20 best things to do in Tuscany, Italy

Tuscany is the region people often picture when they daydream about Italy. This is where you'll find rolling hills lined with cypress trees and vineyards stretching to the horizon. But it’s more than just a postcard view. This is the birthplace of the Renaissance, where art, science, and architecture changed the course of European history. It has a character that feels different from the rest of the country. Here's our list of the best things to do in Tuscany, from the well-known stops to the hidden gems.

1. Chianti vineyards and wineries

Between Florence and Siena, the Chianti region of Italy is known for rolling hills covered with vineyards, old estates, and medieval castles that still house working wineries. The best-known wine here is Chianti Classico, marked with the black rooster seal, but you’ll also come across Super Tuscans and Riservas aged in cool stone cellars.

A typical visit might start with a walk through the vines as winemakers explain how Sangiovese grows in this climate, followed by tastings paired with pecorino cheese and cured meats. Chianti has had strict wine regulations since 1716, making it one of the oldest recognized wine regions anywhere.

Visit in September if you want to catch the grape harvest and local festivals, or plan your Italy itinerary for spring when the vineyards are green and full of wildflowers.
 

2. Truffle hunting

Truffle hunting is a very Tuscan experience, with handlers and their dogs leading you through oak forests in search of prized fungi. The hills around San Miniato are famous for white truffles, which appear from September to December, while black truffles are more common in summer.

Truffle hunters, called tartufai, often come from families who have been doing this for generations, and their Lagotto Romagnolo dogs are trained to sniff out even the smallest trace underground.

After the hunt, the day usually ends with a meal where truffles are shaved over pasta, eggs, or cheese. What better way to plan your trip to Italy than with freshly made meals?

The combination of the region’s soil and forest trees makes it one of the best places for truffles. Hunts are run with the proper permits, and any truffles you take home come with an authenticity certificate.
 

3. Olive oil tasting

In autumn, the olive harvest takes over much of Tuscany. From October to November, freshly pressed “olio nuovo” is available, a green, peppery extra virgin oil with a short seasonal window.

Tastings often introduce you to local olive varieties like Frantoio, Leccino, and Moraiolo, and you’ll get a sense of how traditional cold-pressing methods compare with modern techniques.

During a guided tasting, you warm the oil in your hand, slurp it to release the flavors, and identify notes like grass, artichoke, or almond. Some mills still use stone wheels, while others rely on centrifuges.

Tastings often include bruschetta drizzled with new oil, shops selling oil-based soaps and creams, and sometimes programs where you can adopt an olive tree and receive oil from that year’s harvest. Many shops in Florence will also stock these items (olive oil is an important ingredient in most of the best foods in Florence).

4. Cortona

Cortona sits high above the Val di Chiana at about 2,000 feet (600 meters), with views stretching out toward Lake Trasimeno.

The town became well known after Under the Tuscan Sun, but it still feels quieter than San Gimignano and keeps its Etruscan and medieval character. Walking through town, you’ll come across steep cobblestone streets, Renaissance churches with works by Luca Signorelli and Fra Angelico, and the MAEC museum (which has standout Etruscan bronzes like the famous chandelier decorated with Medusa heads).

On Saturdays, Piazza Signorelli fills with a market selling fresh produce, antiques, and leather goods. Just outside town you can visit old hermitages in the hills and the strikingly geometric church of Santa Maria delle Grazie al Calcinaio.

In summer, the Tuscan Sun Festival brings international musicians to Cortona, while autumn is when you’ll find mushroom foraging and wine harvest celebrations. No matter the time of year, you could easily spend a 2-week Italy itinerary in Tuscany alone.

5. Monti dell'Uccellina (Maremma Regional Park)

Maremma Regional Park covers about 15 miles (25 kilometers) of wild coastline with beaches, pine woods, and marshes. It is still traditional ranching land, where local cowboys, known as butteri, herd semi-wild cattle. This is by far one of the best things to do in Tuscany.

The park is also a major bird habitat, with flamingos, herons, and birds of prey. Trails run past medieval watchtowers, the ruins of San Rabano Abbey, and quiet coves that you can only reach on foot. 

Deer, wild boar, and porcupines are common, and the distinctive white Maremmana cattle graze the meadows by the sea. The visitor center in Alberese handles entry, since cars are not allowed inside. From there you can set out on easy beach walks, longer hikes into the hills, horseback rides along the shore, or canoe trips through the lagoons.
 

6. Montalcino

Montalcino is known for Brunello, a red wine made from Sangiovese grapes that is aged for years before release. The town overlooks the Val d’Orcia, and its 14th-century fortress has panoramic views as well as a wine bar featuring local producers. A visit here is one of the best things to do in Tuscany.

The narrow streets lead to family-run trattorias where you can try pici pasta with wild boar ragu, a local favorite.

Every February the Benvenuto Brunello festival introduces new vintages. The surrounding hills are covered with vineyards, home to more than 200 wineries.

Some are small family estates, while others, like Biondi-Santi, are historic names connected to the origins of Brunello in the late 1800s. Many wineries welcome visitors for tastings or cellar tours, often by appointment. If you are here in October, you may also find opportunities to join in the grape harvest. It's a great stop on any Italy wine tour.

