazza della Cisterna is flanked by many historic buildings
The free museum San Gimignano 1300 is a must-see for every age!
Hike along the city walls to enjoy the magnificent views of the countryside
We recommend arriving in the afternoon and stay overnight, as to avoid the hordes in busses on their daytrip from Florence
Stay overnight to wake up to a scenery like this
San Gimignano doesn’t loose its charm together with declining temperatures
Its pencil-shaped skyline has earned it the nickname “Manhattan of the Middle Ages”
Piazza della Cisterna in the blue hours of the evening.
Stay overnight to experience a scenery like this

This Manhattan of the Middle Ages is an impressive sight to behold, when your car curves its way towards it through the Tuscan hillside. The pencil-shaped towers serve as lighthouses when hiking the landscape, guiding you safely back to this UNESCO World Heritage hilltown, where time has stood still. Although it is heavily trafficked by day-trippers arriving from Florence and Siena, it is most beautiful in the night time, where we love to sit in Piazza della Cisterna, surrounded by illuminated towers against a deep blue sky, listening to the swallows screaming.

Learn more about San Gimignano in our feature article about this towerful hilltown.

Volterra

Unjustifiably, Volterra has been standing in the shadow of UNESCO classed San Gimignano for many years
But this Etruscan enchantment is definitely worth a visit
It’s so quintessentially Tuscan that is has been used as a backdrop for many movies and TV shows
Volterra has acted as stand-for Florence in movies and TV-shows
The Palazzo dei Priori and the aptly named Piazza dei Priori is the heart of this hilltop town
The sumptuous decorated town hall in The Palazzo dei Priori is grand yet intimate
Volterra’s mind and spirit are the Etruscan museum, Pinacoteca and Civic museum
Discover the hilltown’s unique Etruscan heritage and rich art legacy
All we need in that picture is you, right?
The coats of arms honor the commissioners who governed the city

Unjustifiably, Volterra has been standing in the shadow of UNESCO classed San Gimignano for many years, but this Etruscan enchantment is definitely worth a visit. It’s so quintessentially Tuscan, that is has been used as a backdrop for many movies and TV shows, such as Medici – Masters of Florence, where it acts as stand-for Florence.

The Palazzo dei Priori and the aptly named Piazza dei Priori, is the heart of this hilltop town. Its mind and spirit are the Etruscan museum, Pinacoteca and Civic museum, that offer insights to its unique Etruscan heritage and rich art legacy. Volterra’s stomach is the area south and east of Piazza dei Priori and offers restaurants, cafés and enotecas.

Certaldo

Just a 20-minute ride north of San Gimignano, you encounter Certaldo
This is the final resting place of Italian poet and writer Boccaccio
Certaldo is also the setting for one of Boccaccio’s stories in his “Decameron”
Boccaccio wrote: “Certaldo is a little town in the Val d’Elsa. Although small, it was once the home of wealthy and noble people.”
While Certaldo has grown out of its boundaries, the fortified part on top of the hill is worth a visit
You can pay 1,5€ and take the funicular up the mountainside to save you the climb of 50 vertical metres
This charming village houses a Boccaccio museum, town hall, Sacred Art museum, a few churches and a couple of restaurants
Even though it’s cute, small and a picture perfect hilltown, it has resisted the temptation of becoming a tourist circus
The Medici Coat of Arms of Palazzo Pretorio dates back to 1538
Here, it’s easy to find a good spot for an al fresco lunch, peruse the valley below and let the stories of Decameron come alive

Located only 20 minutes north of San Gimignano, this final resting place of Italian poet and writer Boccaccio is also the setting for one of the stories in his Decameron.

“Certaldo, as you may possibly have heard, is a little town in the Val d’Elsa, in the hinterland of Florence. Although small, It was once the home of wealthy and noble people,” Boccaccio wrote.

While Certaldo may have grown out of its original, walled foundation and have spilled out into the valley, the fortified part on top of the hill is worth a climb and a visit. You can pay 1,5€ and take the funicular up the mountainside to save you the climb of 50 vertical metres. This charming village houses a Boccaccio museum, a town hall, a Sacred Art museum, a few churches and a couple of restaurants.

Even though it’s cute, small and a picture perfect hilltown, it has resisted the temptation of becoming a tourist circus and the small main road Via Boccaccia is pleasantly free from tourist shops. Here, it’s easy to find a good spot for an al fresco lunch, peruse the valley below and let the stories of Decameron come alive.

San Miniato

The village sits enthroned atop three small hills over the lower Arno valley
From La Rocca you can enjoy the beautiful views all the way to the sea in the west and the mountains in the north
San Miniato is famed for its white truffle and a visit is not complete without a truffle-infused lunch or dinner
The striking Seminario Vescovile
You can visit the splendid rooms of the town hall every weekend
The adjacent Cappella della Madonna di Loreto is a clash of colours
The Loggiati San Domenico is often busy
Don’t let the plain exterior of Santuario del Santissimo Crocifisso fool you
The façade of the Cathedral incorporates a number of colorful majolica bowls in an astronomical pattern

San Miniato is famed for its white truffle and a visit to this hilltown between Florence and Pisa is not complete without a truffle-themed lunch or dinner. Every year in November, the town comes alive for the international Truffle Market, where not only truffles, but all the splendid produce of Tuscany can be savoured. You can even go on a truffle hunt with locals. To learn how that turned out for us, follow us on our Hunt for the White Truffle of San Miniato.

