Pretty towns & villages in Tuscany to visit!

A visit to Tuscany is a definite bucket list item.  Tuscany has many pretty towns and villages to discover.   In my previous post, I covered Florence, Lucca and Siena which we used as our base and where we hired a car to explore the many towns and villages.   In this post, these are the places we visited and I would recommend.

Central Tuscany


This tiny village is well worth a small detour. A small journey from Siena and it was our first village after picking up the hire car.  It is quickly seen and is just delightful.

It is a walled village and has a little church and a main square, the Piazza Roma and one single street.  It was founded in 1203 to act as a defensive bastion against the Florentines approaching Siena.  We had a lovely relaxing pit stop sitting in the outdoor cafe having coffee and pistachio cake.

We had decided that we were going to buy at least one bottle of wine from each village and town we visited, so after a lovely walk around this tiny place, we went into one of the wine shops to buy some wine and pecorino cheese.

San Gimignano

San Gimignano is what you would picture how a medieval Italian village should look like. It is set on a beautiful hilltop setting, like many of the villages and towns we visited.

The village is small, about ½ mile end to end.

Again a pleasure to stroll around and we had a really tasty pizza in one of the outdoor restaurants.


Another charming medieval town, high up on a hill surrounded by city walls.  Volterra is one of the oldest towns in Tuscany and has one of the best preserved centres in Italy.  The main square Piazza dei Priori is one of the most impressive in Tuscany.

Southern Tuscany


Pienza  is a UNESCO World Heritage Site and a wonderful example of Renaissance Architecture.  It means City of Pius, named after Pope Pius II, who was born here.  It is about 50km from Siena, set in a beautiful natural landscape of olive groves and pretty villas.  Approaching Pienza, you have beautiful views all around you.


There are small shops along the streets selling local handmade goods, food and wines.

This was one of hubby’s favourites, another pretty medieval town.  Set amid a beautiful hilltop setting.  It was also used as a film location for the film Under the Tuscan sun.  We found Cortona to be really relaxing and it was lovely wandering around the streets.


This is where the wonderful Brunello Wine is made. Montalcino is another fairytale hillside village in the beautiful Val D’Orsia national park, which is a UNESCO protected world heritage site.  Like all the Tuscan towns and villages we visited the shops have lots of pottery, paintings and Tuscan ornaments.  Everywhere we went in Tuscany, especially these small towns and villages, the people were friendly and helpful.

The town is watched over by a large fortress which has remained practically intact since the middle Ages.

We wandered in and discovered a huge courtyard with a very large wine shop. They also do wine-tasting and needless to say, we felt it would be rude not to partake! The Brunello wines were simply gorgeous. So gorgeous we had a fabulous lunch of antipasti, plenty of breads, cheeses, meats & olives accompanied with a couple of different wines. The whole afternoon was amazing and so relaxing. The fortress itself is often used for festivals and concerts such as the Jazz & Wine Festival which takes place in July each year.

Abbazia di Monte Oliveto Maggiore

A Benedictine abbey situated not too far from Siena. What struck me was how peaceful it was.

There are beautiful frescoes painted all over the walls and ceilings.  You can wander around the Abbey and its beautiful grounds.  There are monks silently reading or praying, so we tried not to disturb them.

You can see where they eat in a large dining hall, the table set very simply.  The Abbey is isolated and is a tranquil place.


This was on my list of towns I had to see as it had been recommended to me. It did not disappoint, it’s a delight to explore and is very pretty.

The Cantina Ercolani is a wine shop located in the centre of Montepulciano, but what a surprise we got when we entered!

There is an underground, historical wine cellar that they have turned into a museum.

Many of these Tuscan towns have large tunnels, like city lanes underground where people secretly met to plan and plot dastardly deeds.  Part of the Museum has a part dedicated to a torture chamber and there are lots of ancient torture devices in the museum.  After the tour, we came back up to the shop, where we got free wine-tasting and lovely free samples of breads and cheese.  Needless to say we bought a couple of bottles of wine here.

We spent a fabulous day in this town, exploring, visiting the shops, strolling about at our leisure, eating and of course wine-tasting.

One of the shops we strolled into, the owner was very enthusiastic! He brought us around the whole of his shop, out the back to show us his inventions.  He was also a talented artist and hubby had been looking out for a painting he would like of the Tuscan countryside and here in this shop I got it for his birthday.  The colours are just gorgeous!  You would mostly associate lavender fields with France, but here in Tuscany there are some Lavender farms.

Most of these pretty villages and towns are on a hilltop setting and most still have parts of the old city walls surrounding them.  You can buy really good local wines and produce and lovely pottery and handmade gifts.

A trip to Tuscany is a definite must see!

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