Tuscany is one of those Italian regions that immediately captures the imagination. From the very first kilometres, the landscapes seem almost unreal: hills covered in cypress trees, roads winding through vineyards, hilltop villages with stone facades bathed in golden light… Here, every turn feels like stepping into a postcard.
But Tuscany is more than just beautiful scenery. It has a very special atmosphere — small, lively squares where life moves slowly, family-run trattorias serving simple yet incredibly flavoursome food, and markets full of local produce to enjoy without restraint!
During our road trip, we fell completely in love with this unique art de vivre. We spent several days exploring the roads in our motorhome and were truly captivated by this magnificent region. It’s incredibly easy to get swept up in the dolce vita atmosphere, the stunning scenery and the countless cypress trees so characteristic of Tuscany.
Between stone houses, olive trees as far as the eye can see, golden fields and world-famous vineyards, Tuscany offers a unique atmosphere you simply won’t find anywhere else.
Food-wise, it’s hard not to fall in love with the region. Fresh pasta, wood-fired pizza, local charcuterie, cheeses, artisan ice cream and the famous Tuscan wines — every meal becomes a truly memorable experience. Even the tiniest villages often hide incredible restaurants where you can eat wonderfully well at still very reasonable prices.
And if you’re a truffle lover, Tuscany is absolutely the destination for you! You’ll find them everywhere: in restaurants, specialist shops and local markets, often at very reasonable prices. It’s the perfect opportunity to indulge almost endlessly throughout your trip!
Tuscany also boasts an exceptional cultural heritage. A land of artists and the birthplace of the Renaissance, it is rich in historical treasures, impressive cathedrals, medieval alleyways and villages listed among the most beautiful in Italy. Whether you love history, photography, hiking, food or simply beautiful landscapes, this region manages to win over absolutely everyone.
In this article, we’ll take you to discover the Tuscan villages that left the biggest impression on us during our road trip — their atmospheres, their must-sees and all the little details that make this region so magical. Much like our favourite medieval villages in Brittany.
San Gimignano
No visit to Tuscany would be complete without a stop at San Gimignano. Perched on a hill amid the region’s typical landscapes, this medieval village is undoubtedly one of the most famous and recognisable in Tuscany, thanks to its impressive stone towers that dominate the entire skyline.
The great peculiarity of San Gimignano is precisely its famous medieval towers. In the past, the wealthiest families in the town would build ever-taller towers to display their power and wealth. There were once more than 70 of them! Today, 14 towers are still perfectly preserved and give the village an absolutely unique silhouette in Tuscany. No matter where you are around the town, they immediately catch the eye and add enormously to its charm.
From the moment you arrive, you fall immediately under the spell of its ramparts, cobbled streets, lively little squares and remarkably well-preserved historic buildings. The village is relatively small, but there is an enormous amount to see and above all a truly special atmosphere that makes you want to take your time.
We absolutely loved this magnificent village — our favourite of the whole trip. Allow a good half day to stroll and get lost in the alleyways — that’s the one piece of advice we’ll give you! The village is very touristy, but as soon as you step away from the main street, you have it all to yourself. There are plenty of food shops where you can pick up regional specialities: wine, truffles and wild boar sausage! And yes, if you see wild boars everywhere — in soft toys or drawings — that’s perfectly normal! It’s something of the town’s emblem. Don’t leave without trying some!
During your visit, take the time to discover Piazza della Cisterna, probably the most beautiful square in the village with its medieval facades and numerous cafés and restaurants. Just next door, Piazza del Duomo is also well worth a visit, with its magnificent collegiate church and impressive frescoes.
One of the best things to do in San Gimignano is simply to wander with no particular destination in mind. Every alleyway hides a pretty facade, a small artisan shop, a wine cellar or a magnificent viewpoint over the Tuscan countryside. Photography enthusiasts are in for a real treat here.
If you love beautiful panoramas, you can also climb to the top of some of the towers open to the public to admire the Tuscan hills and vineyards stretching as far as the eye can see. The view over the surrounding landscape is absolutely magnificent, especially at the end of the day when the light turns golden.
A sense of wonder we also felt in the Cotswolds in England.
Siena
Siena is without doubt one of the most beautiful cities in Tuscany. With its historic centre listed as a UNESCO World Heritage Site, its charming medieval alleyways and its elegant atmosphere, the city has a truly distinctive identity that immediately sets it apart from the region’s other villages and towns.
Everything here seems to have retained its authenticity. You wander through a real labyrinth of narrow cobbled streets lined with warm-toned facades typically Tuscan in character, past artisan shops, cafés, hidden little squares and impressive historic buildings.
The heart of the city is of course the famous Piazza del Campo, probably one of the most beautiful squares in Italy. Its unique shell shape and vast open space give it a truly impressive atmosphere. This is where the famous Palio di Siena takes place — a historic horse race held several times a year and followed with incredible passion by the locals.
