Best 35 Places To Visit In Tuscany, Italy - Updated 2024

best places to visit in tuscany
Vanna
Vanna 
Contributing Writer
Updated
| 19 min read

Ever watched Under the Tuscan Sun? How about A Room with a View? What about Hannibal starring Anthony Hopkins? Life is Beautiful? Much Ado About Nothing? Wait, hold on– what’s with all the movies? All these films were shot and set in Tuscany, that wondrous region in Central Italy. Ever so sprawling, this expansive pocket stretches from the mountains to the city, with the plains and the hilly countryside in between. No wonder a lot of movies and stories are set here– it’s simply magic. An arresting place to be. As for the accommodations, you can choose from best farm stay to luxury hotels.

Tuscany’s capital is Florence (or Firenze, if you want to be more romantic), but the region has so much more to offer. Here, we count down the best places to visit in Tuscany, Italy.

Popular picks in Tuscany

  • Nature lovers visiting Florence can head to Bardini Garden, which also features a blend of three styles. The Italian garden with a Baroque staircase, the Anglo-Chinese forest with tropical vegetation, and an agricultural park with a new orchard of plums, peaches, and other trees.

  • History buffs can choose from various museums in Tuscany, such as Santa Maria della Scala in Siena where you can learn about the Italian culture. Other popular museums include the Uffizi Galleries in Florence and the Paper Museum in Pescia.

Tip from tour guide

Joanna

Joanna
Tuscany

Tuscany is suitable for different kinds of tourists in different seasons. Read this to find out the best time to visit for you.

- Winter (December-February): These are perfect months for art and museum lovers and people looking for a budget-friendly holiday. Museums are less crowded and hotels, transportation, and tickets cost less. However, the weather can be rainy and many restaurants are closed, especially after the Christmas festivities.

- Spring (March-May): These are the ideal months to dive into the greenest side of Tuscany. The nature explodes, and the hills of Chianti and Val d'Orcia come to life. Slowly, the number of tourists increases, but it's still not too much. However, Florence is usually crowded in April and May.

- Summer (June-August): You can avoid visiting in these months if you're interested in checking out the museums. The temperature can reach even 40 °C. This is the best time for sea lovers and mountain explorers or those who just like to chill with a glass of wine in the countryside hotels. In July and August, seaside locations are usually full, so you have to book in advance.

- Fall (September-November): This is the perfect time to visit Tuscany. The temperature goes down, but until the end of October, you can still enjoy swimming in the sea. The hotel prices significantly drop during these months. November usually marks the first days of rain and wind.

1. Pisa

Best known for its leaning tower, which has come to be one of Italy’s most enduring symbols and landmarks, Pisa is a destination not to be missed while you’re in Tuscany. It is located by the coast, with the Ligurian Sea to its west and the Arno river bisecting the city into two halves. Nobody knows who established Pisa (some say it’s the Pelasgi, some say it’s the Greeks), when it was founded, and where its name even came from, but one thing’s for sure: one day here will be packed with activities.

In just 24 hours, you can squeeze a number of attractions, starting with the Tower of Pisa to the Clock Palace and then the Piazza dei Cavalieri. I would love to take it slow and take a casual stroll along the river with my partner, then just stop by any shop, restaurant, or interesting site.

Good to know:

  • One of the most historic and picturesque neighborhoods in Pisa is Santa Maria, located near the iconic Leaning Tower of Pisa. The famous Piazza dei Miracoli, which houses the Leaning Tower, the Cathedral of Santa Maria Assunta, and other attractions is also located here.

  • For more information, check out the tourism board page.


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2. Carrara

Carrara is undoubtedly one of Tuscany’s more underrated gems, but for many of Italy’s artists, it’s a great source of inspiration and material. It’s because Carrara is one of the best places to get marble, with quarries in and around the city, scattered all over the province. Carrara has been supplying marble for 2,000 years that even some of the antiquities’ greatest landmarks, such as the Pantheon, feature Carrara marble.

As a commune, Carrara is quiet and slow-paced. Must-visit sites include the Cathedral, which dates back to the 12th century, and the Ducal Palace, which now houses the Fine Arts Academy. Explore the town and the quarries, or take the short drive to the coast and spend a day at the beach.

Good to know:

  • Carrara is known for the prestigious Academy of Fine Arts, which specializes in the arts related to marble carving and sculpture. Founded in 1769, the academy has trained many famous sculptors and continues to attract students from around the world.


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Tip from tour guide

Joanna

Joanna
Tuscany

David by Eduardo Kobra

When in Carrara, stop by the mural of David by Eduardo Kobra. In 2017, one of the most popular street art artists in the world, Kobra, delivered a 12-m-high (39 ft) and 20-m-wide (65 ft) mural in Carrara. He painted David at the top of one of the quarries, directly on the marble.

