The prettiest towns in Tuscany you must see

While it is hard to choose the prettiest towns in Tuscany, the region is undoubtedly home to some of the most picturesque places in Europe.

Tuscany is known for its rolling hills, beautiful valleys, and some of the best wines in the world. It is also brimful of history, art, and culture. After all, it was the center of the Italian Renaissance.

Given this background, every little village is a kind of a masterpiece in its own way.

Even so, a select list of towns stand out with their architectural beauty and natural surroundings. This article is about some of these.

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Table of Contents
  1. The prettiest towns in Tuscany
    1. Where to fly into for visiting Tuscany?
    2. How to travel around Tuscany
    3. How many days to spend exploring Tuscany?
    4. Prettiest Towns in Tuscany
      1. Siena
      2. Monteriggioni
      3. Lucca
      4. San Gimignano
      5. Panzano
      6. Volterra
      7. Pienza
      8. Montecatini Terme
      9. Montepulciano
      10. Pitigliano
      11. Pisa
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The prettiest towns in Tuscany

Where to fly into for visiting Tuscany?

While there are many options for getting to Tuscany, these two most important regional airports will set you close to the Tuscan villages you’ll visit: Florence and Pisa

The Pisa Airport, Galileo Galilei, is larger than the one in Florence and is serviced by low-cost and line companies such as British Airways, Lufthansa, Turkish Airlines, or Qatar. 

Check out the best flights from your location here: Kiwi.com!

How to travel around Tuscany

While Northern Italy has excellent infrastructure and public transportation, renting a car is the easiest way to visit all the beautiful towns in Tuscany. 

Imagine driving around in a tiny Fiat 500, passing by olive tree orchards and historical villas!

Discover Cars is my go-to tool for renting cars. It is a great aggregator that can help you save up to 70% on your car rental.

Get your offers here!

How many days to spend exploring Tuscany?

That depends on many factors, starting with your travel style and ending with the budget you have allocated for this trip.

You can easily spend a long weekend wandering around the winding roads of Tuscany, but you can also come here for a few months without ever getting bored! We spent a month there and couldn’t get enough of the place.

Prettiest Towns in Tuscany

Siena

prettiest towns in Tuscany

By Inguaribileviaggiatore.it

Siena is one of the primary and most visited cities in Tuscany. It is known for its enormous historical, artistic, and landscape heritage and the famous Palio.

A full day in Siena is certainly not enough to experience the city’s nuances and see all its heritage, so it is better to spend two days there.

The dominant color in Siena is red, which is the color of the Tuscan terracotta of the houses and roofs, which makes the prestigious marble buildings stand out even more. Above all, the black and white of the Cathedral stands out imperiously and is visible from most of the city. Also, the Gothic-style Palazzo Salimbeni is made of stone in the beautiful Piazza Salimbeni.

However, the city’s beating heart is Piazza del Campo, where the three hills join.

Among the things to see in Siena is the beautiful Gaia fountain. The work takes this name because of a great party organized by the Sienese. The Gaia fountain was the first to allow drinking water up to Piazza del Campo, which was probably not very simple then.

The Piccolomini library was built in 1492 to house the books of Pope Pius II and was decorated in the early 1500s by Pinturicchio and aides, including Raphael. The frescoes tell of the life of Enea Silvio Piccolomini, who became Pope with the name of Pius II.

When you enter this library, you don’t know where to look—whether it’s a jewel in the books, the ceiling, or the frescoes!

The best tours in Siena:

Monteriggioni

Monteriggioni_villages in Tuscany

By Travel with the crew

When you travel through Florence, you must stop to see Monteriggioni. This charming Tuscan town is home to many historical monuments. Monteriggioni is located on a hilltop and had its “golden age” between the 14th and 15th centuries.

It started life as a fortified castle and became a town in 1630. It was also the stronghold of many noble families, leaving a vital heritage of art and architecture.

Although the town of Monteriggioni is relatively small, it is iconic due to its unique fortress walls. The city is surrounded by a high, 5m thick wall built in the Middle Ages.

The main attraction in Monteriggioni is its castle. Built between the 13th and 15th centuries, it today hosts many cultural events, such as concerts and festivals. The castle has 14 unique towers that give an unimpeded view of the town and surrounding countryside.

In Monteriggioni, there are other places worth visiting besides the castle, such as Santa Maria and Piazza de Roma.

If you visit during July, you can see the Medieval Festival at Monteriggioni each year. Recreations of life during the Middle Ages, craftsmen, soldiers, and more give you a peek at life long ago.

The best way to get to Monteriggioni is by car as it is direct and parking is easy. You can also take the bus from Florence, but the ride is a little longer as it stops along the way.

The closest airports are Pisa and Florence Airports

Best tours that will take you to Monteriggioni:

Lucca

prettiest towns in Tuscany

By Brainy Backpackers

Lucca is one of the underrated yet impressive destinations in Tuscany. Whether you’re on a day trip from Pisa or Florence or on a Tuscany road trip, you’ll want to visit more of this fantastic region in Italy.

