Tuscany is full of rolling hills and beautiful towns that range from medieval town life to friendly Tuscan villages and everything in between. There are approximately 270 villages in Tuscany, which means you will have your work cut out for you if you want to experience it all!
The good news is that you can narrow down the list to some of the top Tuscan towns to experience.
In this guide, we share with you the most beautiful Tuscany villages. Whether you’re looking for a hidden gem, a place for wine lovers to hang out, or you just want to experience the medieval buildings and the heritage of an old town or two, there are plenty of small towns and villages to consider.
Check out our picks of the most beautiful villages in Tuscany to add to your itinerary.
The 11 Most Beautiful Towns Across the Tuscan Countryside
Narrowing down the top towns in Tuscany to spend time in is certainly a daunting task. But you can pinpoint some of the famous towns and locations and get to know the must-see spots from Southern Tuscany to Northern Tuscany and everywhere in between.
Take a sneak peek at our top choices for the best villages in Tuscany.
- San Gimignano
- Florence Old Town
1. Cortona in the Rolling Hills
Check out one of the most famous town locations in Cortona. With the Tuscan sun on the horizon of this beautiful hilltop town. Not all hill towns stand out, but this is certainly one that does.
You can experience the historic city center, spend time in the Diocesan Museum, and historic town center of the renaissance village makes this hill town stand out to all.
Travel down the narrow streets of the charming village and breathe in the stunning views of the surrounding countryside of this amazing Tuscan town. From this hill town, you can even spot the city walls and ruins of the old walled town, Etruscan City. Those medieval walls still stand today.
This town in Tuscany was the setting for the novel Under the Tuscan Sun.
One of the must-visit villages of Tuscany stands among the unique villages of choice. This is another Unesco-dedicated site of the small villages in Tuscany, and it’s quite possibly one of the prettiest villages in terms of medieval architecture.
This medieval village hosts a medieval festival every year, as well as hosting a horse race twice a year. The medieval city is known for its buildings, museums, and delicious cuisine as well. The Siena Cathedral is just one historical center of this beautiful village. Make sure you visit the bell tower!
It’s a small town with a big heart and so much history. The historic center of this small town and the town hall are loaded with architecture, history, and stunning art from the Middle Ages.
Right outside the doorstep of Siena lies the Chianti wine region as well.
Another world heritage site in Tuscany, Pienza, is one of the most beautiful villages in Tuscany for a variety of reasons. All the towns in this location have something special to offer. If you’ve ever heard of Pecorino sheep’s milk cheese, this is where it originated from – and it pairs perfectly with local wine!
In addition, you can find a beautiful Romanesque church and several other beautiful churches in the area. This is one of the best towns for modern art and cobbled streets brought together. While you’re in the beautiful town, take in the art and the history and just soak it all in.
Many villages in Tuscany are part of the hilly region, but rather than a hilltop position, this village is surrounded by hills, olive groves, and cypress trees that bring the old town to life in the valley.
4. Volterra Medieval Town
Volterra is another of the small towns with medieval history and characteristics. Volterra remains one of the most beautiful towns of Tuscany villages, and the walls surrounding it seem to just really add to that stunning visual appeal.
Where many of the best towns have a set style or architecture behind them, Volterra is like a melting pot of the region. The village includes art galleries of several different styles and architecture throughout the supports Etruscan, Roman, and Medieval time periods.
And yet, it’s perfectly preserved in every way. This is another village with a famous church, as well as the Roman Theater. It’s a stunning fortress with some of the best shopping in Italy.
Lucca might bring to mind a famous battle from the Renaissance timeframes. This is another walled village, and the original design of the city was all about building a defense. Now, that wall and the internal aspects of the city bring together art, history, culture, and stunning buildings too.
Lucca is one of the Tuscany villages that contains an old amphitheater. The theater is still used for productions today, although the Piazza dell’Anfiteatro now covers most of the original grounds.
Take in an opera, enjoy the summer opera festival, explore museums, and walk through the spectacular gardens.
You won’t find a better visual among Tuscany villages.
6. San Gimignano
San Gimignano is a medieval world history location as well. There are many Tuscan towns recognized by Unesco, and it’s no mystery why. The location is so full of history and architecture, and it’s all been well preserved through the years.
San Gimignano is famous not just for its views. While those are phenomenal, this location is also known for its culinary food. This includes things like tasteful white wine, saffron, and golden ham. The white wine is made from grapes that grow exclusively in the hills surrounding the area.
This town is also known for the 14 towers rather than the main square that people flock to. The towers were always a sign of wealth by patriarch families, and they stand tall and proud today still.
Forget the ruby slippers and head into a quaint village of Tuscany known for ruby red wine. And it is decadent if we do say so ourselves. This is one of the smallest towns in Tuscany that you might visit, so it may be best as a day trip to explore. Despite its small size, it’s still a popular tourist location, so you won’t feel out of place.
Montepulciano is all about the charm. Feel like one of the locals as you take a trip back in town and experience the sights that they have to offer. You will feel like you’re back in history at the locations like Piazza Grande’s main square, the astonishing cathedral, and the tower that gives you views of the entire region.
Many tourists make the trek to the Sanctuary of the Madonna di San Biagio as well. While you can visit by train, it’s a very nice walk, and the views are incredible the whole way. This location also has some impressive caves and underground wine cellars to take in.
Pitigliano is one of the unique towns in Tuscany that stands out in its own way. Set right on the hill, this small village doesn’t have homes and buildings built on the hills but actually built into the hills. The Jewish community has affectionately been named Little Jerusalem because of the close resemblance as well as their Jewish history.
