€10 credit on 2+ art prints in my shop
Visit Southern Tuscany's Dreamiest Spots
Uncover breathtaking hill towns and landscapes in southern Tuscany and the Val d'Orcia.
by Sonja | Artist & MA Interior Architecture
7 min. read
| Update:
3 Jun 2026
Created 19 January 2026
© 2026 Sonja Travel Artist
Waking up in a traditional Tuscan villa with views over rolling hills in morning light
Southern Tuscany, including the scenic Val d’Orcia, is home to what I’d consider the quintessential Italian countryside: historic towns rising from rolling hills, elegant villas nestled among vineyards, and cypress-lined roads winding through breathtaking landscapes. As a Mediterranean-inspired artist, visiting a region so rich in character and tradition felt like a dream come true — vast landscapes, soft light, and seemingly endless inspiration. Join me in discovering five of the most beautiful places in southern Tuscany and the Val d’Orcia.
1. The Rolling Hills of the Val d 'Orcia
Tuscan countryside
Panoramic views
The Val d’Orcia is one of the most picturesque regions of Tuscany that I’ve explored by car. It’s well worth the drive, as you can stop spontaneously whenever a breathtaking view catches your eye. Immerse yourself in the idyllic charm of the Italian countryside, from picturesque hilltop villages to unforgettable panoramic viewpoints. Here's what you need to know about the Val d’Orcia:
What's the Val d'Orcia? The Val d’Orcia is a valley in Southern Tuscany, named after the Orcia River that flows through it. The region was declared a UNESCO World Heritage Site in 2004, as it's considered a prime example of a cultural landscape shaped by Renaissance ideals.
What can I see in the Val d'Orcia? The Val d’Orcia is famous for its excellent wine and scenic viewpoints, and it's also home to several natural hot springs as well as numerous beautiful towns like Pienza and Montepulciano. I’ll cover more details on these in the following points.
Best viewpoints in the Val d'Orcia? Just south of Pienza, the famous Gladiator filming location transports you back in time — almost as if you’ve stepped into the movie yourself. Another inspiring spot is the Cipressi di San Quirico, a serene cluster of cypress trees on the hills.
2. Pienza Hill Town
Renaissance era
Tuscan architecture
Pienza, scenically perched on a hill overlooking the Val d’Orcia, enchanted me with its charming streets and terraces offering stunning views of rolling hills and cypress trees. As an artist, I was particularly drawn to its fascinating history, which sets it apart from many other towns in the region. Originally known as Corsignano, Pienza was renamed by Pope Pius II, who was born there, as part of his ambitious vision to transform the town according to Renaissance ideals in the 15th century.
Key Sights in Pienza:
Piazza Pio II – The heart of Pienza and the centrepiece of Pope Pius II’s Renaissance vision for the town. Its elegant historic buildings and harmonious Renaissance layout particularly stood out to me.
Santa Maria Assunta Cathedral – Adjacent to Piazza Pio II, this Renaissance cathedral is one of Pienza’s most important landmarks. I loved its peaceful interior, featuring cross vaults and three naves of equal height.
Palazzo Piccolomini – Built as the residence of Pope Pius II, this elegant Renaissance palace stands beside Piazza Pio II. If you have time, I’d recommend exploring its beautifully preserved rooms and peaceful garden.
Palazzo Comunale – You’ll recognise Pienza’s historic town hall by its graceful arcades and striking bell tower overlooking Piazza Pio II. From here, you also get one of the most beautiful views of the square.
Palazzo Borgia – Originally gifted by Pope Pius II to Cardinal Rodrigo Borgia, the palace now houses the Museo Diocesano, where you can explore a collection of religious art and historical artefacts.
