What do you associate Tuscany with? Most likely with idyllic, rural landscape, with wine and fairy tale like medieval towns and villages. Because of that we have created subjective list of 14 the most beautiful towns in Tuscany which we share with you below!
Florence – 14 most beautiful towns in Tuscany
Florence isn’t a town really, rather a city but exclusion of the Tuscan pearl in this post would be an insult so here it is. We spent only one day in Florence and definitely this isn’t enough. The first records of Florence speak of a small settlement founded by the Etruscans in the 18th or 19th century BC, which was destroyed in the 1st century BC. After several years, it was rebuilt by the Romans as … a colony for former soldiers.
The name of the city evolved over the years, and finally came to the current form – Firenze. In the nineteenth century, Florence was the capital of Italy for just 6 years. It’s also believed that the Renaissance was born in Florence, and Renaissance architecture can be found there at every step. What we cherish in our memory the most about Florence is the Cathedral of Our Lady of Flowers (Cattedrale di Santa Maria del Fiore) and the view from the Piazzale Michaelangelo viewpoint. You can find more about how we spent one day in Florence here.
Siena – 14 most beautiful towns in Tuscany
Siena is also a place which should be described as a city, not a town, but we decided to include it in this post together with Florence. If you plan to visit both places – we recommend reaching Siena first, and then Florence. It’s the best way to dose the emotions, Siena provides a lot and Florence even more.
We started our trip by leaving the car in the parking lot and thus discovering a great viewpoint over the city – the parking lot is called Il Campo and you need to take the elevator to the very top, and then exit the building, you go to the city along the city walls with a beautiful view (parking is marked on the map at the end of the post).
A must-see is of course the Piazza del Duomo, the square next to the Duomo di Siena cathedral. We walked leisurely along Via del Capitano, the cathedral slowly looming on the horizon – when we saw it in its full splendor, we couldn’t believe our eyes. It’s one of the most beautiful buildings we have ever seen! We went inside for free and without queuing, but it’s only because we came during the coronavirus, normally the entrance is paid and it takes some time to get inside. However, it’s worth spending every penny there! The interior of the cathedral is as electrifying as its facade. We would compare it to seeing the Sistine Chapel in the Vatican in relation to experienced emotions.
Another important place in Siena is Piazza del Campo, which is a huge square that can be called a market, next to which there is the Palazzo Pubblico town hall and the famous tower Torre del Mangia. While in Siena, it’s also worth taking a walk along the main shopping street – Via Banchi di Sopra.
Montepulciano – 14 most beautiful towns in Tuscany
Like most of the 14 most beautiful villages and towns in Tuscany, Montepulciano is situated on a hill, surrounded from every side by endless stretches of vineyards and fields. We started our adventure in Montepulciano the best possible way – with Vino Nobile di Montepulciano, which we drank by the swimming pool in our agritourismo, staring at old town buildings being illuminated by sun setting behind them.
We booked the night in the agritourismo Godiolo, which has a spectacular view of Montepulciano rising on the hill. We started our sightseeing first thing in the morning, when the town was still asleep and not even a single soul we met on its streets. In Montepulciano, the obligatory point is Piazza Grande, i.e. the monumental square where the film Twilight was filmed. When wandering around the town, it’s worth finding a place with a view of the Chiesa di San Biagio church which is really impressive!
Montalcino – 14 most beautiful towns in Tuscany
Both Montalcino and Montepulciano are associated with a bit of luxury and splendor, mainly due to fact they produce some of the best Italian wines, and the best usually means expensive. Of the two mentioned, in our opinion Montalcino has a more exclusive atmosphere. Although we like Montepulciano more, Montalcino definitely wins with views of the surrounding Val d’Orcia valley full of vineyards and fields.
While walking around Montalcino, you will definitely not miss the main square, Piazza del Poppolo. Nonetheless one not should be intimidated to visit. Best way to experience Montalcino is by getting lost in its charming streets. There is a few places with affordable food and drinks as well.
Pienza – 14 most beautiful towns in Tuscany
The little Pienza is located in the middle of the picturesque Val d’Orcia. The views from Pienza are truly amazing as well as town itself which made it to the UNESCO list in 1996. The historical part of Pienza isn’t very big, but it’s teeming with life. On the main street there are shops selling local cheese and ham one of them famous Pecorino di Pienza which guess what… is produced in Pienza.
Pitigliano – 14 most beautiful towns in Tuscany
Pitigliano is called the city of tuff, and tuff is a volcanic sedimentary rock. These rocks are easily eroded, so Pitigliano slowly crumbles (although it doesn’t look like that at all). We spent the night in Pitigliano, we chose AirBnb located in cave with a perfect view of the town. We sat with the door open all evening, drinking wine and staring at Pigitliano.
Late in the evening we decided to explore the streets of Pitigliano. We discovered a square with lively restaurants, there must be a beautiful view during the day – at night the area around Pitigliano is pitch black because the town is surrounded by fields. In the 15th century, Jews who were fleeing the Counter-Reformation from Rome settled there in Pitigliano. During World War II, they miraculously escaped capture, but today only an abandoned synagogue remains of the Jewish community in Pitigliano. Pitigliano is a great base if you plan to go to Terme di Saturnia early in the morning, it’s only 30 minute drive to the thermal baths.
