Are you wondering what towns in Tuscany you should include in your Italian itinerary? I have been around the Tuscany region. Each town has its own character and charm. I highly encourage you to visit as much as possible to experience the Tuscan adventure.

The region known as Tuscany exudes an air of enchantment that permeates the entire region; from the buildings to the countryside, everything is captivating and alluring in equal measure. There are indeed a lot of things to do in Tuscany. Now, it can be difficult to decide which typical towns and villages in Tuscany to visit on vacation, especially if you want to avoid tourist traps and see more of the authentic side of the region.

Driving around in a car is the most efficient way to explore. It is a revelation to drive around this gorgeous region, and it is a great way to see as much as possible from your villa in Tuscany. To give you a true taste of ‘la vita Italiana,’ here’s compiled a list of some of Tuscany’s most picturesque and historically significant towns and villages. The past of the Middle Ages, walled towns, and the aesthetics of the Renaissance are in store for you.

Read More: 8 Best Things to Do in Tuscany Region, Italy

Here are the pretty towns in Tuscany:

1. Florence

Over the course of its history, Florence has been able to captivate the imagination of its guests. The historic center of this city, which serves as the regional capital of Tuscany, was inscribed as a UNESCO World Heritage Site in 1982. 

Beautiful Towns in Tuscany: Florence

Florence is often cited as the city where the Renaissance first appeared in Europe, and for good reason. During that time period, Florence was the birthplace of many famous artists, including Michelangelo, Botticelli, and Leonardo da Vinci. This once-great city has maintained its status as a global leader thanks in large part to the art and architecture of its heyday. The Duomo is one of the most beautiful churches in Florence, and probably one of the most iconic churches in Italy. 

Palazzo Pitti and the Uffizi Gallery are just two of many Florence’s art galleries and museums that can be found in Florence, which continues to maintain its status as one of the most culturally significant cities in the world. You will be able to shop for one-of-a-kind artisan goods, dine elegantly, and fully immerse yourself in the authentic spirit of the Renaissance here. You could also just take a stroll along the Arno and take in all the splendor that surrounds you.

There are great things to do in Florence. That is why most travelers ranked Florence as the best city in Europe, and they cited the city’s extensive artistic and architectural heritage as the reason.

2. Pisa

Pisa is one of the most well-known tourist destinations in all of Tuscany, and its most famous attraction is the Tower of Pisa. However, there are more things to do in Pisa and more to discover in this fascinating city.

Pisa Italy
Beautiful Towns in Tuscany: Pisa

A significant number of guests simply head straight for the tower and completely ignore the rest of the city. Pisa is a city in Tuscany, Italy, that is home to over 20 historic churches, castles that date back to the middle ages, and ancient bridges that span the Arno River. Although the pretty old town dates back to pre-Roman times, the majority of the structures that are still standing today were constructed between the 9th and 16th centuries. 

You can also go to the Museo dell’ Opera del Duomo, which is located within the cathedral and houses original sculptures created by Nicola and Giovanni Pisano in addition to other priceless works of art that are part of the cathedral’s collection.

The well-known Tower of Pisa, which leans to one side, can be found at the northernmost point of the historic town center. In the Piazza dei Miracoli, the monument, which is actually the bell tower of the cathedral, is just one of many examples of architectural and artistic excellence. The construction of the Cathedral of Pisa began in 1063; however, work on the bell tower did not begin until 1173. After it was finished in 1372, it began to lean almost as soon as it was possible due to the soft and unstable ground.

3. Lucca

The city of Lucca is well-known for the walls that date back to the Renaissance and encircle the Old City. Passeggiata delle Mura Urbane is a pedestrian promenade that was constructed on the city walls after they had served their initial purpose of providing protection against attacks from Pisa and Florence, which were located in the surrounding area.

lucca italy
Beautiful Towns in Tuscany: Lucca

In addition, the Piazza dell’Anfiteatro, which was constructed on the site of an ancient Roman amphitheater, can be found in the old town. There is such a wide variety of things to see and do in Lucca, including the famous opera composer Giacomo Puccini’s childhood home, the Casa di Puccini. In fact, every summer this town plays host to a Puccini opera festival.

When you are in Lucca, make it a point to check out the palaces in addition to the museums. These magnificent buildings were once the residences of Lucca’s aristocracy, and they are truly magnificent. For instance, the Villa Garzoni is well-known for its beautiful water gardens, and the Pallazo Pfanner, which was also renowned for its beautiful gardens, is now used as a museum.