Kobra was born in 1976 in Brazil. He started as a graffiti artist in his hometown, São Paolo. Self-taught, he took inspiration from Banksy, Diego Rivera, Keith Haring, and Eric Grohe. He has worked on many murals in Brasil, the United States, Mexico, and Europe.

To reach the mural, you can follow the hiking trail from Colonnata or Bedizzano in the Apuane mountains.

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3. Piombino

Piombino, veduta dalla cittadella 02
Source: Photo by Wikimedia Commons user Sailko used under CC BY 3.0

If you are road tripping down the Etruscan Coast, the small town of Piombino would be your final stop. Just as well, for this sleepy coastal commune has plenty to offer. I feel this place is perfect for history buffs who’re interested in learning about its past secrets. There’s the town’s defensive wall, which actually bears traces of Leonardo da Vinci’s work. Monuments abound, including the Casa delle Bifore, which dates back to the 14th century. Piombino also has a collection of wondrous churches, chief of which is the Church of the Immacolata. Since Piombino dates so far back in history, archaeologists have found a bevy of artifacts in the town. You can view a large portion of these cultural treasures at The Populonia Archaeological Museum.

Piombino is also a jump-off point for other adventures off the Tuscan coast. From here, you can board a ferry to explore the Tuscan archipelago and the Gulf of Baratti.

Good to know:

  • Piombino’ Co-Cathedral of Sant’Antimo is a beautiful church dating back to the 14th century. Dedicated to St. Augustine, the cathedral boasts Sienese Gothic style of architecture.

  • You can visit the tourism board website for more details.


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4. Florence

When in Tuscany, it’s hard to resist the charms of Florence, the region’s capital city. Florence offers a visual, culinary, and cultural feast with its museums, architecturally significant buildings, trattorias and osterias, and a whole lot more. Spending just a day here is virtually impossible.

One of the largest cities in Italy, Florence is the place to go to experience the best of Italian Renaissance art and culture, which in my opinion is the ideal destination for art connoisseurs. This is where the great masters, such as Boticelli, Michelangelo, Giotto, and Bronzino played and created magnificent works of art. Literary masterpieces were birthed here as well, written by the likes of Niccolo Macchiavelli, Dante Alighieri, and Petrarch. Strolling the streets of Florence alone will give you enough inspiration to last you a lifetime.

Good to know:

  • The historic center of Florence was designated a UNESCO World Heritage Site in 1982 due to a plethora of artistic treasures and architectural masterpieces, including the Florence Cathedral of Santa Maria del Fiore, the Basilica of Santa Croce, and more.

  • Check out the tourism board page for more details on this city.


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Traveler's tips

Good Tip

📍 Florence, Italy [August 2023]

Spent five beautiful days exploring Florence and nearby Tuscan hill towns. On our last day, my husband and I headed up to Piazzale Michaelangelo, where people can enjoy panoramic views of Florence and the Arno River (one of Italy's most important waterways). As you can see, it was crowded, but it was a great way to end this chapter of our month-long Europe trip. ❤

The bridge near the foreground is the famed Ponte Vecchio, which is lined with designer jewelry shops. It's another iconic sunset spot in Florence. The domed church in the distance is Florence's Duomo, which was once known as the Cathedral of Santa Maria del Fiore. Brunelleschi's dome is a stunner whether you're looking at it from afar or up close.

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Florence and Tuscan Hills Vespa Tour with Italian Cuisine Meal

Duration: 6 hours

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Tuscany Tour Guide

Joanna

Joanna

Hello, my name is Joanna. I was born and raised in Poland but then I fell hopelessly in love with Tuscany and have been living in Florence for 20 years. Wisely enough, I decided to turn my passion into work and became a tour guide. Now I can share with you my immense love for the beauty, history and art of these enchanted places. I am particularly passionate about the Middle Ages, history, scu... Read more

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Sara Pallabazzer

Sara Pallabazzer

I am a lively well-spoken tour guide and tour leader from Florence, and a person who has the ability to motivate different sets of audience; to communicate effectively and possesses a high degree of energy and enthusiasm.I am able to manage multiple tasks, self-motivated team player with excellent communication skills. I am proficient in Italian, English and Norwegian and possess a strong love ... Read more

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5. Cortona

Perched on a hilltop overlooking the Tuscan countryside, Cortona in Southern Tuscany fits the image we have of the region perfectly. Tuscan-style villas, dark green cypress trees lining the roads, and panoramic views of the rolling countryside offer postcard-worthy pictures. Cortona was highly prized back in the medieval age for its strategic location, and today, it’s an important center for the arts in the Arezzo Province.