We loved our visit to Siena, especially the central square with its palace, its shell shape, its atmosphere and above all its colours! What a wonder — that blend of ochre, pink and earth tones… and it’s even more beautiful in the evening when the sun sets over the palace! It’s tempting to eat at one of the restaurants on the square, but beware of tourist traps. We’d recommend moving away a little — you’ll find great little restaurants in the side streets where you can enjoy Siena’s specialities in a much more authentic atmosphere.
You also can’t miss the Palazzo Pubblico and its tall tower that dominate the entire square. The more adventurous can climb to the top of the Torre del Mangia for a spectacular view over the rooftops of Siena and the Tuscan countryside.
The Siena Cathedral is also well worth a visit. Its impressive architecture, black and white marble and richly decorated interior make it one of the most beautiful religious buildings in Tuscany.
We found the cathedral absolutely magnificent! We had been disappointed not to visit the one in Florence, and what a surprise to discover something almost identical! The two cathedrals are indeed very similar. Did you know it’s often said that Siena and Florence have been rivals for centuries, each vying to be the most beautiful city in Tuscany?
We also recommend visiting the interior of the cathedral with its very distinctive architecture, its impressive decorations and above all its incredible mosaic floor — perfectly maintained and without doubt one of the most beautiful we saw during our entire trip.
But as so often in Italy, one of the greatest pleasures is simply getting lost in the alleyways. Siena has an incredible atmosphere, particularly at the end of the day when the golden light illuminates the city’s ochre facades. Between the discreet little squares, archways, narrow passages and numerous traditional restaurants, every walk becomes a real pleasure.
Pienza
This small hilltop village offers absolutely magnificent views over the famous Tuscan hills, the cypress trees and the winding roads you see everywhere on postcards of the region.
The atmosphere here is much calmer and more peaceful than in some of the busier touristy towns of Tuscany, which makes the visit particularly enjoyable. Here, you take the time to stroll through the flower-lined alleyways, admire the sun-drenched stone facades and enjoy the many incredible views over the surrounding countryside.
Pienza is also known for its unique history. The village was entirely redesigned during the Renaissance by Pope Pius II, who wished to create the “ideal city”. The result: everything seems harmoniously organised around pretty squares, elegant buildings and charming little streets.
The heart of the village revolves around the magnificent Piazza Pio II, home to the cathedral, the Piccolomini Palace and several remarkably well-preserved historic buildings. Even though the village is quite small, every street has its own charm and is worth lingering over.
But what struck us most in Pienza were the panoramas. Several small streets open directly onto incredible viewpoints over the Val d’Orcia. At the end of the day, with the golden light of the sun over the hills and fields, the atmosphere becomes almost surreal.
Pienza is also a true paradise for food lovers. The village is particularly famous for its pecorino, a sheep’s milk cheese typical of the region that you’ll find absolutely everywhere in the shops and restaurants. You can easily sample different ageing stages and take home a few local specialities.
Finally, Pienza is also an excellent base from which to explore the magnificent roads of the Val d’Orcia by motorhome or car. The surrounding area is full of iconic Tuscan landscapes and absolutely magnificent small villages to discover along the way.
Montepulciano
Perched at the top of a hill, Montepulciano is one of the most emblematic villages in Tuscany. With its cobbled alleyways, stone palaces, spectacular viewpoints and elegant atmosphere, the village has an undeniable charm and is well worth the detour on a road trip through the region.
From the moment you arrive, you discover a town full of character, built on high ground and surrounded by magnificent landscapes of vineyards and typically Tuscan hills. The climb up the streets can sometimes be a little strenuous, but every turn offers superb panoramas and magnificent old facades that make you want to stop constantly and take photos.
Montepulciano is particularly famous for its celebrated wine: Vino Nobile di Montepulciano, considered one of Italy’s great red wines. You’ll find numerous wine cellars directly in the village, sometimes housed in impressive vaulted underground caves dating back several centuries. Even if you’re not a wine enthusiast, visiting some of the cellars is truly worthwhile just to experience their very special atmosphere.
The heart of the village is Piazza Grande, a superb square surrounded by historic buildings, Renaissance palaces and the Montepulciano cathedral. The atmosphere there is very pleasant, particularly at the end of the day when the terraces start to fill up and the facades take on that beautiful golden colour so typical of Tuscany.
Sanctuary of the Madonna di San Biagio: Not to be missed
Just a few minutes from the centre of Montepulciano stands the magnificent Sanctuary of the Madonna di San Biagio, a place we truly recommend you don’t miss. Set among the hills with cypress trees and the Tuscan countryside all around, this vast church has an absolutely magnificent and very photogenic setting.
Its Renaissance architecture immediately impresses with its great dome and pale stone that contrast perfectly with the surrounding landscapes. Even without visiting the interior, the place is well worth the detour simply to admire the panorama and enjoy the peaceful atmosphere it exudes.
It’s also one of the best-known spots for photographing Montepulciano in the distance with the Tuscan hills as a backdrop. At the end of the day, when the light turns golden, the place is particularly beautiful and offers an almost surreal atmosphere.
Personally, as much as we were impressed by the exterior — very grand — we were far less so by the interior. Once inside, we were actually a little disappointed… The interior is very plain, very empty, almost cold. But as always, that’s just our feeling, and we’d be curious to hear yours!
