Explore the best towns in Tuscany, Italy

Tuscany Italy is like a perfect dream for anyone interested in history, art, culture, food, and wine. With its vineyards, olive trees, and blue sky, it’s no surprise that many people consider it one of the most beautiful regions in Italy. And then there are those picturesque hills with medieval towns and villages on top. Once you’ve visited a few of them, you know why everyone falls in love with these beautiful towns in Tuscany.

When you visit the best towns in Tuscany, you will feel as if time is passing slowly. You will find locals enjoying their time outside, sipping their glasses of Montepulciano red wine and talking to their neighbors for what seems like hours. In other words, you can feel “La Dolce Vita” – the sweet life – everywhere you go, and I’m sure it won’t take you long to realize why Tuscany is one of the most popular tourist destinations in Italy.

You may wonder which are the most beautiful towns in Tuscany?

In this blog article, you will discover which are the best Tuscan towns that you shouldn’t miss. I will be taking you through the key highlights of these must-visit towns in Tuscany, Italy. I will also, recommend the possible places and tours that you can take to explore these Tuscany towns. Consider this post as your first step to building a Tuscany itinerary.

Where is Tuscany located?

Tuscany is a region located in central Italy, on the western coast. It is bordered by the Alpine regions of Liguria to the northwest, Emilia-Romagna to the north, Marche to the northeast, Umbria to the east, and Lazio to the south. The Tyrrhenian Sea forms the region’s western coastline. Tuscany’s capital and largest city is Florence.

History of Tuscany region in Italy

Tuscany has a rich and fascinating history that dates back to ancient times. The region was originally inhabited by the Etruscans, a powerful civilization that flourished in central Italy between the 8th and 3rd centuries BC. The Etruscans left behind a wealth of art, architecture, and cultural traditions that continue to influence Tuscany to this day. From the Etruscans, the region got taken over by the Romans who established the famous towns of Tuscany like Pisa, Siena and Florence.

In the Middle Ages, Tuscany was a collection of independent city-states, each with its own government and culture. The most powerful of these city-states were Florence, Pisa, and Siena, which were known for their wealth, trade, and artistic achievements. During this period, Tuscany became a center of the Italian Renaissance, with artists such as Leonardo da Vinci, Michelangelo, and Botticelli producing some of their greatest works in the region.

In the 16th century, Tuscany was ruled by the powerful Medici family, who were patrons of the arts and played a major role in the political and cultural life of the region. The Medici commissioned some of the most impressive architectural and artistic works in Tuscany, including the Uffizi Gallery in Florence, which houses one of the world’s most important collections of Renaissance art.

In the 19th century, Tuscany became part of the Kingdom of Italy, and its cities and towns began to modernize and industrialize. Despite this, Tuscany retained its cultural and artistic traditions, and today it is renowned as one of the most beautiful and culturally rich regions of Italy

Best towns in Tuscany Italy

Here you can find a selection of smaller and larger towns worth exploring. In fact, when you’re in Tuscany, don’t forget to take it slow and stop wherever you feel like it. Almost all the Tuscan villages and small towns are worth a stroll. It is also, possible to cover some of these towns in Tuscany as a day trip from the bigger ones like Florence. There are numerous tours that you can avail of when you are visiting Tuscany.

That said, it is time we take a look at some of the best Tuscan towns that you shouldn’t miss.

San Gimignano – The Tuscan town of fine towers

While many towns in Tuscany have impressive, medieval towers, San Gimignano offers a spectacular sight already when you’re driving towards it. Fourteen towers characterize the shape of the historic town. Can you believe that it used to be around 70 towers? Each of them belonged to a wealthy family trying to build the largest tower in order to demonstrate their power. It is this particular feature of this medieval town in Tuscany that gives it the sobriquet of the “town of fine towers“.

Torre Grosso is one of the towers that you’re allowed to visit and the view from the top is wonderful. It was built in the 13th century and is considered to be the tallest tower in this beautiful town of Tuscany. You can see all over the town and watch the hilly countryside around San Gimignano. You can grab a combine ticket to this tower along with an entry to the Duomo and various other museums through this link.

The historic center of San Gimignano is a UNESCO World Heritage Site and has many important buildings, including the Collegiate Church of Santa Maria Assunta, which contains frescoes by Benozzo Gozzoli and Taddeo di Bartolo. It also, has the Palazzo del Popolo, which houses a museum of medieval and Renaissance art. You can even opt for one of the many walking tours in San Gimignano to discover these treasures.