4. Arezzo

Arezzo was a significant city in the time before the Roman conquest, and the Roman historian Livy referred to it as one of the Etruscan capitals. Arezzo is a stunning town that dates back to the Middle Ages, the Renaissance, and Romanesque periods, all of which can be seen in its architecture today.

Arezzo Italy
Beautiful Towns in Tuscany: Arezzo, Italy

The Saracen Joust is a festival that dates back to medieval times and is held every year in the town square. The various neighborhoods of the town are represented by mounted knights who take turns shooting at a target that is attached to a statue of a Saracen king in order to earn points for their level of accuracy. During the festival, virtually everyone in the town dons a costume from the middle ages so they can root for their chosen champions.

If you can’t make it to this festival, don’t worry; Arezzo hosts a number of other food-related events and festivals throughout the year. In addition to this, it is well-known for its assortment of cozy bars, ideal for unwinding during the aperitivo hour.

5. Montepulciano

Montepulciano, a hill town from the Middle Ages and the Renaissance, is perched high on a limestone ridge and is famous for its cheese, pork, thick hand-rolled pasta, honey, lentils, and world-famous wine. Vino Nobile di Montepulciano is regarded by connoisseurs as one of Italy’s top red wines.

Montepulciano Italy
Beautiful Towns in Tuscany: Montepulciano Italy

The majority of the eateries and stores are located along the main street, which runs from Porta Al Prato to the Piazza Grande for less than a mile. In addition, many of the streets in this charming town are car-free, making walking easy. Visit the nearby cathedral while you’re in Montepulciano. It was built between 1594 and 1680. The Assumption of the Virgin by Taddeo di Bartolo, finished in 1401, is a work of art that can be found in this modest cathedral.

6. Siena

sienna italy in tuscany
Beautiful Towns in Tuscany: Siena

UNESCO has also designated Siena’s historic city center as a World Heritage Site. It is renowned for its exquisite cuisine, medieval structures, and museums, making it one of the must-see locations in Tuscany. Another well-known event in Siena is the Palio di Siena, a twice-yearly horse race that features ten bareback riders wearing Renaissance attire. Since the Middle Ages, the historic race has been held in some fashion.

You should go to the Siena Cathedral, a masterpiece of Italian Romanesque-Gothic architecture from the 12th century. The cathedral’s interior features a sizable collection of Renaissance artwork. Old patrician villas, some of which were created by the architect Baldassarre Peruzzi in the 16th century, are also prevalent in Siena. Even though Siena is bursting with art and architecture, just strolling the cobblestoned streets will take you back to those carefree days.

7. Pistoia

Pistoia Italy
Beautiful Towns in Tuscany: Pistoia, Italy

Pistoia is a delicacy that not many people are familiar with. Although it is located in the heart of Tuscany’s tourist district and is only a short distance from Florence, Lucca, and Siena, visitors rarely make the effort to visit it. This shouldn’t come as too much of a shock.

The town is not as grand as Florence; it is not as ancient as Siena; it is not as complete as Luca; and its name probably does not sound as pretty. Yet Pistoia is a gem There are frescoes, striped churches, and old city walls, all of which are essential components of an old Tuscan city. Despite its size, the city center is packed with medieval watchtowers and piazzas with arcades.

8. Livorno

Livorno Italy
Beautiful Towns in Tuscany: Livorno, Italy

Livorno is the capital of the Province of Livorno and one of the most significant cities in Italy, despite not having the highest population. Its enormous port, which is the third largest in the nation, is its main economic engine. A number of cruise ships also dock in its port, giving passengers the chance to tour Italy’s mainland.

Since the Neolithic era, Livorno has shown signs of human habitation, and because of its coastal location in central Italy, it has always been a significant city. Livorno was fortified and received numerous towers, forts, and city walls to aid in its defense during the Renaissance and the Medici family’s rule. The pentagonal shape of the former historic city center and a large portion of these defenses are still visible today.

The city grew over time, and today, with the port’s industrial nature, there is a lovely contrast between the old and the new. Livorno is a fantastic destination in its own right with a ton of historical sites and a stunning coastline that are just waiting to be explored, even though many travelers pass through it on their way to Pisa.

9. Grosseto

Grosseto Italy
Beautiful Towns in Tuscany: Grosseto, Italy

Only a few kilometers from the Tyrrhenian coast, Grosseto, the capital of Maremma, is spread across the plain that the Ombrone passes through. Due to its calm atmosphere and ideal location for exploring the nearby coast and surrounding hills, the city is great for families, but it also has a lot of unexpected surprises in store for tourists.