Among the main attractions are the Torre Delle Ore towers and the Guinigi Tower, which offer views of the old town. You should also visit the cathedral, which is decorated with unique columns. Lucca might be best known for San Michele in Foro and the Basilica of San Fernando.

Make sure you head to Piazza dell’Anfiteatro to eat pizza or at least for a drink. The unique square is built on top of the old amphitheater, and the buildings outline the walls that are buried underground, forming an oval circle of pastel-colored houses.

While you can see most of Lucca’s attractions in a day, it is worth spending a few days in this charming town to get a good feel for it. There are public parking lots outside the town walls, but it is not allowed to drive inside the old city for unauthorized vehicles.

If you don’t drive, you can get to Lucca by bus or train from Florence in less than 2 hours and from Pisa in only 15-20 minutes.

Best tours in and from Lucca:

San Gimignano

San Gimignano, Italy

By PlacesofJuma

One of the most beautiful towns in Tuscany is undoubtedly San Gimignano. This charming place is located in hilly Tuscany, 50 kilometers south of Florence, and is for many a must-see on any round trip. The best way to get there is by car or booking an excursion. It is also worth spending 2-3 days exploring the surrounding destinations (e.g., Chianti, Siena, and Monteriggioni).

San Gimignano is often called “Medieval Manhattan,” the old town is listed as a UNESCO World Heritage Site. In particular, the many tall medieval towers form an imposing backdrop. Some towers are up to 50 meters high, and 14 of the former 72 are still well preserved today. Because of its good state of preservation, the entire town center of San Gimignano has been included in the UNESCO World Heritage List.

A walk through the old stone streets of the historic old town is genuinely romantic. At almost every corner, you will discover a monument or a sight and countless opportunities for beautiful photos. Don’t forget to try the ice cream at Gelateria Dondoli in the main square, Piazza Della Cisterna. It has been voted ice cream world champion twice!

Suppose you want to spend a holiday here. In that case, we recommend the Castello di Fulignano – a beautiful castle with flats, a vast pool, and a magnificent panoramic view over the Tuscan hills.

Best tours in San Gimignano:

Panzano

Panzano hills Tuscany

By May Cause Wanderlust

Deep in the rolling hills of the Chianti region of Tuscany is a small town called Panzano. Its cluster of red-roofed houses is surrounded by picturesque vineyards punctuated with poplar trees. Like many other towns in Tuscany, Panzano is charming, peaceful, and idyllic. However, what sets Panzano apart is a complex of restaurants from a legendary chef, Dario Cecchini, known affectionately as the Butcher of Panzano.

If you watch Chef’s Table on Netflix, you may have heard Dario’s story. He grew up loving animals and wanted to be a veterinarian, but was obligated to take on the family’s butchery business when his father died. He felt very conflicted between his desire to help animals and his desire to look after his family. After some time, he found a way to resolve this conflict: to respect the animal’s gift and to use every part of its body when it dies. His restaurants, which include Solociccia, right next to his butcher’s shop, practice nose-to-tail eating. His set menus include all parts of a cow, transformed into creative dishes and served in one sitting on communal tables, often to great fanfare and clapping, in honor of the food. The celebratory atmosphere is terrific!

It is worth spending at least a day in Panzano, about an hour by car from Florence. If you don’t eat meat, skip Dario’s restaurants, but don’t skip the Il Palagio di Panzano wine shop opposite – they offer local wine tastings and glorious views over the rolling Tuscan hills.

Volterra

prettiest towns in Tuscany

By Tourist to travellers

The old historic town of Volterra in Tuscany is known for its numerous attractions and countless archaeological sites. This beautiful town is also a historic center and is popularly known as the “City of Alabaster” because of the alabaster processing here.

Volterra is known for its rich Etruscan heritage, dating back to the 4th century B.C. Tourists can soak up the town’s history.

Piazza Dei Priori is one of the must-see places in Volterra. It’s the main square of the medieval town. Enjoy a cup of coffee in one of the cafes and enjoy the view.

The Etruscan Museum is one of the oldest museums in Europe. Its collection includes beautiful ceramics and urns.

Palazzo Incontri Viti hosts a museum that provides insight into the lives of the Volterra royals and contains the relics of the Viti family.

One of the most important archeological sites of Volterra is the Roman Theatre.

Go on a tour:

Pienza

Pienza Tuscany

By Italy Foodie

There are so many beautiful towns in Tuscany, and Pienza is one of the best.

Located on a hill overlooking the stunning Val d’Orcia, Pienza is 117km (73 miles) south of Florence. It’s an easy and scenic one-and-a-half-hour drive, or if you’re staying in nearby Montepulciano, it’s just 20 minutes away and well worth the beautiful drive.

In 1996, Pienza was named a UNESCO World Heritage Site. As the birthplace of Pope Pius II, it was considered “the ideal city of the Renaissance.” The Pope had the town completely remodeled to reflect the height of the Italian Renaissance.

Visitors should visit Piazza Pio II, the central town square, to see this unique architecture. Here you will find the Papal Palace, town hall, the ‘well of the dogs’, and the Cathedral of the Assumption, completed in 1426, along with its octagonal bell tower.