Cortona’s narrow streets are lined with several points of interest. There’s the Diocesan Museum, which houses a panel painting of the Annunciation. The Girifalco Fortress, being the highest place in town, offers the best views of this part of Southern Tuscany. Cortona also offers great shopping and dining– it’s not hard to find specialty shops selling local and handmade crafts, and dark cellars where you can find bottles of full-bodied red wine to add to your collection. As an explorer, I love to buy the specialty items of the area I am visiting. I will surely buy the local handicrafts to add to my collection whenever I visit here.

Good to know:

  • Cortona is one of the oldest towns in Italy, with roots dating back to the Etruscan period. You can view the town’s Etruscan heritage at Accademia Etrusca.

  • Visit the toursim board page to learn more.

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6. Montalcino

Montalcino, Tuscany, Italy
Source: Photo by Wikimedia Commons user Type17 used under CC BY-SA 2.5

Located in the province of Siena, Montalcino is another town you should add to your list of places to visit in Tuscany. It might be another one of those classic hilltop towns that look like they came straight out of fairy tales, but Montalcino is especially notable for one thing– Brunello red wine. Oenophiles from all over the world regularly make the pilgrimage to Montalcino to get bottles of this locally produced wine, made in the vineyards surrounding the town.

Brunello wine (considered as one of Italy’s best and most expensive) isn’t the only reason why you should visit Montalcino. The 12th-century fortress in the heart of town is a must-see, as is the Palazzo dei Priori, where you can find another town landmark: the clock tower.

Good to know:

  • The town is known for its majestic Fortress of Montalcino, which was built in the 14th century and offers breathtaking views of the surrounding countryside.


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7. Pistoia

Tuscany’s garden, Pistoia is renowned in different parts of the world for its tradition of cultivating plant nurseries, which is something the locals have done since the town’s early days. If Montalcino is for fine, Pistoia is for fresh flowers, which you can get in bouquets in the numerous flower markets that spring up around town. Thermal baths are another thing here, with the ones in Monsummano and Montecatini considered as the most popular. I am excited to try new things while traveling and will surely visit one of the thermal baths here. During winter, Pistoia becomes a sports haven, especially among ski enthusiasts who climb up the Pistoia Mountains to run down its slopes. So, flowers, plants, thermal baths, and skiing. What else can you find in Pistoia? Artisan chocolate, of course!

Good to know:

  • Pistoia has a rich tradition of medieval jousting, known as the “Giostra dell’Orso” (Joust of the Bear), held in Piazza del Duomo on 25th July every year.

  • Visit the tourism board site for more details.


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Tip from tour guide

Joanna

Joanna
Tuscany

Forest of Teso

If you're an adventure lover, you can try exploring the hiking areas near Pistoia. I love hiking in the Forest of Teso, less than an hour from Pistoia in Tuscany. It's a beautiful forest full of light, water, and whispering leaves.

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8. Chiusi

Chiusi is not your usual pitstop as you make your way through the province of Siena in the Tuscan countryside, but it’s a town with plenty of surprises up its sleeves. Once an important Etruscan settlement, legend has it that under Chiusi, you’ll find an extensive network of underground tunnels made and carved by the Etruscans. A small part of it is open to the public, so visit the underground city if you dare. If you’re feeling a little claustrophobic, enjoy the fresh air aboveground as you visit the Cathedral of S. Secondiano, the Etruscan Museum, and the Etruscan tombs, among other attractions. As an avid traveler, I am eager to partake in new experiences and would love to visit the underground tunnel whenever I visit Chiusi.

Good to know:

  • The town’s Cathedral of San Secondiano, initially constructed in the 6th century and subsequently renovated in the Romanesque style, stands as one of Tuscany’s oldest churches. It features beautiful frescoes and an impressive bell tower.

  • Check out the tourism board website for more information.


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9. Montecatini Terme

One of Tuscany’s most famous spa towns, visiting Montecatini Terme is a must if you want to relax on your tour of the Tuscan region. One of the highlights in town is Parco delle Terme spa complex, which is considered one of the best examples of open-air Art Nouveau architecture. Moving on, Montecatini Terme is also home to the Palazzina Reggia, which used to be one of the residences of the powerful Medici family.

Aside from its spas, Montecatini Terme is also a city of fountains. There are several located in the vicinity, including the Fountain Mazzoni near the rail station and the Guidotti Fountain.

Good to know:

  • Montecatini Terme has been a cultural hub, attracting artists, musicians, and writers. It is also known for its annual Montecatini Opera Festival, held from April to October, and features performances by renowned opera singers and musicians in historic venues.


