When most people think about Tuscany, they think about Florence, which is an incredible city. Don’t get me wrong. But what if I showed you some of the most charming small towns and villages that you didn’t know existed in Tuscany?

These towns are where you will find the true heart of this enchanting region in Italy. With rolling hills, vineyards, and charming villages creating a picture-perfect landscape. From ancient hilltop villages to charming medieval towns, each one offers its own unique charm, breathtaking views, and local delights. In this video, I’m going to take you through 10 of the most charming towns in Tuscany that are sure to steal your heart. Are you ready? Let’s get started.

San Jimnyano

First up, we have San Jimnyano. Often referred to as the town of fine towers, this is easily one of the most picturesque towns in Tuscany. And I wanted to start off strong with one of my favorites. San Juano is known for its 14 medieval towers that rise above the town skyline and make for a great day trip from Florence. Now, I’m going to link a few of my favorite day trips from Florence that cover some of these towns, including this one, in the description below. What makes San Jimnyano so special isn’t just its towers, though.

It’s that the town is a UNESCO World Heritage site and offers a wonderful mix of history, art, and food. It’s also famous for its vernacy and is considered one of the best white wines in Italy. The town’s cobblestone streets are lined with charming shops, restaurants, and cafes, making it a great place to wander and soak in the beauty of Tuscany.

San Quirico Dior

Next up, we have San Quirico Dior, which is a charming, lesserknown gem located in the heart of Tuskany’s Vald Dior region. Now, I’m going to be honest. I do not speak Italian, so this is my best attempt at the pronunciation, and I do apologize in advance. When I’m visiting, I usually like to stay in the Valdi Orche area because it is so pretty, and I love being close to all the nature. While it may not be as famous as some of its larger neighbors, this quaint village offers an authentic and peaceful experience of the Tuscan countryside, which keeps me coming back to this specific area. San Quo de Orchia is not only a town steeped in history, but also offers some of the most magnificent views in Tuscany. It is perched on a hilltop and the village is overlooking the rolling hills below, which are actually a UNESCO World Heritage landscape. The views here are perfect for those looking to capture the quintessential Tuscan landscape in all of its glory.

Voltater

Number three is Voltater, a captivating town that blends rich history and medieval charm. Now, Voltater sits high on a hill, offering panoramic views of the surrounding Tuscan countryside. I am totally obsessed with this town. It is just so cute. It is famous for its alabaster and you’ll find many local artisans who create beautiful sculptures and jewelry from this soft white stone.

Volterra also has a Roman theater which is perfect for history buffs looking to learn more about the town’s ancient past. The winding streets, charming shops, and incredible views make Volta a must visit for anyone traveling through Tuscany.

Monte Pulchano

Next up is Monte Pulchano. And if I had to pick just one Tuskanyany town located on a hilltop that I am totally in love with, it would be this one. I feel like this town perfectly captures the essence of Tuscany while at the same time offering visitors an authentic taste of Tuscan life. It isn’t called the jewel of Tuscany for no reason. The town is perched high on a ridge, providing sweeping vistas of the surrounding valleys and hills, making it one of the most beautiful spots in the region.

Monte Pulchano is famous for its Renaissance architecture with elegant palaces, churches, and piazas that are perfect for a leisurely stroll. But the real draw here is the wine. And it is home to one of the most renowned red wines in all of Italy. I’m going to drop a wine tasting tour in the description if you’re looking for recommendations while visiting here. I highly recommend visiting Monte Pulchano. It is truly one of the cutest small towns right here in Tuscany.

Luca

Number five is Luca, a town that is perfect for strolling and taking it slow. Now, Luca is known for its wellpreserved Renaissance walls. And what makes this town special is that the walls have been transformed into a park where locals walk, cycle, and relax.

Inside the walls, you will find charming piazas, beautiful churches, and cobbled streets lined with shops and cafes. Luca is also known for its music festivals.

So, if you’re lucky, you might catch a concert or performance while you’re in this adorable small town.

Sienna

Up next is Sienna, one of Tuscan’s most famous towns outside of Florence, and for a good reason. Now, this town is known for its medieval architecture and vibrant history, and it really feels alive with the past when you visit.

Sienna makes an incredible and super easy day trip from Florence, and I’m going to drop my suggested tour in the description. The main square in Sienna is one of the most famous and beautiful in all of Italy. The Sienna Cathedral is another must-see with its stunning black and white striped facade and intricate interior.

I truly believe that Sienna is one of the best destinations in Tuscany because it perfectly combines history, art, and architecture, and it’s a super easy day trip from Florence.

Sorrano

Number seven is the charming village of Sorrano. Now, it has been a few minutes since we’ve covered a cute hilltop town in Tuscany. Aren’t you missing it? And Sorrano is just that. It is dramatically located on a steep hilltop and it is a total hidden gem that offers a glimpse into Tuscan’s ancient past. The town’s medieval fortress and the labyrinth of narrow streets will transport you back in time.

I also love the surrounding countryside. It is stunning with beautiful green hills.

Sorrano is truly the perfect destination for both nature lovers and history buffs to enjoy this cute hilltop village in Tuscany. Next up we have Pienza, a town that is so perfect that it was declared a UNESCO World Heritage site.

Pienza

Are you sensing a theme here? The towns in Tuscany are so incredible that there are many UNESCO designations in this region. Pienza is often referred to as the ideal Renaissance town thanks to its carefully planned streets and squares. The town is also famous for its pecarino cheese. So you will for sure want to stop at a local shop or restaurant so you can give it a try.

Now, Pienza is another town located in my favorite part of Tuskany, which is Vald Dior Orchae. As I mentioned earlier in this video, when you visit, you will be treated to some of the prettiest landscapes in all of [Music] Italy. Number nine is Petiliano, which I personally think is one of the most epic cliffside towns in all of Tuscany. It is dramatically located on a cliff and the town looks like it was carved straight into the rock, giving it a unique and almost magical feel. This place is absolutely incredible and a must visit, especially if you are specifically interested in hilltop towns like me. Now, walking through Pitiliano’s narrow and winding streets, really does feel like stepping back in time, and the views of the surrounding countryside, especially at sunset, are absolutely spectacular. The food here is also really good, and I really do think that this town is a total hidden gem in Tuscany.

Monttocchino

Finally, we have Monttocchino. Located among the rolling hills of Vald Diora, my favorite area, this town is also home to one of the most famous red wines in the entire world called Brunello Deontchino. If you are a wine lover, this is a great town to visit because there are lots of places and local wineries nearby and many areas where you can do wine tastings. The town itself is full of charming medieval streets, historic buildings, and has an all-around welcoming atmosphere. There’s even a 14th century fortress that you can tour here. And it is one of the most iconic features in the city. If you’re looking for an incredible red wine blended with a beautiful picturesque location and ancient streets, Montalcino is the perfect place to explore.

Tuskanany is a region full of hidden gems, and these small towns and villages are just the beginning. From medieval streets and ancient architecture to stunning views and delicious food, there’s something for everyone in Tuscany. So, if you’re planning a trip to Italy, make sure to add these charming towns to your itinerary. Even if you’re just going to Florence and making it your home base, there are still plenty of cute small towns that make super easy day trips. I hope that this video has inspired you to visit some of the most beautiful and charming towns in Tuscany. Don’t forget to like, subscribe, and hit that notification bell.