The village itself sits enthroned atop three small hills overlooking the lower Arno valley. If you climb the cobblestone streets up to the La Rocca castle, you can enjoy the beautiful views all the way to the sea in the west and the mountains in the north. If you want an even better view, you can climb the ancient castle tower.

During summertime, the Tourist Office offers free guided tours on certain dates (booking necessary). On these events, and every Saturday and Sunday, you get to access the stunning rooms of the city hall and its colourful chapel of Madonna di Loreto. There is a lot to see and do – and eat! – in San Miniato, so even if you just stopped by on your way to or from Florence, you might just be wanting to stay.

Colle di Val d’Elsa

Gripping the oblong stretch of rock, Colle di Val d’Elsa balances above the waters of the Elsa river
As many other hilltowns, it spilled over its ancient walls and formed a new town below, but it’s the old part that is worth your attention
The landscape is truly Tuscan
You can almost FEEL the heat and HEAR the cicadas, right?
The lower, modern town has a market every saturday
The Parco Fluviale is a great hike along the cooling waters of river Elsa

Gripping an oblong stretch of rock, Colle di Val d’Elsa balances above the waters of the Elsa river, to which it owes its name. As many other hilltowns, it spilled over its ancient walls and formed a new town below, but it’s the old part that is worth your attention.

You enter is after leaving the car in the parking area in the valley below. Walking along the main street of this town that’s shaped like a finger, you arrive at its heart at Piazza del Duomo, that’s dominated not only by the cathedral but the Palazzo dei Priori as well. Continue your walk to the end of the old town at the panoramic balcony of Il Baluardo, that offers beautiful views to the new town below and the countryside.

Monteriggioni

On the road between Florence and Siena you will come upon this fortified hilltown
Monteriggioni is inspecting you as you approach, like it has done for no less than 800 years
This “borgo” was Siena’s line of defense against rival Florence
The fourteen towers you still see today were used in Middle Ages to patrol the area
You can walk along a little stretch of the ancient wall for 3€
Monteriggioni has perfectly preserved its structure
When Siena was ceded to Florence in 1555, it lost is military importance
It only functioned as a pilgrimage stop on the Via Francigena Pilgrimage road
It remained in perfect condition for the tourists of today, that come visiting this real life Medieval castle town

On the road between Florence and Siena, you will come upon this fortified hilltown inspecting you as you approach, like it has done for no less than 800 years. This borgo was Siena’s northern line of defense against rival Florence, and the fourteen towers you still see today, were used in the Middle Ages to control the area, overlooking the Cassia road between the two enemy city states.

It has perfectly preserved its structure, that is characterized by ten-meter-high fortified walls, built along the natural contour of the hill. You can walk along a little stretch of the ancient wall for 3€ and imagine how soldiers did so for hundreds of years back in the Middle Ages and the Renaissance. When Siena was ceded to Florence in 1555, it lost is military importance and so, little used, remained in perfect condition for the tourists of today, that come visiting this real life Medieval castle town.

Montepulciano

Famed for its Rosso di Montepulciano this small, wine producing town is also quite a moviestar, albeit for a younger audience
Montepulciano was used as stand-in for Volterra in the teenage vampire movie “Twilight”
It’s quite a steep climb up the cobblestoned streets to the centre of the town. But worth it.
This typical Tuscan town hall “Palazzo Comunale” was designed in the tradition of Palazzo Vecchio in Florence
The Medici family transformed the little mountain village to a centre of art
An “Enoteca” is an establishment, usually in a town, where you can sample wines from a wide variety of local wine estates
You can even find an underground city, with cellars dating back to medieval times
Ancient and Etruscan tomb stones adorning the facade of Palazzo Bucelli
The sigil of the Etruscans: A wine cup
The Art Nouveau café Caffé Poliziano is a wonderful place to catch your breath.

Famed for its Rosso di Montepulciano, this small, wine producing town is also quite a moviestar, albeit for a younger audience, as Montepulciano was used as stand-in for Volterra in the teenage vampire movie “Twilight”.

It’s quite a steep climb up the cobblestone streets to the centre of the town at the typically Tuscan town hall Palazzo Comunale, designed in the tradition of Palazzo Vecchio in Florence. But worth every step.

On your struggle to reach the very top of the hilltown from the parking lots at the outside of the city walls, you encounter wine shops, underground cellars dating back to medieval times, and artisan boutiques. Plenty of reasons to catch your breath and explore the history. Wait for your return to reduce the weight of your wallet and stock some local delicacies and full-bodied reds.

On our Wine Tour through Tuscany, we took a closer look at Montepulciano, so that’s worth a read if you want to know more about the hilltown and its wines.