The gorgeous Tuscan town is renowned for its golden ham, saffron, and Vernaccia di San Gimignano – a high-quality white wine made from the Vernaccia grape, which thrives on the rugged sandstone hills that encircle the area. You can opt for a wine tasting tour and even go truffle hunting for lunch when you visit this beautiful Tuscan town.

San Gimignano is one of the most popular hill towns in Tuscany. So be prepared to meet many other tourists over there. That’s why you should try to visit during the low season (avoid the summer months July and August) or plan to arrive really early in the morning in case you’re visiting for a day trip.

Curious about a Tuscany road trip itinerary? Check out this post on Jillonjourney.com to get all the tips on what to see besides beautiful towns and how to plan your perfect itinerary.

Suggested places to stay in San Gimignano

• B&B – Le Undici Lune, Coppi
• Hotels – Hotel Bel Soggiorno, Hotel La Cisterna

Siena – one of the most beautiful towns in Tuscany

Another highlight among the beautiful towns in Tuscany is Siena. I haven’t met a person who has visited Siena and didn’t love it. This one has a historic center that was declared as a UNESCO World Heritage Site in 1995 and is truly one of a kind.

Don’t miss Piazza del Campo, Siena’s main square which has quite a unique shape similar to a fan. The central square is also, home to one of the most gorgeous 12th century cathedral called the Duomo di Siena (Siena Cathedral). With its Gothic architecture involving intricate marble facades and ornate interiors, it is considered as one of the most beautiful cathedrals in Italy. The cathedral is home to many notable works of art, including frescoes by Pinturicchio, sculptures by Michelangelo and Donatello, and a spectacular mosaic floor depicting scenes from the Old Testament. Get this Siena Cathedral Complex Pass for a fast-track entry.

For the best view in town, Siena also has a beautiful tower, Torre del Mangia. It’s a tough 400 stairs to climb, but the view is worth it, believe me. You can see the famous Chianti vineyards which are close to Siena, where the popular Chianti wine is grown. Also, you should visit the old University, which was founded in the 13th century and is one of the oldest Universities in Europe.

Besides all these popular sights, one of the most fun things to do in Siena is probably to simply stroll through the historic alleys and get lost. This Tuscany town is full of hidden gems just waiting to be explored among its old brick walls. You can opt for one of these skip-the-line guided tours of Siena. Or you can just download this self-guided audio tour and discover one of the best towns in Tuscany at your pace.

Siena is one of those medievel towns in Tuscany where you can still experience the culture of the by-gone days. Take for example, the unique horse race called Palio di Siena that is held twice in a year. This involves ten bareback riders who are dressed in the heritage Renaissance garb. I believe, these races have been in practice since the medievel times.

Suggested places to stay in Siena

• B&B – Il Barbero, Il Corso
• Hotels – Villa Scacciapensieri Boutique Hotel, Four Points by Sheraton Siena

Vinci – the birthplace of Leonardo da Vinci

The place of birth of the great Leonardo da Vinci is not only worth a visit due to its world-famous artist. For sure, you can’t miss the Leonardo da Vinci Museum in order to get to know his life and works when you’re in Vinci. It’s actually partly located inside a spectacular old castle. From Castello dei Conti Guidi you have an amazing view.

However, Vinci is far more than the famous artist who was given its name. The steep alleyways and historic buildings in town are beautiful as well. You should keep a look out for the Church of Santa Croce, where Leonardo was baptized, and the Casa Natale di Leonardo, a small house that is believed to have been the artist’s birthplace.

Besides, Vinci is located on a slope of the Montalbano hillside, so driving toward this medieval Tuscan town is a highlight by itself. Vinci can be easily done from Florence as a day trip as it is just 40 kms from the Tuscan capital. You can consider booking this tour called The footsteps of Leonardo and a wine tasting tour.

Suggested places to stay in Vinci

• B&B – Le Mimose, Casa Ercoli
• Hotels – Hotel Da Vinci

Montepulciano – one of the best wine towns in Tuscany, Italy

Having the same name as the popular grape variety, you may have an idea of what to expect when visiting Montepulciano. You can find vineyards that offer a wine tasting everywhere around town and on the countryside close by. So don’t miss trying a glass of the spectacular red wine when you’re in Montepulciano. You can also, opt for one of these poular wine-tasting tours.