7. La Verna Monastery

High in the Casentino forests, La Verna is known as the place where St. Francis received the stigmata in 1224. The monastery complex includes chapels decorated with della Robbia’s glazed terracotta works that trace scenes from Francis’s life.

You can still see the stone where he slept and the cliff where he went for prayer and reflection. The monastery library holds medieval manuscripts and early printed books, and the monks here continue centuries-old traditions of welcoming visitors.

Trails through the surrounding beech and fir forests lead to hermit caves used by Franciscan monks, and the morning fog often makes the place feel even more secluded. Visitors can join sung vespers, stay in simple pilgrim rooms, and pick up liqueurs, honey, and religious items made by the community in its historic pharmacy. This is one of the most relaxing things to do in Tuscany.
 

8. Uffizi Gallery, Florence

The Uffizi is one of the most important places to see Renaissance art, housed in a 16th-century palace built for the Medici family.

This is one of the best museums in Florence. Inside are works by Botticelli, Leonardo da Vinci, Michelangelo, and Raphael, among many others.

Botticelli’s Birth of Venus and Primavera are highlights, while Leonardo’s Annunciation shows his groundbreaking use of perspective. 
The museum’s rooms trace European painting from medieval panels to the height of the Renaissance, and the Vasari Corridor—a secret passage once used by the Medici—contains hundreds of self-portraits. It’s best to reserve tickets in advance, no matter how many days in Florence you have.
 

9. Alpi Apuane trails and Carrara marble quarries

The Alpi Apuane rise sharply from the Tuscan coast and are famous for their marble quarries, which supplied the stone for Michelangelo’s David and many Roman monuments.

You can take quarry tours that go into vast chambers where marble is still cut today, or visit the Marble Museum to see how techniques have changed over time. Sculptors in the area still use traditional carving methods, and you can watch them at work.

Hiking trails wind through the mountains, passing marble debris fields and leading to peaks with views of both the Mediterranean and the distant Alps. The nearby village of Colonnata is known for lardo, a cured pork fat aged in marble basins since Roman times.

If you want something more active, there are via ferrata climbing routes, underground rivers to explore, and guided quarry tours.  In August, full moon tours give the mountains an almost glowing appearance under the night sky.
 

10. Siena

Siena feels like stepping straight into the Middle Ages, with everything centered on the shell-shaped Piazza del Campo.

Twice a year, the square is covered in sand for the Palio horse race, when the city’s 17 contrade (neighborhoods) fiercely compete, each with its own colors, flags, and traditions going back to the 1200s.

The black-and-white striped Duomo is worth a slow visit, not just for its Gothic and Romanesque architecture but for its marble floor. Most of the time it is protected, but for a couple of months each year the detailed biblical scenes are revealed.

If you can manage the 400 steps up the Torre del Mangia, you’ll see a wide view of the rooftops and vineyards beyond. Beneath the city, old aqueducts and cisterns once supplied Siena’s water and can still be toured today. Between walks, try panforte, a dense spiced cake, ricciarelli almond cookies, and a glass of Chianti Colli Senesi. 
 

11. Piero della Francesca's works in Arezzo

In Arezzo, the Basilica of San Francesco holds Piero della Francesca’s fresco cycle Legend of the True Cross. It traces episodes linked to the wood of Christ’s cross, painted with perspective and light effects that were well ahead of his time. The Dream of Constantine is especially striking for its night scene.

The town’s civic museum shows more of his work alongside paintings by Vasari and fine medieval goldwork. In nearby Sansepolcro, Piero’s birthplace, you can see his famous Resurrection, once called one of the greatest paintings ever made by Aldous Huxley.

If you are there on the first weekend of the month, Piazza Grande fills with an antiques market, and is a great thing to do in Tuscany while you are here. Arezzo also hosts the Giostra del Saracino, a jousting tournament that brings the streets to life with costumes, parades, and competitions.
 

12. San Gimignano

San Gimignano is known for its medieval towers. Only 14 remain from the original 72, but they still shape the skyline in a striking way. They were built by wealthy families in the 13th century as both defenses and status symbols.

You can climb Torre Grossa, the tallest of them, for views of the surrounding hills toward Volterra and the Apuan Alps. Inside the Collegiate Church, the walls are covered in frescoes, including New Testament scenes painted by Ghirlandaio opposite Old Testament stories.

The town is also associated with Vernaccia di San Gimignano, a dry white wine with a long tradition. For something different, stop by Gelateria Dondoli in Piazza della Cisterna, where flavors use local ingredients like saffron or Vernaccia itself. This is one of the best day trips from Florence you can take.

13. Pisa

Most people head to Pisa for the Leaning Tower, but the Campo dei Miracoli is a whole square of landmarks worth your time.

Alongside the tower are the Duomo, the Baptistery, and the Camposanto cemetery, all within one UNESCO site. The tower leans at just under four degrees today, held in place by careful engineering. Legend has it Galileo tested theories of gravity from the top, which you can still climb with a timed ticket. 

