Who doesn’t love a bit of Tuscany? Sun-drenched medieval villages perched atop rolling hills, acres of vineyards, delicious food and wine – it’s no wonder this region is one of Italy’s most popular tourist destinations. Tuscany is located in central Italy with a reputation for its stunning landscapes, mouthwatering cuisine, and rich cultural heritage. But with so many gorgeous towns and villages to choose from, where should you go in Tuscany? Here are our top 20 picks to add to your itinerary. PS: Don’t forget to pack your walking shoes!

1- Florence

Florence is one of the most popular travel destinations in Tuscany. And it’s no wonder why – the city is absolutely gorgeous, with plenty of historical and cultural sites to keep visitors entertained. 

Florence is also home to some of the best food in the country, so be sure to sample as much as you can while you’re there! 

Whether you’re looking to explore world-famous museums or simply soak up the atmosphere of this beautiful city, Florence is sure to enchant you.

2- Siena

Siena is a city in Tuscany. It is known for its art, cuisine, history, and culture. The city is situated on a hillside, and its name comes from the Latin word for clay, siena. 

Siena was founded by the Etruscans in the 8th century BCE, and its golden age was during the 12th and 13th centuries. 

The main attractions in Siena are its cathedral, which is built of white marble, and its town square, which is known as the Piazza del Campo. 

Both of these sites were constructed during the Middle Ages. Siena is also home to a number of museums and art galleries. 

The most famous painting from Siena is The Birth of Venus by Botticelli.

3- Arezzo

The city of Arezzo is located in the heart of Tuscany and is known for its beautiful medieval churches and historic buildings. 

Visitors to Arezzo can explore the city’s well-preserved walls and towers, or visit the lively open-air market held every first Sunday of the month. 

Arezzo is also home to a number of prestigious museums, including the Museo Statale d’Arte Medievale e Moderna, which houses an impressive collection of Italian art. 

With its picturesque setting and wealth of things to see and do, Arezzo is an ideal destination for a day trip or a longer stay.

4- San Gimignano

San Gimignano is a small town located in the Tuscan region of Italy. It is most famous for its medieval towers, which rise up from the hilltop town like sentinels. 

San Gimignano was once an important stop on the Via Francigena, a pilgrimage route that ran from England to Rome. 

Today, the town is a popular tourist destination, and its narrow streets are lined with shops and restaurants.

 

Visitors can also explore the town’s many churches and museums, or take a short drive to the nearby vineyards. 

With its picturesque setting and fascinating history, San Gimignano is definitely worth a visit.

5- Pisa

Pisa is a city in the Tuscany region, best known for its Leaning Tower. Although the marble structure famously leans to one side, it’s actually the entire cathedral complex, located on the “Field of Miracles,” that’s tilting. 

The complex includes the Baptistery, crypts, cemetery and an outdoor pulpit. The Duomo, or cathedral, has intricate striped arches and rows of botanical-themed mosaics on its ceiling. 

Pisa is also home to the University of Pisa, founded in the 11th century.

6- Lucca

Lucca is a beautiful city in Tuscany that is known for its Renaissance-era walls. The city is home to many historical and architectural landmarks, as well as a number of museums and art galleries. 

Visitors to Lucca can enjoy strolling through the winding streets, admiring the ornate churches, and sampling the local cuisine. 

With its charming atmosphere and rich history, Lucca is an ideal destination for anyone looking to experience the best of Italy.

7- Pistoia 

Pistoia is a Tuscan city located in the Tuscan region about midway between Florence and Lucca, and it’s a great place to visit if you’re looking to escape the hustle and bustle of those larger cities. 

Pistoia is home to a number of historical churches and palaces, as well as a picturesque central square where you can enjoy a coffee or gelato. 

The city also has a lively market where you can find everything from fresh produce to handmade goods. If you’re interested in Italian history, Pistoia is definitely worth a visit.

8- Montepulciano

Montepulciano is a medieval and Renaissance hill town and comune in the Tuscan province of Siena. The town is located about 20 miles south-east of Siena, on a spur of land between the valleys of the Arno and the Chiana. 