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10. Barga

Nestled in the Apuan Alps, the medieval town of Barga is the beating heart of Serchio Valley. With the high and mighty Pania della Croce looming beyond the town, Barga is often considered as one of the most beautiful communes in all of Italy. Much of Barga remains untouched– it is virtually still stuck in the medieval times with its architecture and age-old traditions and customs. If you’re always excited to discover hidden gems like me, this place is just for you. Narrow streets weave in and out, which makes exploring the town quite an adventure. Sights to see in Barga include Barga Castle, the limestone duomo built over centuries, and Teatro dei Differenti, the premier venue in Barga for performing arts and theater.

Good to know:

  • Due to the significant number of emigrants from Barga who moved to Scotland in the early 20th century, the town is now recognized as the "most Scottish town in Italy."


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11. Massa

Massa Piazza Aranci 02
Source: Photo by Wikimedia Commons user Piergiuliano Chesi used under CC BY 3.0

Another Tuscan town nestled in the Apuan Alps, Massa is slightly less popular than its marble-producing neighbor Carrara, but still brims with a ton of sights to see and activities to do. Spend a day here and you can see the Malaspina Castle (which dates back to the 15th century) and the nearby Church of San Rocco, which houses a crucifix made by none other than Michelangelo. Down at the city center is the piazza, where you’ll find a marble obelisk pointing to the heavens. Other spots to visit include the Cathedral of Santi Pietro e Francesco, Teatro Guglielmi, Marina di Massa, and the Apenninno Tosco-Emiliano National Park.

Good to know:

  • Massa houses several historic churches and one such popular attraction here is the Massa Cathedral, also known as Duomo dei Santi Pietro e Francesco. It's known for its beautiful facade and interior decoration.


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12. Arezzo

Throngs of tourists can drive you mad, so if you want the quintessential Tuscan experience without the large crowds, head to the capital of the Arezzo Province. The city of Arezzo is not for the traveler who wants to check all of the sights in one day. It’s for slow traveling, and rightfully so. What better way to explore its deep treasure chest, which includes attractions and sites such as the Church of San Francesco and the Piazza Grande, where you can even watch a recreation of a medieval joust? Renaissance art also fills Arezzo, making it a perfect companion to Florence, which is about a 45-minute drive away.

Good to know:

  • One of the popular neighborhoods in the city is the historical center of Arezzo with Piazza Grande being the focal point and the venue of “Giostra del Saracino,” a medieval reenactment that’s held here twice a year.

  • For more details, visit the tourism board page.


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13. Island of Elba

Remember when we told you you can board a ferry from Piombino to explore the Tuscan archipelago? Well, make sure to disembark at one point at Elba, the largest island in the group and the third-largest in Italy. In historical records, Elba is best known for being the home of Napoleon in his exile. It was also an Etruscan and Roman stronghold back in the day. But more recently, Elba is known for its sparkling waters and beautiful string of beaches where you can kick back, relax, and enjoy the Tyrrhenian sun. Snorkeling is a top activity here, as Elba is part of the Arcipelago Toscano National Park. That makes it an ideal place for outdoor enthusiasts who’re interested in learning about the area’s marine life. Make sure to visit the small village of Capoliveri while you’re here.

Good to know:

  • The island of Elba is known for its iron ore deposits, which have been used and cultivated since ancient times by the Etruscans and later the Romans. The Elba Museum of Island of Elba Minerals and Mineral Art offers a detailed insight into this part of the island’s history.

  • For more details, check out the tourism website of Elba.


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14. Lucca

For the classic Tuscan experience, make sure not to miss the town of Lucca. It’s often included in the itinerary with heavyweights like Florence with good reason. Sitting on the plain near the foothills of the Apuan Alps, Lucca is home to about 100 different churches. Even if you’re not the religious sort, you’ll enjoy the architecture and the history that surrounds these sites. If there is one church that shouldn’t be skipped, it’s the Duomo, where you can also find beautiful art, including the tomb of Ilaria del Carretto. Archaeological finds also abound in Lucca. You can find some of these treasures at the National Art Gallery, which makes its home in the Palazzo Mansi.

Good to know:

  • The city of Lucca is renowned for its historic walls, built between the mid-1600s and early 1800s. Interestingly, these walls are present even today and are a popular relaxation spot with benches, drinking fountains, games for children, and more.

  • Visit the tourism board website for more information.


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Tip from tour guide

Joanna

Joanna
Tuscany

Palazza Mansi Palazzo Mansi 1 Palazzo Mansi 2

Hidden gem in Lucca - Palazzo Mansi in Lucca, a real Museum-Residence and a remarkable example of a silk merchant’s house.

