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. Alternatively, you can take it slow and take a casual stroll along the river, then just stop by any shop, restaurant, or site that attracts your interest.

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.

3. Piombino

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. 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.

4. Florence (from USD 143.0)

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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. 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.

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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.

6. Montalcino

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.

7. Pistoia

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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. 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!

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.

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.

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. 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.

11. Massa

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.

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.

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. Make sure to visit the small village of Capoliveri while you’re here.

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.

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! 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.

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.

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. 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.

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.

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.

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.

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.

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.

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.

24. Impruneta

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.

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.

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.

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.

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.

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.

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.

Soak in all the history and high culture

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 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.