In addition, this is one of the most picturesque towns in Tuscany. In my opinion, it is especially charming because of its location, a bit off the beaten path in Italy. Settled on a hill in the scenic Val d’Orcia region, Montepulciano is not as crowded as other Tuscan towns. It is definitely one of the best towns to experience the Tuscany countryside.

During your visit you should head to the main square Piazza Grande, the old Cathedral Santa Maria Assunta and of course the old city walls. In case you’re in this Tuscany hill town in August, don’t miss the Bravìo delle Botti, a festival on which locals roll up heavy wine barrels up the hill to Piazza Grande. Quite a unique sight!

Suggested places to stay in Montepulciano

Montepulciano is a part of the Tuscany day trips from Rome, Florence and even, Siena. However, if you want to relax and take in the Tuscan countryside, then here are some places that you can look up for a stay.

• B&B –  L’Agnolo Di Caroti Cinzia
• Hotels – Rondò Boutique Hotel

Lucca – one of the medieval towns in Tuscany

Lucca is well-known for its medieval city walls which are still intact and surround the whole town. So you can walk all around “Mura di Lucca” (or rent a bike to do so) from one ancient gate to another. The well-preserved wall has been designed by Leonardo da Vinci who was born not far from Lucca.

Just as many other beautiful Tuscany towns, you can climb up a panoramic tower in Lucca – Torre Guinigi – which offers a beautiful view across town. From up there you can view the unique main square, Piazza dell’Anfiteatro. It’s oval-shaped because it was built on top of an ancient theater’s ruins. They kept the shape, so you can still get a feeling of how the theater used to look in Roman times.

This quaint Tuscan town is also, called the “city of a hundred churches“. One of the most famous is the Cathedral of St. Martin (Duomo di San Martino), which was built in the 11th century and contains several important works of art, including a wooden crucifix carved by Jacopo della Quercia (an Italian sculptor). Other notable churches in Lucca include the Church of San Michele in Foro, the Church of San Frediano, and the Church of San Giovanni, among others.

Consider taking a guided walking tour of this charming town of Tuscany or try a self-guided bike tour.

Suggested places to stay in Lucca

Lucca is often combined with the other popular Tuscan town – Pisa. If you choose to stay in Lucca (a little less crowded, here are some places with good reviews.

• B&B – Corte Toro, Villa La Tuia
• Hotels – Villa Casanova, Albergo Villa Marta

Bolgheri – a town with the best views in Tuscany

In case you would love a visit to a lesser-known town in Tuscany, head to Bolgheri. The settlement is part of Castagneto Carducci and is surrounded by numerous vineyards. Together with the cypress roads and hills, this gives the town an extremely picturesque location. Some of the cypresses around Bolgheri are said to be there for hundreds of years.

Visiting such a hidden gem like Bolgheri gives you the opportunity to get a feeling for the local life. No cars are allowed inside the historic town, giving you the feeling that time runs more slowly over here and everything looks just like it did in the Middle Ages. You can try local food in an authentic Tuscan tavern without the tourist menus, try wine straight from the local vineyards and visit an old castle without the tourist masses.

That’s simply my kind of place.

Suggested places to stay in Bolgheri

• Hotels – Bolgheri Bramasole

Volterra – a quaint medieval village in Tuscany

Another calm, authentic town in Tuscany is Volterra. Many historic buildings are sprinkled across town, such as the Teatro Romano and the Palazzo dei Priori. If you like diving deeper into history, don’t miss a visit to the Museo Guarnacci, a museum full of historic artifacts and findings from archaeological excavations. 

Arguably the most spectacular monument in Volterra is the Medici fortress (“Fortezza dei Medici”). It looks like it’s watching over the small town and is definitely worth a visit. You can definitely consider a walking tour of Volterra – one of the best villages in Tuscany.

When you’re in Volterra, you will find souvenirs and handicrafts made from alabaster on every corner. For hundreds of years, alabaster has been depleted close by and used as a major material in handicrafts produced in Volterra.

Suggested places to stay in Volterra

• Hotels – Hotel La Locunda

Arezzo – one of the best Tuscan towns for heritage lovers

With its impressive remains of an ancient amphitheater, Arezzo is worth a visit despite its remote location in eastern Tuscany. This 2000-year-old Roman theater is the largest archaeological site in town.

Although Arezzo is lesser-known, it is the fourth largest town (and one of the most prosperous) in Tuscany. So it’s also full of sights worth a visit, such as many piazzas, restaurants, beautiful alleys, viewpoints, and churches. Art fans may want to take a look at the frescoes inside the Basilica of San Francesco, and the crucifix inside the Basilica of San Domenico. An insider tip is to climb up the Cathedral of Arezzo for a spectacular view across the town.