Between 1686 and 1691, Raffaello Mansi commissioned some renovation works to Luccan architect Raffaello Mazzanti: pre-existent tower houses were connected, while the rooms on the first floor were decorated in sumptuous Baroque style and frescoed with allegorical representations alluding to the glory of the family. Further modernization works were carried out by Luigi Mansi in the 18 century. The building was sold to the State in 1965 and became a National Museum in 1977. The State recovered the original furnishings, frescoes and tapestries on the walls. 

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15. Monteriggioni

The walled city of Monteriggioni is considered as one of the most memorable towns in Italy. A part of the province of Sienna, it dates back to the 13th century as an important fort, which the Sienese used in their war against Florence. The city walls of Monteriggioni are well-preserved, and most distinctive are the 14 towers that circle the entire city, providing different views of Monteriggioni and the neighboring towns and countryside. Dante Alighieri wrote about these towers in his heyday! Reading is my passion, and I would love to read Dante’s work when I visit this beautiful place. The walls are not the only features that date back to the 13th century– most of the buildings here in Monteriggioni are living museums, virtually untouched. If you want to travel back in time, you go to Monteriggioni.

Good to know:

  • A popular attraction, the Museo Monteriggioni in Arme, focuses on the history and weaponry of Monteriggioni. It offers an educational path and walkways along the walls, providing a glimpse into medieval times. Visitors can also try on period armor and handle various types of historical weapons.

  • Check out the tourism board page to lean more about this commune.


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Tip from tour guide

Joanna

Joanna
Tuscany

Monteriggioni Monteriggioni Monteriggioni Monteriggioni

I sometimes stop at Monteriggioni on my way back to Florence since it's cooler and nice to stay outside. When heading to Siena from Florence, or generally from Northern Tuscany, you should definitely stop there for a moment. This small hill town has preserved one of the most iconic medieval walls in Italy.

Monteriggioni was built by the Sienese between 1213 and 1219 for defensive purposes against their greatest rival - Florence. It lies on the medieval pilgrims' route, Via Francigena, and it's still possible to walk along the route. You can cover Monteriggioni to Siena, about 20 km (12 mi), in around four to five hours. Stop for a short break or a dinner and a panoramic walk. You won't regret it!

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16. Pitigliano

Medieval towns come aplenty in Tuscany, but Pitigliano is quite different. It’s carved out of a volcanic rock, which makes for quite an impressive sight as you drive up to the town. Nobody really knows when it was established, but the earliest written records show it was already around in the 11th century as an Etruscan settlement. As such, you can find forms of their ingenuity scattered all over Pitigliano, such as carved channels.

When in Pitigliano, try out the local specialties such as “sfratto,” a biscuit full of surprises and covered in dough. Wash it down with a glass of Blanco di Pitigliano, a crisp white wine made with Tuscany’s Trebbiano Toscano. Afterward, burn all the calories by going on a walking tour. Include the Etruscan walls, the Palazzo Orsini, and the Cathedral of Saints Peter and Paul in your list of stops.

Good to know:

  • Pitigliano boasts a notable Jewish heritage and is commonly known as “Little Jerusalem” because of its meticulously preserved Jewish district and a synagogue.

  • Visit the tourism board for more details.


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17. Viareggio

Tucked between the Tyrrhenian Sea and the marble mountains of Massa-Carrara, you’ll find the lively and coastal town of Viareggio. Here, you can experience a taste of the Italian Carnevale, which is actually what the name Viareggio means. The Carnevale is a month-long event of parties, extravagant and flamboyant costumes, and gigantic floats. Off-season, a trip of Viareggio is mostly spent on the beaches, getting a tan or just simply enjoying the frothy waves of the Tyrrhenian Sea. In my opinion, this place is a haven for beach bummers thanks to its pristine waters. You can see some of the city’s collection of fine art at the Villa Paolina Civic Museum. This is the quintessential resort town in Tuscany, and it has been so for centuries.

Good to know:

  • Viareggio is known for its stunning Art Nouveau (known locally as Liberty Style) architecture. One of the most historic buildings showcasing this architecture is Villa Argentina, featuring ceramic decorations with subtle colors.


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18. Fiesole

Perched on the hills overlooking Florence, Fiesole is a strong contender for the title of the Prettiest Town in Italy. It is said that this was where Leonardo da Vinci first experimented with the concept of flight. The air is different here– fresher, cooler, and crisper, even in the height of summer. The views are scenic and stunning. The ambiance is relatively relaxing compared to the busy streets of Florence. For ages, Fiesole existed as a rival of the Tuscan capital. And so, the magnificence here is quite a thing to behold. Ancient Roman baths and Etruscan walls are scattered all over the commune. The Roman amphitheater is still being used to this day, and the culinary scene offers mouthwatering specialties. Go here on a day trip from Florence, or stay for a night or two and experience what it was like to be a wealthy Florentine.