One of the most compelling reasons to visit Pienza is the traditional Tuscan food and excellent wines. The village is at the heart of an area that has drawn foodies and wine lovers into the know for years. A must-try is Pecorino di Pienza, a hard cheese made from sheep’s milk that this region of Tuscany is famous for.

If you have the time, plan and take advantage of a food and wine tour. Pienza is a great day trip to try wines and have an incredible dinner.

Tours that will take you to Pienza and useful entry tickets:

Montecatini Terme

prettiest towns in Tuscany

By Dymabroad

One of the best towns to see in Tuscany is Montecatini Terme. It is a small town between Florence and Pisa. It is a lovely town with some exciting things to do and see.

Besides that, its central location makes it perfect as a base for exploring more of Tuscany.

One of the best things to see in Montecatini Terme and the sight for which it is known is the Parco Delle Terme. This spa complex has beautiful architecture. Another of the best things to do in Montecatini Terme is riding the funicular to the top of a hill, where you can find Montecatini Alto.

From there, you have a fantastic view of the town. Another top sight in the town is the MO. C. A, Montecatini Contemporary Art museum. This is an interesting museum with modern art housed in a historical building.

Getting to Montecatini Terme is easy. A train station connects the town to other places in Italy. The town can also be reached by car from different cities in a short amount of time. From Florence, it takes about 45 minutes to reach the city by car.

Get your entry ticket to the Thermal Pool!

Montepulciano

Montepulciano Tuscany

By Merryl’s travel and tricks

Montepulciano is an ancient town in Tuscany known for its fine red wine and beautiful countryside views. It can be reached easily by road from Florence or Rome in about 1.5-2 hours. It is the perfect town for anyone who loves authentic food and excellent local wine and wants to experience the Tuscan countryside.

The ancient city center of Montepulciano is filled with pretty squares, renaissance palaces, ancient churches, charming corners, and unmatched views of Val d’Orcia and Val di Chiana. Piazza Grande is the main square in the town and has plenty of bars dotted around it for a quick coffee stop. The city is also known for the typical red Montepulciano wine. You will find little cantinas dotted through the city offering free product tastings.

For food lovers, this town has plenty to offer. Everything is fresh and locally produced, from pasta to steak, cold cuts, and cheese. Osteria Acquacheta is the place for local pasta and the famous Fiorentina steak. Try the Pici alla Cinghiale, a pasta with wild boar meat sauce, or the Pici all’Aglione for vegetarians. You can also try a variety of local cheeses and salamis at the cantinas in the town.

Here are the most popular tours you should take in Montepulciano: 

Pitigliano

Pitigliano

By Travel Connect Experience 

Pitigliano is a small town in southern Tuscany, a few kilometers from the border with Lazio. One of Italy’s most picturesque medieval towns, it is part of a geological, historical, and archaeological area called “Tuscia.” The towns of Tuscia stand on spurs of tufa rock surrounded by streams and thick, lush vegetation. In fact, from the small terraces at the edge of Pitigliano, you can enjoy a breathtaking view of the gorges surrounding it.

However, the landscape is not the only strong point of Pitigliano, which is rich in historical monuments.

In the first half of the 17th century, the noble Medici family of Florence built a monumental aqueduct with 15 arches to supply the town with water. The aqueduct culminates with the ” Fountain of the 7 Spouts,” decorated with bas-reliefs of different historical periods.

Along the main street, “Via Roma,” there are souvenir stores and workshops for artists. Going all the way, you get to a small piazza dominated by the facade of the Cathedral of Saints Peter and Paul, dating back to the 13th century but then renovated. On one side of the square, from an arcade, you can access a stone staircase connected to the alley below, where there is the Jewish Quarter, one of the oldest in Europe, with the Synagogue and a museum.

It takes about 3 hours to explore Pitigliano’s alleys, squares, and hidden viewpoints.

The town is also immersed in the archaeological area “Cities of Tuff,” which includes miles of nature trails through the fascinating streets carved into the rock by the ancient Etruscans in pre-Roman times.

Pisa

prettiest towns in Tuscany

By The Purposely Lost

Although most visitors only spend one day in Pisa, it’s one of the best towns in Tuscany. The city’s most iconic landmark is the Leaning Tower of Pisa. The magnificent tower was constructed in the 12th century, but it was already leaning by the time the second story was started.

Although some mistake it for a lookout, the Tower operated as the bell tower for the adjacent Cattedrale di Pisa. In addition to the Tower and Cathedral, there is a baptistry and a cemetery.

Because most tourists only visit Pisa to see the Tower, the remainder of the city is quiet. Walking along the Arno River, which runs directly through the town, and its side streets will give you a good sense of the local culture. Fantastic coffee shops and small merchants surround the numerous distinct town squares.

Pisa also boasts a lovely shoreline, Marina di Pisa, despite the major city center being inland from the coast. Pisa is a fantastic city in Tuscany, with everything from huge, famous sites to smaller, local neighborhoods and a gorgeous beach.

Tours and tickets you must have when visiting Pisa:

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