Radicofani – 14 most beautiful towns in Tuscany
Radicofani is a town with a fortress towering over it. The whole mountain is visible from a distance and it looks very intriguing. It’s precisely because of the very interesting location Radicofani was included in our list. The tower is the main attraction.
Asciano – 14 most beautiful towns in Tuscany
We got to Asciano before noon, the town at this time without tourists, had a life of its own. The kids were racing around the streets on their bicycles, completely ignoring the passing people, and the old ladies looking out of the windows, checking what was happening in the neighborhood. Pastel tenement houses charmed us so much that we stopped in one of the cafes for a glass of wine and for several dozen minutes we watched life in Asciano. Such unplanned, clam and true moments which we enjoyed without haste, are definitely the best memories of Tuscany!
Monteriggioni – 14 most beautiful towns in Tuscany
Monteriggioni is a village that will take up to 15 minutes to visit, but it’s worth allocating it! Monteriggioni is a tiny settlement located on a hill, surrounded by walls with 14 towers. Of course, it looks most spectacular from above, but the village itself and its atmosphere are very pleasant. The main point is Piazza Roma square, where restaurants set up their tables. Time passes slowly, and with a glass of wine you can spend much more time there than the aforementioned 15 minutes. The whole place looks like one big open air museum or film setting.
Volterra – 14 most beautiful towns in Tuscany
Voleterra is a town founded all the way back by the Etruscans, because of the alabaster mining and processing it there, it’s called “the city of alabaster”. Part of the action of the book and film Twilight is taking place in Volterra, it was inhabited by the Volturi. Interestingly, the film Twilight was shot not in Volterra, but in Montepulciano. In Volterra, we didn’t skip Piazza dei Priori square, but apart from it there was no detailed plan. We regret the beautiful Teatro Persio Flacco was unfortunately closed due to the virus. There are also ruins of a Roman amphitheater in Volterra, which we skipped this time- we visited two such places in Syracuse and Taormina, and in Tuscany we wanted to spend time on other things.
San Gimignano – 14 most beautiful towns in Tuscany
We arrived in San Gimignano in the early morning, when the cafes were just opening and the inhabitants were taking their pets for a walk. When reaching San Gimignano, a medieval towers appears on the horizon – there are only 14 of them now, but in the past there were many more. Torre Grossa is the highest of them, measures 54 meters and is part of the Palazzo Nuovo del Podesta, i.e. the new town hall.
Subsequent towers, according to the applicable law, couldn’t be higher than the tower of the town hall, they were built on private orders. The towers were of course a defensive element of the town, but the height of the tower indicated the wealth of the family that ordered its construction. The towers of San Gimignano have been compared to the skyscrapers of New York and this is how San Gimignano gained the nickname “Medieval Manhattan”. The town made a really positive impression on us and we highly recommend it.
Lucca – 14 most beautiful towns in Tuscany
The circular Piazza dell’Anfiteatro square, built on the remains of the Roman amphitheater, is one of the places most often appearing on postcards from Tuscany. It was this square that brought us to Lucca and we almost missed it… The entrance to the square is narrow and it’s located in a side street, we made 5 rounds around the town to finally get there. We have to admit that Piazza dell’Anfiteatro from the sidewalk level doesn’t make such an impression as from the air.
It must be admitted that Lucca is a very pleasant town to hang around. You must see the Piazza Michele square with the church of Chiesa di San Michele in Foro. Another place worth seeing is the Duomo di San Martino cathedral. Lucca is also a great place for shopping, we probably haven’t seen so many atmospheric, beautifully decorated shops anywhere, with literally everything – from food, through clothes, to books and antiques!
Pisa – 14 most beautiful towns in Tuscany
Another city on our list… we should probably call it villages, towns and cities of Tuscany.. 😉 If we are to be completely honest with you – Pisa wasn’t such a hype as it’s normally described. The old town isn’t too big, you cannot deny its charm, but it’s also not very thrilling. The streets of Pisa are much wider than those characteristic narrow streets in Tuscan towns situated on the hills.
Pisa is located on a completely flat area, and the cathedral Cattedrale di Santa Maria Assunta a Pisa and the leaning tower are visible from a considerable distance. One must admit – the square Piazza del Duomo with the tower, cathedral and San Giovanni Baptistery makes a really electrifying impression. We bet, however, that with the usual crowds that normally gathers in the square, the feelings may be slightly different.
Sorano -14 most beautiful towns in Tuscany
Sorano, Pitigliano and Savona belong to the three towns on Tufa. The most famous is Pitigliano, which we wrote about above, we didn’t reach Savona, and we only admired Sorano from a distance. Whatever the case, the view of Sorano from the road was really great. A castle built in the 14th century towers over the town, and brick houses crowd the hill creating a picturesque landscape.