The name Montepulciano is derived from the Latin words “mons”, pulcher, and “ianus”. The slopes of Montepulciano are home to the famed Vino Nobile di Montepulciano, a red wine produced from the Sangiovese grape. 

The wine was first produced in the 14th century and gained in popularity over the centuries. 

Today, it is one of Italy’s most famous wines, and visitors to Montepulciano can tour the many wineries that produce it. 

In addition to its wine production, Montepulciano is also known for its art and architecture. 

The town’s historic center is full of medieval and Renaissance buildings, including several churches and palaces. 

Visitors can also enjoy views of the Tuscan countryside from Montepulciano’s high vantage point. 

With its stunning setting, rich history, and delicious wine, Montepulciano is a must-visit destination in Tuscany

9- Montalcino

Montalcino is another Tuscan hilltop town situated on top of a hill and offering stunning views of the surrounding countryside. 

Montalcino is most famous for its wines, which are some of the best in all of Italy. 

The town is also home to a number of historic churches and buildings, making it a popular destination for tourists. 

While Montalcino may be best known for its wines, the town has much more to offer visitors. 

With its stunning views, historic churches, and excellent restaurants, Montalcino is a must-visit destination for anyone traveling to Italy.

10- Val d’Orcia

Val d’Orcia is a Tuscan valley that extends from the hills near Siena to the border with Umbria. 

The valley is dotted with towns and villages, including San Quirico d’Orcia, Pienza, and Montepulciano. 

The landscape of the valley is characterized by gentle rolling hills, vineyards, and olive groves. 

The area was designated a UNESCO World Heritage Site in 2004. 

Val d’Orcia is a popular tourist destination for its scenic beauty and its attractions, which include the Cathedral of San Biagio in Montepulciano and the thermal baths of Bagno Vignoni.

11- Pienza

Pienza is a town in the province of Siena, in the Italian region of Tuscany. It is notable for its production of pecorino cheese, as well as for its Renaissance architecture. 

The town was founded in the 15th century by Pope Pius II, who commissioned the architect Bernardo Rossellino to design a new urban center. 

The result was a harmonious blend of Renaissance and Medieval elements, which has led Pienza to be designated as a UNESCO World Heritage Site. 

Today, the town remains popular with tourists, who come to admire its architecture and enjoy its Tuscan cuisine.

12- Monteriggioni 

Monteriggioni is a small walled town located in Tuscany. 

It sits atop a hill overlooking the Tuscan countryside, and is surrounded by olive groves and vineyards.

 

Visitors to Monteriggioni can explore its medieval streets, visit its museums and churches, or simply enjoy the view from its walls. 

The town is best known for its annual festival, which celebrates the Battle of Monteriggioni – a key victory won by the Republic of Florence during the Italian Wars. 

Today, Monteriggioni is a popular tourist destination, and its festival draws visitors from all over Italy. 

If you’re looking for a taste of Old World charm, Monteriggioni is definitely worth a visit.

13- Chianti

The Chianti region is located in central Italy and is known for its namesake wine, as well as its picturesque landscape of rolling hills and olive groves. 

The region has a long history of viticulture, dating back to the Middle Ages, when the first vineyards were planted by the noble families who ruled over the area. 

Today, the Chianti region produces some of Italy’s finest wines, made from a mix of indigenous and international grape varieties. 

The climate is relatively warm and dry, which helps the grapes to ripen fully and develop complex flavors.

 

The Chianti region is also home to a number of medieval towns and villages, which add to its charm and appeal. 

Visitors to the area can tour wineries, stroll through quaint streets, and enjoy views of the Tuscan countryside.

14- Pitigliano

Pitigliano is a small town in southern Tuscany. The town is built on a tufa outcrop and is surrounded by deep ravines. 

Its name comes from the Latin word for “little pinnacle.” Pitigliano is known for its wine and olive oil production. The town’s coat of arms depicts a grape vine and an olive branch. 

Pitigliano has a long history dating back to the Etruscan era. The town was settled by the Roman Empire and later became part of the Republic of Siena. 