Good to know:

  • Fiesole houses several historic villas and gardens that are a testament to Tuscan architecture and landscaping. Two of the popular examples include La Villa Medicea a Fiesole, once a summer residence of the Medici family, and the Villa Le Balze, a beautiful villa with Renaissance architecture, now a part of Georgetown University.


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19. Castiglione della Pescaia

Castiglione della Pescaia (more popularly referred to as just Castiglione) is another slow-travel destination in Tuscany. And when you see the sights and stroll the streets of this coastal community, of course you’ll want to take your time. Castiglione was built around an ancient fortress, and so the town unfurls from the hilltop and into the coast, where you can find its more modern side. Stunning beaches abound, but the main attraction is the Diaccia Botrona, a protected area where you can see flamingoes in their pink glory, as well as ducks and mallards swimming and milling about. I feel nature lovers would really enjoy visiting this place.

Good to know:

  • Castiglione della Pescaia is just a five-minute drive away from Diaccia Botrona Nature Reserve, considered the most significant wetlands in Italy. It's known to house a diverse variety of flora and fauna, as well as over 200 species of birds.


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20. Pienza

Pienza, in southern Tuscany, is known for several things. First, it was the birthplace of Pope Pius II (for whom the town is named). Second, it’s one of the prettiest towns in the region because of its Renaissance architecture. Actually, it was built to fit Pope Pius II’s image of the perfect Renaissance town. Considering these things, it’s easy to see why the heart of Pienza was made a World Heritage Site. Third, Pienza has a cheese festival! One of the town’s major products is pecorino cheese, made from milk sourced from Val d'Orcia, which surrounds Pienza. We can go on and on about Pienza, but it’s better if you visit it.

Good to know:

  • Pienza was designated as a UNESCO World Heritage Site in 1996 thanks to its Renaissance urban planning. The town's design and its integration into the surrounding landscape are considered masterpieces of human creative genius.


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Tip from tour guide

Joanna

Joanna
Tuscany

Pienza Pienza Cathedral
Photos and video of Pienza shared by Tuscany tour guide, Joanna.
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21. Montepulciano

Perched 600 meters (nearly 1,969 feet) above sea level, the hilltop town of Montepulciano in the province of Siena is quite a sight to behold. Medieval buildings are scattered all over the commune, and everywhere you look, you’ll most likely find a spot to admire the Val d'Orcia all laid out in front of you. If you’re an eagle-eyed moviegoer, you might also notice Montepulciano as one of the shooting locations for the film New Moon, the second installation in the Twilight saga.

Good to know:

  • Montepulciano is famous for producing Vino Nobile di Montepulciano, one of Italy's most esteemed red wines. Made primarily from Sangiovese grapes grown in the surrounding vineyards, this wine has a rich history dating back to the Etruscans.


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Tip from tour guide

Joanna

Joanna
Tuscany

Montepulciano

Photo of Montepulciano shared by Tuscany tour guide, Joanna.

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22. Volterra

Known as the City of Alabaster, Volterra sits on a mountaintop in the province of Pisa, not far from Florence. Its Etruscan name was Velathri, which became Volterra when the city fell under Roman control. Volterra is famous for its walls and fortifications, not to mention various historic sites like the Roman Theater and the Acropolis. Don’t forget to pick up Volterra-made objects crafted from alabaster, while you’re here. I feel this will make for a perfect souvenir for travelers visiting here.

Good to know:

  • One of the popular attractions in Volterra is the 15th-century Fortezza Medicea, which now houses a prison.


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Tip from Content Creator

Volterra Volterra Volterra
Popularised by the "Twilight" series, this town dates back to the Etruscan times and is filled with gorgeous sites and stunning views. Walk down the cobbled streets and admire the brick buildings on either side.
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23. Portoferraio

The island of Elba is actually quite large (it is, after all, the third-largest in the Tuscan archipelago), so it only makes sense it’s composed of several towns and communes. One of the most scenic is Portoferraio, which usually serves as the main gateway to the rest of the island. Here, you can visit two of the villas where Napoleon lived during his exile. Other sites to see include the Archaeological Civic Museum and the Vigilanti Theatre.

Good to know:

  • The name "Portoferraio" translates to "Iron Port," reflecting its historical importance in iron production.