Mediterranean Traveller Newsletter —
Italy, Art & Travel
Join the mailing list and be the first to discover the following highlights:
1. My latest inspiring travel stories
2. New Mediterranean art for your home
3. Limited editions & travel journals
3. Montepulciano's Medieval Alleys
Medieval Tuscany
Tuscan architecture
Montepulciano captivated me with its medieval townscape, shaped by narrow, winding streets and an imposing castle. Just a little outside the Val d’Orcia, it feels more organically grown compared to Pienza which is just twenty minutes away by car. You could easily visit both towns in a single day, allowing you to experience two different sides of Tuscany: Pienza with its carefully planned Renaissance architecture, and Montepulciano with its grown, medieval character.
Key Sights in Montepulciano:
Piazza Grande – After wandering through Montepulciano’s narrow, steep alleys, the city’s main square surprised me with its spacious, open feel. I loved the Renaissance fountain next to Palazzo Nobili-Tarugi.
Santa Maria Assunta Cathedral – Though built in the 15th century during the Renaissance, the cathedral resembles a more medieval structure due to its raw brick façade, which was never clad in stone.
Medici Fortress – Explore the peaceful courtyard and quiet garden with sweeping views at Montepulciano’s fortress. In the on-site wine bar, you can also try the famous Vino Nobile di Montepulciano.
4. Hot Springs in Southern Tuscany
Bagni San Filippo
Terme di Saturnia
Have you ever bathed in the mineral-rich mud of a steaming thermal spring? In southern Tuscany, you can. Thanks to its proximity to the dormant volcano Monte Amiata, the region is home to numerous hot springs. These waters have been treasured for centuries, valued by both the Etruscans and Romans for their healing properties. In the Val d’Orcia, I'd recommend Bagni San Filippo, where cascades of steaming water wind quietly through a lush forest. A more well-known alternative is the Saturnia hot springs, although they are further away from the Val d’Orcia and can be busy during peak season.
Personal travel note: Please remember that these springs are rare and fragile, so enjoy them responsibly. Treating them with care helps preserve their beauty for everyone to experience.
5. Discover Abbazia San Galgano
Tuscany landmarks
Tuscan abbey
The Abbazia di San Galgano, located a few kilometres north of the Val d’Orcia, is a Gothic monastery ruin that has captivated me with the remarkable sight of its roofless nave. Its pointed arches and slender columns rise towards the sky in a way that feels both dramatic and serene. The church lost its roof after the bell tower collapsed in the 18th century, and today wandering through the ruins makes for quite a spine-tingling experience. At the same time, the site offers a wonderful glimpse into rural medieval life in Tuscany.
Experience the Soul of Southern Tuscany
Southern Tuscany and the Val d’Orcia have enchanted me with their breathtaking landscapes and rich cultural heritage. From charming hill towns to hot springs, the region offers a wide range of experiences that suit your own way of travelling – whether solo or with others. If you wish, you can extend your stay to another of Tuscany’s top destinations such as Florence or Pisa. No matter which destination you choose, Tuscany offers a travel experience that nourishes both mind and soul.
Practical Tips for Tuscany — FAQ
1. What sets southern Tuscany apart from northern Tuscany?
Southern Tuscany has a more rural character, defined by rolling landscapes, small hill towns and agricultural estates. Northern Tuscany, by contrast, is more urban and historically shaped by powerful city-states, with cultural centres such as Florence and Pisa playing a key role in art, trade, and politics.
2. How can I explore southern Tuscany efficiently?
I’d recommend choosing a car, as there are lots of small towns and scenic spots you can reach flexibly. If you’re up for a little adventure, you could also rent a Vespa (at your own risk). Not every town in the Val d’Orcia has a train station, though there is a train connection between Siena and Montepulciano.
3. What should I know before visiting southern Tuscany?
A few things might surprise you! Some roads are very rocky, so take care if you’re renting a car. Also, be aware of wildlife, especially at dusk — deer, wild boars, and owls can appear unexpectedly on the roads. Tuscany is also home to European scorpions: while their sting isn’t considered dangerous, it can be painful, so watch your shoes and luggage.
