The Most Beautiful Towns and Villages in Tuscany, Italy

Get ready to live the La Dolce Vita life in Tuscany 

Tuscany, in central Italy, is like a dreamland with its rolling hills, vineyards, and quaint villages. It’s a place where the unique beauty makes it an artist’s dream location so I’ve put together my personal favourites into a list of the most beautiful towns and villages in Tuscany just for you!

We travelled to Tuscany this summer for the first time and I don’t mean to sound dramatic but if you haven’t been to Tuscany, you haven’t lived. I can’t believe it took me 35 years to find the secret to happiness – it is sitting on a balcony with a thick book in hand, a wide-brimmed hat, and a flowy off-white linen outfit that looks like it belongs in a Nancy Meyers film, on a lazy afternoon overlooking the Tuscan hills. 

What you will find here

Here you’ll find a list. It is simply all the villages in Tuscany I have been to and which ones I think are best. I haven’t been to every village in Tuscany, yet. Let me know if I’ve missed any that are must-sees in the comment below (or DM me on the gram, like the millennial you are). This is my personal opinion, obviously, so take it or leave it /end of disclaimer.

The most beautiful towns and villages in Tuscany

Siena

Siena is one of the bigger towns in Tuscany and although it comes last in my list, it doesn’t mean I dislike it. It just means I liked the other towns better.

My main issue with this town is that we just happened to go to Siena while there was a festival at Piazza del Campo called the Palio horse race. This is a disgusting tradition where horses are forced to race and often get hurt. There is a parade through the town and many smaller villages from the Siena province come to compete. Apart from the animal cruelty, this town is very pretty.

Monticchiello

Monticchiello is this idyllic hilltop village in Tuscany, Italy. It is one of the smaller towns in Tuscany, which I think is one of its perks. This town was far less busy, and really felt like another world and more authentic than the bigger towns. They also have a community theatre called the Teatro Povero di Monticchiello, which isn’t so aesthetic during the day when it is not set up but I like the idea of it!

Montepulciano

Montepulciano is another larger village, atop a hill overlooking the rolling Tuscan hills. This was actually the last town we visited before leaving Tuscany and it was 100% worth visiting. is famous for its mediaeval charm and many, many wine shops and cellars.  There is also a fortress, Fortezza Medicea, that is worth visiting on the edge of the town.

Florence

Florence, the region’s capital, is a treasure trove of art and history. Florence is a must see when in Tuscany, without a doubt. Whether you appreciate art or not (idk why you’re here tbh if you don’t), Florence will blow you away with the sheer number of beautiful buildings and sculptures that will transport you into a Renaissance wonderland.

If you’re interested in learning more about Florence I have a photo diary of my time in Florence and also my favourite spots for taking photos in Florence.

Bagno Vignoni

Ok, so here is where it gets really interesting. Bagno Vignoni is a rather small, quaint village that is famous for its thermal pool. You can enjoy these down the bottom of the hill, but there is a centuries-old thermal pool right in the centre of the main square, Piazza delle Sorgenti. There are many gorgeous restaurants that line the edge of the square, and this is the perfect spot to spend your evenings in Tuscany. The views from the hilltop are insane, and the atmosphere is just wonderful. 

Pienza

Pienza is famous for a reason, and that’s why it is number two on my list of best towns to visit in Tuscany. If you’re a photographer or influencer, this is the town for you. We got here early and it was still busy, but it was worth it.

This is one of the most well-preserved villages I think I have ever seen, and the quaintness is taken seriously by the locals (every windowsill was lined with flowers and not a cobblestone out of place). This is the best town for views of the Val d’Orcia countryside, near the Cathedral of Santa Maria Assunta.

My Pick: The Most Beautiful Town in Tuscany, San Gimignano

San Gimignano was the first town we went to and none of the others managed to beat it. This is my personal favourite and if you’re only going to visit one, this is the most beautiful towns and villages in Tuscany imo. If you’re interested in authentic, Tuscany culture and history, this is the town for you.

The thing about San Gimignano is that it is exactly what you expect to see when visiting a Tuscan village. It has the history, a 13th century self-contained wall encircling the village, towers looking out across the sprawling hills of Tuscany, and wine, food, and culture that seems almost untouched by the modern day.