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24. Impruneta

Festa dell'uva Impruneta
Source: Photo by Flickr user leonardo1971 used under CC BY-SA 2.0

Impruneta is usually not on many tourists’ itineraries, but it’s not because there’s nothing to see here. It’s just one of Tuscany’s many underrated gems. Like most Tuscan towns, it’s unclear when Impruneta was established, but we know Etruscans and Romans did a great deal in developing it. Impruneta is famed for baking terracotta tiles and pots– in fact, the terracotta tiles that crown the Duomo at Florence were made here. Two other pillars of Impruneta culture? Wine, of course, and olive oil.

Good to know:

  • Impruneta has been hosting Festa dell'Uva, Italy's oldest and most celebrated grape festival every September. The festival celebrates the town's wine-making heritage and includes parades, floats, traditional music, dancing, and, plenty of wine tasting.


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25. Massa Marittima

For the unfamiliar, Massa Marittima conjures images of the sea, but the town is, in fact, landlocked in southwest Tuscany. There is that local legend, however, that states that thousands of years ago, the ocean once covered these hills. Nothing’s for sure, but we do know that Massa Marittima has Etruscan origins, is the home of the magnificent Duomo of Saint Cerbenius ( a Romanesque Pisan cathedral), and has a mining museum that takes you deep below the town.

Good to know:

  • One of the most intriguing attractions of Massa Marittima is the 13th-century fresco painting called “Tree of Fertility.” It was discovered inside a public fountain in 2000.

  • Check out the toursim board website for more details.


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26. Prato

When in Tuscany, you should at least spend a full day or two at Prato. Surrounded by the region’s greatest art cities, Prato is itself artistic. The city is well-known for its rich textile industry, which dates all the way back to the Renaissance. You can follow the development of Prato’s textile heritage at the Museo del Tessuto, then go shopping for local fabrics in the many specialty shops scattered around the city. Cap the day off with a visit at Museo Pecci, which houses an impressive contemporary art collection. I would love to visit here with my partner and admire the beautiful art pieces.

Good to know:

  • Prato is renowned for a stunning collection of frescoes by the renowned painter Fra Filippo Lippi. Located in the Cathedral of St. Stephen (Duomo di Prato), these frescoes are considered masterpieces of Renaissance art, showcasing Lippi's exceptional skill in composition, color, and storytelling.


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27. Certaldo

If you plan to make Florence the base of your Tuscan holiday, include the town of Certaldo on your list of side trips. The community bears the traces of numerous conflicts between the region’s ruling families. Two of the most important sites in the town are Certaldo Castello and Certaldo Basso. The city gates are quite riveting as well– one of these entrances to Certaldo bears the Medici coat of arms. Another family, the Albertos, keeps their presence felt after hundreds of years as their former residence, the Palazzo Pretorio, stands.

Good to know:

  • Certaldo is the birthplace of Giovanni Boccaccio, a famous Italian writer and poet. Visitors can explore his house, which is now converted into a museum, and learn more about his life and works through various exhibits and manuscripts.


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Tip from tour guide

Joanna

Joanna
Tuscany

Certaldo

Photo of Certaldo shared by Tuscany tour guide, Joanna.

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28. San Gimignano

Located in the middle of Florence and Siena, you can imagine all the drama San Gimignano has witnessed over the years! But this village shouldn’t be overlooked. This medieval walled village has a lot of things that will pique your interest. For starters, there are the 14 tower houses built by San Gimignano’s most prominent families. There were originally 72. From one of these towers, you can enjoy breathtaking views of the valley. While you’re here, pick up some saffron and bottles of the local white wine called Vernaccia di San Gimignano.

Good to know:

  • The historic center of San Gimignano has been designated a UNESCO World Heritage Site since 1990. The town is known for its well-preserved medieval architecture and urban layout. Popular attractions include the Cathedral of San Gimignano where you can view the 14th-century frescos.


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29. Empoli

Empoli’s football club has been making waves in recent years, but the sports scene isn’t the only thing to check out while you’re in the town. A part of the Florence metro area, you can spend a day at Empoli soaking up the sights and enjoying its most famous landmarks: Piazza della Vittoria, the Modern Art and the Resistance Gallery, and the former home of artist Jacopo Carrucci (more known as Pontormo), one of Empoli’s most famous residents.

Good to know:

  • Empoli is home to a professional football club, Empoli F.C., which competes in the Serie A, the highest division of Italian football. It was founded in 1920 and is nicknamed as Azzurri.


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30. San Miniato

San Miniato al Tedesco (often shortened to just San Miniato) has a network of quiet streets. Explore and you’ll find hidden pockets and corners, as well as some of the town’s most historic sites. There’s Piazza della Repubblica with its painted walls and the red Duomo, covered in bricks and fashioned to suit the Gothic and Renaissance styles. There’s a small museum in San Miniato– don’t overlook it, as it houses several works by important Italian masters such as Verrocchio and Filippo Lippi.