In 1553, Pitigliano was conquered byCosimo I de’ Medici, the first Grand Duke of Tuscany. Today, Pitigliano is a popular tourist destination. 

Visitors come to see the town’s well-preserved medieval architecture and to enjoy the local wine and cuisine.

15- Island of Elba

Elba is a beautiful island off the coast of Italy. It’s well known for its clear blue waters, sandy beaches, and picturesque villages. 

One of the best things about Elba is that it’s relatively unspoiled by tourism. That means you can still find quiet, secluded spots to relax and enjoy the island’s natural beauty. 

Whether you’re looking for a relaxing beach vacation or an adventure-filled getaway, Elba is definitely worth a visit.

16- Volterra

Volterra is a small town located in the province of Tuscany, about midway between Florence and Pisa. The city is known for its art and architecture, as well as its rich history. 

Volterra was founded by the Etruscans in the 8th century BC, and it soon became an important center of trade and culture. 

The Roman Empire took control of the city in the 2nd century BC, and it remained an important Roman town for centuries. 

These days, Volterra is a popular tourist destination, with visitors coming to see its ancient ruins, beautiful churches, and stunning views. 

If you’re ever in central Italy/ Tuscany, be sure to add Volterra to your list of places to visit!

17- Cortona

Cortona is a beautiful Tuscan town that sits atop a hill in the south of Tuscany. 

The town is known for its medieval architecture and stunning views, as well as its lively culture and excellent food. 

Visitors to Cortona can explore the well-preserved historic center that dates back to the 14th century, wander through the cobbled streets, and enjoy the town’s many cafes, bars, and restaurants. 

There are also a number of museums and art galleries to be found in Cortona, making it the perfect destination for those interested in culture and history. The MAEC MUSEUM is a great place for those who want to know more about the Etruscan civilisation.

Whatever your interests, Cortona is sure to offer something for everyone.

18- Grosseto 

Grosseto is a city in central Italy, about 130 kilometers southwest of Florence. 

It’s the capital of the province of Grosseto and the main town in the Maremma region. The city’s origins date back to the 10th century, when it was founded by the Lombards. 

In the 13th century, it became a free commune, and in 1254 it was conquered by Siena. Grosseto prospered as a trade center and medieval fair ground. 

However, in the 16th century it was sacked by Barbary pirates, and later it suffered from plague outbreaks. 

Grosseto’s historic center is surrounded by medieval walls with towers and gates. 

The centerpiece of the town is Piazza Dante Alighieri, which features a fountain and a statue of the Italian poet Dante Alighieri. 

Other notable landmarks include the Duomo (cathedral), Palazzo Ducale (ducal palace), and Pinacoteca e Museo Civico (art museum). 

Grosseto has a population of about 86,000 people.

19- San Quirico d’Orcia

San Quirico d’Orcia is a small town in the heart of Val d’Orcia. The town is most notable for its well-preserved medieval architecture and scenic location in the Orcia Valley. 

The streets of San Quirico are lined with handsome stone buildings, many of which date back to the 13th century. 

The town’s central square, Palazzo Chigi, is home to a beautiful townhall. 

From the town, there are sweeping views of the valley and its vineyards and olive groves. Just outside of town is the thermal springs of Bagno Vignoni, which have been popular since Roman times. 

Visitors can still soak in the springs’ waters, which are said to have therapeutic properties. 

With its beautiful setting and rich history, San Quirico makes for an enjoyable day trip from nearby cities such as Florence and Siena.

20- Vinci

Vinci is a small town located in Tuscany. The town is most famous for being the birthplace of Leonardo da Vinci, one of the most celebrated painters and inventors of all time. 

Visitors to Vinci can see several buildings that date back to Leonardo’s time, including the church where he was baptized. 

The town also has a museum dedicated to Leonardo’s life and work, which features some of his original sketches and notebooks. 

In addition, Vinci is surrounded by beautiful countryside that is perfect for hiking or enjoying a leisurely picnic. With its fascinating history and scenic setting, Vinci is definitely worth a visit.