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Tuscan Countryside — 5 Dreamy Places in Val d’Orcia & Beyond
Waking up in a traditional Tuscan villa with views of the rolling Tuscan countryside
The Tuscan countryside is home to what I’d consider the quintessential Italian postcard-perfect landscape: historic towns rising from rolling hills, elegant villas nestled among vineyards, and cypress-lined roads winding through breathtaking landscapes.
As an artist, visiting a place so rich in character and tradition felt like a dream come true — vast landscapes, soft light, and seemingly endless inspiration. From charming villages to breathtaking viewpoints, there’s a wonderful variety of things to see.
As one of the most distinctive parts of Tuscany, the Val d’Orcia will be the focus of this post — but there’s more to explore. Join me in discovering my favourite places for a true Tuscan countryside experience.
1. Val d’Orcia: The Dreamiest Valley in the Tuscan Countryside
The Val d’Orcia, not far from Siena in southern Tuscany, is the epitome of idyllic Italian countryside life. Characterised by winding roads and rolling hills, the region was declared a UNESCO World Heritage Site in 2004. It was named after the Orcia River that flows through it and boasts a truly unique cultural heritage.
History is partly responsible for the Val d'Orcia's dreamy appearance: During the 14th and 15th centuries, the merchants of Siena shaped the agricultural landscape according to Renaissance ideals, giving it the iconic appearance it is known for.
The best way to explore the Val d’Orcia is by car. It’s well worth the drive, as having your own car allows for spontaneous stops whenever a breathtaking view catches your eye. Public transport connections are limited.
CAMPI ELISI (GLADIATOR)
Just south of the hilltop town of Pienza, the famous Gladiator filming location transports visitors back in time. From here, a solitary path winds through the rolling Tuscan hills towards a remote villa. Find the exact Gladiator filming location here.
CIPRESSI DI SAN QUIRICO
This famous viewpoint features two iconic spots in Tuscany: the Bosco di Cipressi, a small solitary forest, and the Cerchio dei Cipressi, where cypress trees are arranged in a perfect circle.
A visit here can easily be combined with a trip to the town of San Quirico d’Orcia. Find the exact Cipressi di San Quirico location here.
2. Pienza: Renaissance Gem in the Tuscan Countryside
The Renaissance hilltop town of Pienza enchants with carefully planned streets and terraces, opening up to breathtaking views of the Tuscan countryside. Located in the scenic Val d'Orcia, its historic centre was declared a UNESCO World Heritage Site.
Pienza was originally known as Corsignano, but was renamed by Pope Pius II as part of his ambitious vision to transform the town according to Renaissance ideals in the 15th century. Pope Pius II was born in Pienza, which is why the town was of particular importance to him and his
family’s prestige.
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 stand out in particular.
SANTA MARIA ASSUNTA CATHEDRAL
Adjacent to Piazza Pio II, this Renaissance cathedral is one of Pienza’s most important landmarks. Its peaceful interior features 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 there's time, it's recommended to explore its beautifully preserved rooms and peaceful garden.
PALAZZO COMUNALE
Pienza’s historic town hall is recognisable by its graceful arcades and striking bell tower overlooking Piazza Pio II. From here, one of the most beautiful views of the square opens up.
PALAZZO BORGIA
Originally gifted by Pope Pius II to Cardinal Rodrigo Borgia, the palace now houses the Museo Diocesano, where a collection of religious art and historical artefacts can be explored.
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3. Montepulciano: Medieval Charm and Winding Alleys
Montepulciano pulls visitors in with its medieval townscape, characterised by winding alleys and an imposing medieval fortress rising from the highest point of the town. In contrast to Pienza, it feels quainter and more organic, with steep streets and stairs continuously leading uphill.
Both Pienza and Montepulciano can easily be visited in a single day, allowing visitors to experience two hill towns in the Tuscan countryside with very different characters.
PIAZZA GRANDE
The city’s main square surprises with its spacious, open feel, standing in striking contrast to the narrow alleys surrounding it. The Renaissance fountain next to Palazzo Nobili-Tarugi is a particularly beautiful detail.
CATTEDRALE DI SANTA MARIA ASSUNTA
The main church of Montepulciano was built in the 15th century during the Renaissance. However, because its raw brick façade was never clad in stone, the cathedral has a more medieval appearance.
MEDICI FORTRESS
The peaceful courtyard and quiet garden at Montepulciano’s fortress offer sweeping views over the surrounding hills. The on-site wine bar also serves tastings of the famous Vino Nobile di Montepulciano.
4. Hot Springs: Natural Wonders of the Tuscan Countryside
The Tuscan countryside is home to numerous hot springs, thanks to its proximity to the dormant volcano Monte Amiata. These waters have been treasured for centuries, valued by both the Etruscans and Romans for their healing properties.
Especially in the Val d’Orcia and southern Tuscany, I’d recommend visiting 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 can get 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. Abbazia San Galgano: A Glimpse of Rural Life in Tuscany
The Abbazia di San Galgano, located a few kilometres north of the Val d’Orcia, is a Gothic monastery ruin that impresses with its remarkable 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.
Personal travel note: Here's a Google Maps link to the exact Abbazia San Galgano location.
A True Tuscan Countryside Experience
The Tuscan countryside is the perfect place to slow down, get inspired, and enjoy both culture and nature. Southern Tuscany, especially the area around the Val d’Orcia, is truly diverse, ranging from charming hill towns to hot springs, making it a great choice for travelling solo or in groups.
Looking back on my own trip through Tuscany as an artist, these five dreamy places in the Tuscan countryside gave me a truly well-rounded glimpse into the heart of the region.
Pair these places with a gentle hike through the rolling hills or a wine-tasting experience at one of Tuscany’s agriturismos, and you’re good to go!
Essential Tips for Your Stay in the Tuscan Countryside
1. When is the best time to visit the Tuscan countryside?
Spring is especially beautiful in Tuscany, with poppies, roses, and wisteria in bloom, while autumn offers warm light and lingering late-summer temperatures.
2. What’s the best town to stay in the Tuscan countryside?
Siena is a great base thanks to its excellent train connections and rich cultural heritage. Other towns in southern Tuscany, such as Pienza or Montepulciano, are charming but require a car to get around.
3. How long should you stay in the Tuscan countryside?
At least a week is ideal to savour Tuscany’s rural atmosphere and explore some of its most remarkable places.
4. Which is more beautiful, Pienza or Montepulciano?
Pienza stands out from many other towns in the Val d’Orcia thanks to its carefully planned Renaissance architecture. Both Pienza and Montepulciano, however, offer beautiful views and a charming historic atmosphere.
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