Pienza

When driving from Montepulciano to Montalcino, you encounter the honey coloured hilltop town of Pienza
In the legendary landscape of Val d’Orcia, vineyards have given way to golden fields
This was the birthplace of later Pope Pius II
During his Papacy, he changed the medieval Castello di Corsignano into a Papal residence
Indeed, the entire village was rebuilt as an ideal Renaissance town
The town was renamed it after himself to Pienza
The town sits comfortably on top of a large hill and is easily accessible
It’s a comfortable stroll through the very orderly, bright town
Pienza offers spectacular views of the countryside
No wonder this perfect miniature Renaissance was named UNESCO World Heritage back in 1996

When driving from Montepulciano to Montalcino, you encounter the honey-coloured hilltop town of Pienza. You’re in the southern part of the legendary and UNESCO World Cultural classed landscape of Val d’Orcia, where vineyards have given way to golden fields of crops.

This soft, waving land was the birthplace of later Pope Pius II, that bejewelled his birth town. During his papacy, he changed the medieval Castello di Corsignano into a Papal residence in the Renaissance style. Indeed, the entire village was rebuilt as an ideal Renaissance town and renamed after himself to Pienza.

The town sits self-assured on top of a large hill and is easily accessible after you parked your car just outside the city walls. It’s a comfortable stroll through the very orderly, bright town, that offers spectacular views of the countryside. No wonder this perfect miniature Renaissance village was named a UNESCO World Heritage back in 1996.

Montalcino

Surrounded by vineyards and olive trees, this landscape has fathered some of the world’s best wines
Brunello di Montalcino: The wine, that made this small town famous
Visit the city’s largest tourist attraction, La Fortezza, a fortress from the 14th century, for a tasting
The inescapable clock tower of the Palazzo dei Priori is adorned with the rulers’ Coat of Arms
A visit to Montalcino is a rapid rendezvous
This small hilltop town of only 5.000 citizens is quickly conquered
No wonder, they make some of the world’s best wine: they’ve been at it since the 15th century
15 minutes drive south lies the Carolingian Abbey of Sant’Antimo

Brunello di Montalcino: The wine, that made this small town famous and swarmed with tourists in the summertime. No wonder they make some of the world’s best wine: they’ve been producing and refining Montalcino wines since the 15th century.

Visit the city’s largest tourist attraction, La Fortezza, a fortress from the 14th century, for tasting and purchasing the famous drops. At the Enoteca, you can enjoy a light lunch while tasting 2, 3, 5.. different Brunellos, Rossos or other SuperTuscans. Or you can just buy the wine by the glass to indulge in your very favourite. To know more about the wine and Montalcino, check out our article about Montalcino in Wine Touring Tuscany.

A visit to Montalcino is a rapid rendezvous, as this small hilltop town of only 5.000 citizens is quickly conquered. To prolong your stay in this charming wine country, take your car for a 15-minute spin down south to the Abbey of Sant’Antimo. This Carolingian monastery can date its roots back to the time of Charlemagne, and is beautifully set in a valley surrounded by hills and olive trees.

Cortona

Cortona is known for two things: Being the setting for Frances Mayes’ memoir “Under the Tuscan Sun” and the important museum of Etruscan history and culture
The small village is tucked away behind ancient walls and you must climb 50 vertical metres to the centre
Palazzo Casali still bears the Coat of Arms of its Florentine captains
The Museo dell’Accademia Etrusca e della Città di Cortona (MAEC) is an important museum
MAEC showcases many Etruscan artifacts
The rich heritage of the Etruscan civilisation will astound and amaze you
The museum also features Roman and Egyption artifacts and paintings
MAEC is really worth a visit, if not for its wonderful library
Despite its small size, Cortona has a lot to offer and the small square in front of the Town Hall just beckons to sit down with an espresso
The Cathedral of Cortona

This eastern-most of our Tuscan hilltown ensemble, Cortona is known for two things: Being the setting for Frances Mayes’ memoir “Under the Tuscan Sun” and the important museum of Etruscan history and culture; MAEC. Alright, perhaps it’s best known from “Under the Tuscan Sun” but the museum of MAEC is really worth a visit, if not for its wonderful library, which we featured in The Most Beautiful Libraries of Tuscany.

The small village is tucked away behind ancient walls, and you must park your car outside to venture into its steep streets, that climb 50 vertical metres to the centre, where the Town Hall crowns Cortona. Behind the Town Hall, Palazzo Casali features MAEC as well as the public library. It was occupied by the city’s Florentine captains back in early Renaissance and the coats of arms of these captains are still visible on the right hand façade of the building, on Via Casali, which has remained virtually unaltered.

Despite its small size, Cortona has a lot to offer and the small square in front of the Town Hall just beckons to sit down with an espresso and take in Tuscan everyday life, Preferably under the Tuscan sun.

Learn more

Tuscany’s official Tourism website
Discover Tuscany website
Tuscany of Italy´s official Tourism website
WeTuscany Rental Agency (comes highly recommended by us!)