Arezzo is also, well-known for being one of the oldest antique markets in Italy. The market is held on the first Sunday of every month and the preceding Saturday, as well as on the third weekend of every month. You will find a wide range of items, including antique furniture, paintings, ceramics, jewelry, books, and more. Many of the items for sale are several hundred years old and have historical or cultural significance.

In addition to the outdoor market, there are also many antique shops and dealers located throughout the city of Arezzo, making it a destination for antique collectors and enthusiasts year-round. If you are looking to buy, remember to bargain hard.

Two of the most popular things to do in Arezzo are to take a walking tour of this beautiful Tuscan town and the other is to try a local cooking class which is coupled with a market visit and dinner/ lunch.

Suggested places to stay in Arezzo

• B&B – BioBenessere B&B Moto & Bike Parking, Casa Mirko
• Hotels – Hotel Continentale, Vogue Hotel

Pisa – home to the famed Leaning Tower

Home to one of Italy’s most famous sights, Pisa is probably the most visited town in Tuscany. Even in the early morning hours, the square around The Leaning Tower of Pisa starts to become more and more crowded. If you want to take a look at it as well, try to come really early or stay a night in Pisa. In the evening you can get a proper feeling for the town, without its masses of tourists. You should also, try and pick one of these skip-the-line tickets for the Pisa tower.

And Pisa has much more to offer than an unsuccessful building. It starts with the beautiful dome next to the tower. However, the historic center is also worth a stroll. It’s full of beautiful Italian architecture, typical Tuscan alleys, and a beautiful river bank along the Arno river.

Don’t miss stopping by the impressive church Chiesa di Santa Maria della Spina, Palazzo della Carovana, and the National Museum of San Matteo.

Suggested places to stay in Pisa

Given the crowds, I would recommend that you do Pisa as a day trip from Florence.

• B&B – Casa Carducci 33, Five Roses Bed & Breakfast
• Hotels – Hotel Pisa Tower, Hotel Bologna

Florence – the capital of Tuscany

As we’re talking about the best towns in Tuscany, we can’t miss the capital. For many, it’s’ also the perfect starting point for a trip to Tuscany. There’s so much to see in Florence, that you should spend at least a few days here.

It’s Cathedral Santa Maria del Fiore is extremely spectacular and makes up an impressive landmark. And don’t miss the spectacular bridge Ponte Vecchio which is full of colorful houses. The best viewpoint to marvel at the town’s sights from above is undoubtedly Piazzale di Michelangelo. But that’s not a secret, so it gets busy up here.  Eventually, the Uffizi is the place to go to see many of Da Vinci’s artworks (get a skip-the-line pass here)

Suggested places to stay in Florence

You definitely need a place to stay in Florence. Not only exploring Florence will take a few days, but you can also keep it as a base to explore the other beautiful towns in Tuscany, Italy.

• B&B – Residenza D’epoca , Assaporarte
• Hotels – Palazzo Montebello, Sina Villa Medici – Autograph Collection

With that, I conclude my pick of the best Tuscan towns. I hope you have picked your favorite in these. Do drop in a line and let me know which is your preferred town and why.

Common FAQS about Tuscany in Italy

Before you go, pin this

Booking Resources

• Booking.com is a great place to look for stays in Tuscany. They have B&B, holiday homes and hotels in this region listed on their site. You can book them using this link.
• GetYourGuide offers numerous tours, skip-the-line tickets, transfers and day trips for all the towns in Tuscany. You can check the reviews of these offerings and book yours here. Don’t forget to check out specialized classes like cooking classes and the classic wine tasting tours that the site has to offer.
• For any of your travel needs or general shopping, consider using Amazon through this link.

Disclaimer: This article includes affiliate links. This means that at no cost to you, I will receive a small commission if you purchase through my link. Thank you for supporting me with this.

This post has been contributed by my guest author – Jill. She is the author behind Jill on journey, where she writes on sustainable travel, shares inspiration on travel destinations, and provides tips on how to travel more eco-friendly. As she has traveled to more than 50 countries, she has a rich experience of different cultures all over the world. Having family in Italy, she returns there several times every year and has seen many parts of the country. Her mission is to inspire other travelers to see the beauty of this world, so they learn the importance of protecting it.

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