Medieval walls that have been beautifully preserved and are still intact completely surround the historical center. The Piazza del Duomo, also known as Piazza Dante, is a must-see once in the center. The most significant monument in the city, the San Lorenzo Cathedral, was built in the twelfth century and is known for its remarkable white and pink marble facade.

The cathedral’s interior is designed like a Latin cross, with two side aisles and a nave that ends in a semicircular apse. There are also various intriguing sculptures, such as the impressive marble baptismal font by Antonio Ghini.

Don’t miss the Cassero Senese, one of four ramparts built along the city walls, alongside that of St. Peter, the Sienese rampart and the entrance tower. It was constructed under the rule of the Sienese Republic and finished in 1345. Along the walk through the ramparts, you can find the Church and Convent of San Francesco, which is also worthwhile visiting.

10. Cortona

Cortona Italy
Beautiful Towns in Tuscany: Cortona, Italy

Cortona is a medieval city with steep, winding streets and 2,000-foot-high medieval buildings. You can enjoy a breathtaking view of the entire Valdichiana valley from the town’s high hilltop. These are the settings for the novel Under the Tuscan Sun by Frances Mayes. A superb view of Lake Trasimeno, where Hannibal ambushed the Roman army in 217 BC, is also available from the Piazza Carbonaia.

Parts of the very old Etruscan city wall, which was constructed in the Middle Ages, can still be seen at the base of the current wall. View artifacts from the ancient Etruscan, Roman, and Egyptian civilizations inside the Museo dell’Accademia Etrusca on the Palazzo Casali. The museum additionally showcases works of art and artifacts related to the town’s illustrious Medieval and Renaissance past.

11. Volterra

Volterra Italy
Beautiful Towns in Tuscany: Volterra, Italy

Volterra is a walled mountaintop town that is located not too far from Florence. It has a history that dates back to before the 8th century BC. The town is home to structures and buildings that date back to the Etruscan, Roman, and Medieval eras, which together create a delightfully eclectic mix of architectural styles. One of the best parts of visiting this picturesque town in Tuscany is taking a stroll through the town’s winding, cobblestone streets.

The frescoes in the Church of San Francesco, which was constructed in the 13th century, are one of the attractions in Volterra. The Roman Theatre of Volterra, which dates back to the 1st century BC, is another one of the city’s points of interest. Ancient walls and a formidable fortress can still be seen in Volterra, which has been meticulously preserved. In addition to this, it is well-known as a place to go shopping for artisanal handicrafts made in the local area.

12. Viareggio

Viareggio Italy
Beautiful Towns in Tuscany: Viareggio Italy

Italy’s most well-known seaside destination is the city of Viareggio, which is situated between the Tyrrhenian Sea and the white peaks of the marble mountains. The entire Viareggio center is pedestrian-only, which adds to its peculiarity. It is a charming city with Art Nouveau architecture and a refined and elegant atmosphere that brings to mind Italy in the 1920s.

It is the ideal location for vacations year-round, not just in the summer, with more than 10 km of sandy beaches and close proximity to Lucca and Cinque Terre. The city is renowned for its well-known Carnival as well.

The Margherita Promenade is among this town’s most popular destinations. Following Viareggio’s seafront is the length of the Margherita Walk. This region of the city is also the most historically significant and artistic; in fact, there are some excellent examples of Liberty and Art Deco architecture here that date to the early 20th century.

The path, which is bike- and pedestrian-friendly, winds along the coastline’s beaches and tourist attractions until it reaches a dramatic lighthouse, also known as a panoramic observation point. Small boat docks are a little further away. Due to the abundance of stores, bars, and restaurants, the Promenade can get quite crowded, especially in the evening.

The Clock Tower, Mazzini Square, the Burlamacco Statue, the Burlamacca Canal, the Palace of the Muses with its extensive art collection, and the Politeama Theater are some of the most significant monuments.

Beautiful Towns in Tuscany Guide to Pretty and Scenic Tuscan Adventure pin
Beautiful Towns in Tuscany Guide to Pretty and Scenic Tuscan Adventure


Everything Zany Dual Citizen Travel Blog

Everything Zany

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Everything Zany Travel Blog exploring the UK and beyond. Sharing travel guides, tips, history, and culture. Our travel media brand is founded by travel and hotel industry expert – Ryazan Tristram, a Dual Citizen (British – Filipina) based in Birmingham, UK. Everything Zany is a reputable and award-winning travel blog. Our work and contributions have been featured in Huffington Post, CNBC, Discovery Channel, GMA, Readers Digest, and Lonely Planet. Our missions are to build a great travel community and resource of travel tips, visas, and travel guides for travelers. Join us as we travel around the UK and beyond with a mission to share the best of the world.

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