Good to know:

  • San Miniato is renowned as the truffle capital of Tuscany, particularly famous for its white truffles (tartufo bianco).


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31. Mugello

Contributed by Tour Guide, Joanna

Source: Joanna

Have you ever been to the Mugello region in Tuscany? During my last hike, I had the opportunity to visit the town of Vicchio in Mugello and see the house where Italian painter and architect Giotto was born.

Situated on the lovely hill of Vespignano, just below the Church of San Martino, this old and simple medieval building has been altered more than once over the centuries. After a year-long dispute, it is now considered the real birthplace of Giotto di Bondone (1267 - 1337). The house was transformed into a museum dedicated to this great artist who operated the revolution in European art.

Mugello offers a lot of attractions aside from the picturesque town of Vicchio. On the trail, there’s a medieval bridge, Ponte di Cimabue, a legendary spot where Italian painter Cimabue had encountered young Giotto. Nearby, it’s also possible to explore the birthplace of another Italian painter, Beato Angelico.

32. Bagno Vignoni

Contributed by Tour Guide, Joanna

Bagno Vignoni
Source: Joanna

Visit Bagno Vignoni during your stay in Tuscany. We visit the village to try local food, relax in the spa (for a fee), or take a picture with the thermal tub in the background. In Bagno Vignoni, there are about 30 registered inhabitants, 10 cats, including a very affectionate black one, and a colony of frogs. There are many hotels (some with thermal day spas) and restaurants.

Check out some other interesting facts about the village:

  1. The Etruscans, the Romans, and then the pilgrims of Via Francigena enjoyed the spa greatly. In fact, what we see today in the small town are mostly medieval remains.

  2. Santa Caterina of Siena had immersed herself in the hot springs to heal self-inflicted flogging wounds.

  3. Even doctors, such as Lorenzo the Magnificent and Pope Enea Piccolomini, visited this place.

  4. Tarkovskij filmed scenes from the movie Nostalgia here in 1982.

  5. You can find four medieval mills here, and a drainage tub where, every now and then, some daredevil tries to take a bath.

  6. The area is spectacular and you can do a lot of trekking, ride a bike, enjoy other hot springs (some for free), and visit nearby places such as Pienza, Montalcino, and Montepulciano.

33. Castelvecchio, Pescia

Contributed by Tour Guide, Joanna

Source: Joanna

I went hiking in Pesciatina Switzerland, Castelvecchio, and discovered a different side of Tuscany. Visit the place if you admire beautiful landscapes and sceneries. You can find vast clearings with gray rock formations, forests, small rugged villages, and glimpses of the Apenine Mountains. The municipality is also home to Pieve di Castelvecchio. This church has curious details on the facade, featuring masks and a relief with people hugging and smiling.

34. San Quirico d’Orcia

Contributed by Content Creator, Francesca

Source: Francesca

Group of cypresses, cypresses in a row, cypresses standing alone in the countryside—cypresses are the quintessence of Tuscany! And the comune of San Quirico d’Orcia is the best place to see them.

In the wheat fields close to San Quirico d'Orcia you can find two incredible spots to take pictures of cypresses:

  • Polygonal group
  • Circular group

Search for “cipressi di San Quirico d'Orcia” on Google Maps, then leave your car in one of the two small rest stops along the road and follow the dirt road that leads to the first group visible from the road.

35. San Donato in Poggio

Contributed by Tour Guide, Joanna

Source: Joanna

While Monteriggioni has now become a hyper-touristic place, San Donato in Poggio, 20 km (12.4 mi) north, has preserved its authentic character of a small town sleeping between the sweet hills of Chianti.

The walls here are two centuries old! The town has two doors, a main square with a beautiful building, a church, and a Romanesque meadow nearby. In the summer, it’s nice to dine in one of the local restaurants or take a late afternoon stroll in the area. There’s also no shortage of glimpses and stunning views all around, and time seems to stop here as it happens often in some parts of Tuscany.

Soak in all the history and high culture

Carrara101
Source: Photo by Wikimedia Commons user g.sighele used under CC BY 2.0

As you travel through Tuscany, you’ll experience its distinct culture and heritage and find out why it’s often said it is its own country. As a traveler, you’ll never run out of options as there are several things to do here. As a bonus, you’ll get your fill of medieval cities and towns, Italian Renaissance masterpieces, and bottles upon bottles of outstanding wine. Life is beautiful in Tuscany, indeed.

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Vanna is born and raised in the Philippines and describes herself as a local tourist-- she's made it her mission to see as many of the country's 7,000+ islands. But that doesn't mean she's not...Read more

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