The most Picturesque towns in Tuscany

When we booked our trip to Tuscany, I was most excited about ticking off some of its dreamy towns off my list. I had heard and read and seen photos of some of the Tuscan towns that I knew I had to visit them all. Most of the towns and cities we visited could easily feature on my list of the most picturesque towns in Tuscany; however I have done my best to narrow it down. One cannot deny that Italy is beautiful; but my goodness, Tuscany takes it up a few notches.

Tuscany is stupendously beautiful. This side of the Italian countryside is popular for wine tasting, slow travelling and just a relaxing holiday. If you are lucky to stay in the less popular Tuscan towns, you will often meet friendly locals who will make your stay even lovelier.

Where to start from...

For the most picturesque towns in Tuscany, I narrowed it down to a mix of the more popular towns and the underrated and even possibly, unknown ones as well. These 7 towns easily made me want to return to Tuscany. As much as I love historical locations – and Tuscany is the most perfect place for this – I absolutely love a pretty location as well.

What you see – The bountiful cypress trees which adorn the roads as you drive by, epic sunsets and sunrises, most stunning countryside landscape and dated architecture make Tuscany one of the prettiest destinations I have ever seen. The farmhouses date as far back as the 14th century and just driving around, you pass by different Agriturismos*.

Related Post: A Family-Friendly Travel Guide to Tuscany

Murlo

Oh Murlo was a dream to stay in. It is the most unassuming, tiny village, which charmed and welcomed us all. When Mr E booked the villa we actually had no idea what part of Tuscany it was. All we did was check distance to the airport and figured we’d explore when we got there. This is where I admit I’m glad we got hit with the element of surprise. Murlo is stunning! The perfect base for our huge family that was as family friendly as it was romantic. Although we spent a lot of our afternoons visiting nearby towns, our evenings were for walks around Murlo. The kids were excited to use the 2 playgrounds we often walked past and the gelato café became our regular pit stop.

Murlo is a commune and the population resides in Vescovado and Casciano. We were based in Vescovado, which is home to the municipal house. Murlo is one of the most ancient settlements in Tuscany. Its hill of Poggio Civitate is currently the site of archeological investigations. The village has Etruscan origins and the relics that are being investigated which suggest that the Etruscans may have come from Murlo.

Another location worth a visit is the 12th century Castle of Murlo.

Pienza

This one totally stole my heart. Pienza is located in the historical region of Val d’Orcia and is right in between Montepulciano and Montalcino. It is often described as the “ideal city of the Renaissance” and has been recognised as a UNESCO heritage site since 1996. Although it is relatively a hidden gem, it is quite popular with movie productions. I recently watched Medici after I read that Tuscany had been used in production. I was so excited to see Pienza featured a lot throughout the seasons.

Pienza is named after Pope Pius who was born there in 1405.

I must admit that Pienza was my favourite of all the towns we visited. It was slow, incredibly scenic and so romantic. As we walked from the car park to the center, we heard an opera singer belting out some classics. It felt like we were in a fairytale as we walked towards the music.

The main thing that actually drew me to Pienza was the Pienza Cathedral aka Duomo di Santa Maria Asunta. It is right in the center and we walked in to have a little peek. The Cathedral was built in the 15thcentury in Gothic and Renaissance architecture. It truly is one of those structures that just draws you in. We walked around and spotted so many pretty little streets and friendly locals.

Things not to miss in Pienza:

Pienza Cathedral (Duomo di Santa Maria Asunta)
Il Cipressi– a picturesque farmhouse
Palazzo Piccolomini by Rossellino
Pieve di Corsgnano

Pienza - Il Cipressi

We stumbled upon il Cipressi on our way out of Pienza. I had no idea it was a part of Pienza until I did a bit more research. One day, I will stop gushing about Tuscany but today is clearly not the day. This spot literally left me in awe. Il Cipressi is on the outskirts of Pienza, on the way to Montalcino. It is very easy to miss but my word, one of the best sights I have ever seen.

Our wander ended with a late lunch in a stunning al fresco restaurant, Trattoria Latte di Luna. We had some pasta, chicken and lots of aperol spritz. I really cannot put into words how special Pienza was but if there is one place I’d go back to, in Tuscany, in a heartbeat, it is 100% Pienza. My sprit was so in tune with it and I could tell that Adanna absolutely loved it too. For me, Pienza was magical and romantic and felt like I was in a Disney movie the whole time we spent there.

Siena

Technically, Siena is a city but for the purpose of this post, it falls under this topic. I don’t think it is possible to go to Tuscany and not visit Siena as it is quite nearby. Siena is one of the most picturesque towns to visit in Tuscany. Mostly because it is quite different from the typical countryside vibes that other Tuscan towns have to offer. Siena is more city than it is village and boasts of the most incredible medieval architecture.

We drove from Murlo to Siena in about 35 minutes and parked at the city’s car park. One thing we quickly noticed was that it was not the most family friendly town to navigate especially with a stroller. It reminds me of a smaller and less boisterous Rome. This ancient medieval city packs a punch and our 1st stop was of course, its popular Duomo. A visit to the Duomo set the tone for the rest of our day trip to Siena.

In all the busy-ness, we often found picturesque alleys off the major streets to wander and experience the beauty of this preserved town. Washing hanging from lines, flowers adorning windowsills and foliage creeping around doors made us feel like we were in an Italian movie. From the Duomo, we headed to the Piazza del Compo, which I had read so much about. It is regarded as one of Europe’s greatest medieval squares so it was special to see in all its glory.