On the hillside, the spots are called tuff. This is where the homes and buildings have been built. You can also travel across the open-air paths of the tuff through Vie Cave. This will be a breathtaking and unforgettable experience.
To this day, they still travel through the caves and tunnels in the tuff, creating their own village inside the hillside. This is one place to experience that can’t be matched by any other nearby stops.
Montalcino is a gracious hilltop village that is the perfect spot for a day trip. They are known for their wines, scenery, and medieval structures throughout the village. If you like wine and art, you will discover tons here to go with that, but it’s also warm and welcoming for those who have no interest in wine.
It’s a lovely little village with historical hotspots and breathtaking views everywhere you turn. The Fortress is perhaps one of the most prominent highlights of the village. It dominates the skyline and makes for an interesting stop to explore as well. The main plaza often hosts events and entertainment for all to enjoy.
Take the time to trek to the highest location in the village and visit Duomo. The panoramic views and historical significance will leave you in awe.
Everything that happens here is family-friendly, and you’re bound to have a wonderful time!
Manciano is another hilltop village that is perched on the edge of perfection. Overlook the hills, enjoy stunning sunrises and sunsets, and walk through the historic village that is packed with buildings, art, and more. It’s a medieval location with pretty visuals and lots of great activities too.
This location is known for the village castle. There are also several storybook castles surrounding the village. From the hills, you can see the Mediterranean Sea and enjoy the life around you. It’s a great place to stay and then day trip to some surrounding areas to enjoy even more.
Bask in the hot springs, enjoy some of the local tours or vineyards, and simply enjoy the sunshine and friendly culture that this village has to offer.
11. Florence Old Town – UNESCO World Heritage Site
Florence Old Town is just one Unesco world heritage site in Italy, and it’s earned the commendation as one of the best locations in Europe. Of the beautiful towns in Tuscany, Florence Old Town will always be a favorite of the beautiful region.
This title refers to the oldest part of Florence, specifically the historic main square location that christens the center of the city and is like a small village within the city. Florence is known for the historical heritage of the village in Tuscany, and it’s a quaint but bustling location.
Perfectly located as the regional capital, you can’t go wrong in one of the prettiest villages of the world. It’s certainly worth visiting Tuscany just to experience the oldest parts of Florence.
Leonardo Da Vinci lived in one of the little villages that is located right around Florence and many of his works can be found in Old Town Florence as well.
The town center, Piazza Grande, and several other tourist attractions make this village section of a popular Italian town a hit as a famous spot you simply won’t be able to overlook.
Planning Your Trip to Villages in Tuscany
These 11 Tuscany villages are just a few great spots to explore. There are many others out there that you can take in and experience. Tuscany is full of beautiful scenery, stunning architecture, and talented artwork. In addition, they have so many winning culinary masterpieces and wine selections that you get the best of everything they have to offer across the region. Tuscany is definitely one of the most famous and visited regions of Italy.
As you’re planning your visits to these Tuscany villages, put a few of these tips to use for planning purposes.
One thing you will want to get settled on is how you will travel from place to place. There are tour options out there that you can choose from, and they often provide transportation. Of course, you can also just use what is available to you. Rent a car, ride the train, or use a bus and local transport option to get where you want to go.
It helps to map it out and break down your travel plans so that you know how to get where you’re going rather than scrambling to figure it out at the last minute.
When to Visit Tuscany
You can visit Tuscany any time of year. Some parts of the year have major crowds, which may impact your planning. Many people from Europe go on holiday in the spring and summer months. This is the busiest peak season. It’s also when the weather is the warmest.
If you want to avoid the crowds and see slightly cooler temperatures, you might consider traveling in the spring or fall instead. However, you may see some cold weather or rainfall in these seasons. Here you can learn more about the seasons in Italy.
Winters in Tuscany are mostly mild, but they are cold and wet. Sometimes they even get some snow there!
Another part of your planning should include accommodations. Where will you stay? Tuscany is home to more than 3 million people and takes up close to 9,000 square miles. It’s no small location. If you want to visit a village on each trip, you will need to do some planning to travel to, through, and around.
Choose one central location to stay and fill in with day trips to nearby villages, or you can hop around and jump from village to village as you go.
Some of the wineries in Tuscany also offer accommodation options.
History, Art, & Scenic Beauty in Tuscany
There are some astounding villages in Tuscany that you absolutely must visit if you have the time. Narrow down the list and prioritize what you want to see the most on your itinerary.
You can’t go wrong with any of the village choices we’ve shared here, and there are many other prime spots that would also be great choices to explore.
Your adventure is waiting! What part of Tuscany and which village will you check out first?
Villages of Tuscany on Map
What is the Most Beautiful Small Town in Tuscany?
Cortona is quite easily one of the most beautiful towns here, but there are many stunning locations.
What is the Nicest Area of Tuscany?
Just about any of the 11 we shared here fall into the nicest areas. Consider places like Cortona, San Gimignano, Montepulciano, Pitigliano, and so many more!
Which is Better: Siena or Lucca?
Both of these locations have great qualities. It simply depends on what you are looking for. Lucca is smaller and not as touristy, so it’s quieter as a whole. Siena is more centralized, which could make a great “home base” for visiting surrounding areas.
Why Do People Love Tuscany?
People love Tuscany for the gentle beauty of the hills, the tasteful food and wine, and the rich history and art throughout the countryside.
What is the Best Town to Stay in Tuscany?
No matter where you choose, you will be impressed. We love some of the accommodations at locations like Cortona, Volterra, Siena, and Arezzo.