Montepulciano

We visited Montepulciano on a sunny afternoon and it did not disappoint. I had read that it was the town for wine tasting so we were chuffed to find a wine tasting bar that was baby friendly! Podere Cassanova is located right in the heart of Montepulciano town center and we were greeted by its kind sommelier as we walked in. For €20 per person, we tasted 3 wines from the region and although I am not a fan of red wine, it was a lovely experience.

Most of the afternoon was spent walking around the pretty town, discovering hidden spots and taking it all in. We had about 2 hours to explore and we felt like we saw enough of this pretty town. Montepulciano is like any other Tuscan town but the stand out for me was the view from the hilltop where we parked our car. It felt like we were looking at all of the Tuscan countryside. In the distance, rolling hills, farm lands and of course cypress trees greeted our sights. The whole thing felt like an oil painting. We located a viewpoint which literally looked like a window to the world LOL; dramatic? I know. But from that little “window” we had the most stunning view of the Tuscan hills.

We walked up the hill to its Piazza and sat by the medieval wall. It was the perfect place to sit while Adanna ran around and we people watched. Just across the well is the Duomo and to its right is a pretty outdoor café. The whole time we were there, it felt like I was in a movie set. I guess it is not surprising seeing that Twilight, Under the Tuscan Sun, Medici and a few other classics were filmed in this pretty town.

San Quirico d’Orcia

This might be the most gorgeous of all the towns we visited. Home to the famous Poggio Covili farmhouse; San Quirico d’Orcia is in a world of its own. If you are looking for the most settlement of the iconic cypress trees – yes the ones Tuscany is known for – you will find them here. It is also a very famous location from the Gladiator movie.

We got there mid afternoon and had it all to ourselves. It felt like we were walking up to our own farmhouse.

The initial plan was to visit Agriturismo Poggio Covili for photos but we were too mesmerised to leave. We ended up driving around and spotting as many cypress trees as possible. After driving around, I think Poggio Covili has the most impressive scenery of them all. This is where I should mention that Poggio Covili is actually a farmhouse available to stay.

San Quirico d’Orcia borders Montalcino and Pienza. Aside from Poggio Covili, there are a few other locations worth a visit especially the religious architectures. One worth a mention is the Collegiate Church of Saints Quirico and Giulitta, which is the main parish church of the town.

San Gimignano

San Gimignano is actually one of the most picturesque towns to visit in Tuscany and is close to Siena. It is known as the town of Fine Towers as there are more medieval towers in San Gimignano than in other Tuscan towns. History has it that wealthy merchants built these towers to display their wealth and power; however, natural disasters and wars have brought them down.

San Gimignano is a tiny, medieval hill town known for its architecture and stunning skyline. Its architecture is medieval and the town itself is walled as with a lot of the Tuscan towns we visited. The centre is a UNESCO heritage site as well; which makes sense considering the architecture dates back to the 14th century. Its well preserved buildings are examples of both gothic and Romanesque architecture especially the churches.

For our trip to San Gimignano, we did not cover the whole town but were there for something special. Our trip to this medieval town was to visit the most beautiful vineyard in the Tenuta Torciano estate. Exploring the Torciano winery was such a delightful experience that made our Tuscany trip a million times better.

Aside from pretty vineyards thanks to its Vernaccia grapes, San Gimignano is known for cheese, saffron and ham.

Bagno Vignoni

Bagno Vignoni is another one of the most picturesque towns in Tuscany. It is popular for its thermal bath, which sits in the main piazza. The waters reach a temperature of up to 52 degrees, which makes it the hottest thermal bath in Tuscany. It is such a fascinating little town. Every other town would usually have a Church sat at its center but not Bagno Vignoni. It’s a shame that visitors can no longer bath in the pool; however it is lovely enough to visit and marvel (and of course take photos) of the giant stone bath that is surrounded by stone houses.

The history dates back to the 9th century as mentioned in old travel journals.

It sits just outside San Quirico d’Orcia (some would argue it sits within) and is on the edge of Parco della Val d’Orcia. Bagno Vignoni is only a few minutes from Via Francigena. For history and theology lovers, Via Francigena is one of the most important travel routes in history. It would have been the route taken by pilgrims from England to the Holy Land. Therefore, it is believed that the Romans and Etruscans would have used the hot springs in Bagno Vignoni, for both medical and cleanliness purposes.

Aside from attracting people to view its thermal bath, Bagno Vignoni is also a working mill town.

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The most Picturesque towns in Tuscany - my thoughts

The most picturesque towns in Tuscany go on and on. Depending on how long your trip to Tuscany is, there are so many more you cold visit. I had Montalcino on my list but we ended up sleeping in that morning and taking it off the list, which is a shame as it was quite close by. This might be a reason to return to Tuscany. I know I will go back at some point. Tuscany is not a one-time visit kind of location. It is too beautiful and full of history not to experience even more of it. We spent 10 days there, slow travelling and enjoying the summer sun and it still was not enough.

Cheers to pretty countryside locations, the most picturesque towns in Tuscany and all the beauty this world has to offer.

Until my next picturesque travels….

…Bisous, Bugo x

*An Agriturismo is a farm that has been designed to receive guests. This could be for lunch and dinner and/or holiday accommodation. The word “agriturismo” is a combination of agricoltura, which means agriculture, and turismo, which stands for tourism. In these beautiful farms, you are able to eat local produce direct from the farms; some offer cooking classes, horse riding and truffle hunting