The Duomo’s bronze doors by Bonanno Pisano later influenced church entrances across Europe, while the Baptistery is famous for its acoustics, where sounds seem to stretch on forever.

The Camposanto is home to frescoes like the Triumph of Death, one of the most striking depictions of the plague from medieval times. Away from the square, you can see Keith Haring’s bright mural “Tuttomondo” or wander the city’s botanical garden, which has been growing since the 1500s. It is a must for any Tuscany itinerary.

14. Pienza

Pienza feels like a Renaissance vision turned into a real town. Pope Pius II redesigned his birthplace to reflect ideals of symmetry and proportion, creating a main square framed by the cathedral, papal palace, and town hall. Instead of the traditional east-facing layout, the cathedral was built to bring in light from the Val d’Orcia, with views of rolling fields through its windows.

Pienza is also known for pecorino cheese, which comes in varieties aged in ash, caves, or infused with truffle. In September, a festival celebrates this tradition with medieval costumes and a cheese-rolling competition through the streets.

The gardens of Palazzo Piccolomini overlook the valley and are especially striking at sunset, with views stretching across fields and cypress-lined roads. It's a fantastic thing to do in Tuscany. 

15. Lucca city walls

Lucca is surrounded by Renaissance walls that still stand in full and have been turned into a tree-lined pathway around the city. At just over 2 miles (4 kilometers) long, they’re wide enough for cyclists, runners, and families out for a walk, with rooftop views across the historic center.

Inside, the medieval streets lead to hidden piazzas and churches, including Torre Guinigi, a tower topped with oak trees where you can climb for views across the city.

The oval-shaped Piazza Anfiteatro traces the footprint of a Roman amphitheater, now ringed by colorful houses, shops, and cafés. Music fans may want to stop at the Puccini museum in the composer’s former home, while summer brings open-air opera performances around town. Unlike Pisa or Florence, Lucca has fewer day-trippers. 
 

16. Thermal springs (Bagno Vignoni and Saturnia)

Tuscany is full of natural hot springs, many used since the Etruscans for their mineral-rich waters.

Saturnia’s Cascate del Mulino is one of the best known, with warm 98°F (37°C) water flowing into tiered limestone pools where you can soak for free year-round. It is especially enjoyable in winter when the cooler air makes the steam more dramatic (see our guide to the best time to visit Italy).

Bagno Vignoni is completely different. Instead of paving stones, the village square is taken up by a large steaming pool, a sight that has defined the town for centuries. St. Catherine of Siena is said to have bathed here.

The waters contain sulfur and minerals long believed to help with skin, joint, and respiratory conditions. Around both places, modern spas give you the chance to spend a day between historic pools, mud treatments, and massages.
 

17. Montepulciano

Montepulciano is set high on a limestone ridge and is best known for its Vino Nobile, a red wine that has been made here for centuries. The main street climbs steeply from the old gates up to Piazza Grande, passing Renaissance palaces and small wine shops along the way.

Beneath the town, there’s a network of underground cellars carved into the rock, some with origins as far back as Etruscan times. Cantina Contucci is a good place to see this history in action, with wine still aging in the same vaulted spaces that have been used for generations.

If you visit in July, the Bravio delle Botti brings the streets to life as teams roll heavy wine barrels uphill to the main square. Just below town, the Tempio di San Biagio stands on its own among cypress trees and vineyards.

When you sit down for a meal, try the local hand-rolled pici pasta, often served with wild boar ragù, alongside a glass of Vino Nobile. From the edges of town, you can look out toward Monte Amiata, Val d’Orcia, and Lake Trasimeno. 
 

18. Val d’Orcia countryside

The Val d’Orcia is the landscape many people imagine when they picture Tuscany. Rolling farmland, lone cypress trees, and winding roads spread out around hill towns like Pienza, Montalcino, and San Quirico d’Orcia.

The area’s clay soil has also created the crete senesi, a rugged, pale terrain that looks almost lunar near Asciano. Small chapels and farmhouses dot the valley, with the Cappella della Madonna di Vitaleta being one of the most photographed.

The region is famous for Brunello di Montalcino, Vino Nobile di Montepulciano, and pecorino cheese, so food and wine are central to any visit. Each season changes the look of the valley, from spring’s green fields to autumn’s colorful vines.

This is a fantastic place to plan an Italy road trip. You can also see it all from above on a hot air balloon flight.

19. The Maremma coastline

In the southwest, the Maremma is Tuscany’s wilder coast, with long Italy beaches, pine forests, and wetlands that attract plenty of birdlife, including flamingos.

The Argentario peninsula is linked to the mainland by sandy strips that form lagoons, and the harbors of Porto Santo Stefano and Porto Ercole still feel like working fishing towns even though yachts dock there too.

Feniglia beach runs for almost four miles (6 km) and is great for long walks, horseback rides, or water sports. The coast also carries reminders of its past, with Spanish forts on Argentario and Etruscan remains near Talamone. Local seafood is another reason to visit, from cacciucco fish stew to pasta with sea urchins
 

20. Etruscan sites (Populonia, Roselle, Chiusi)

Tuscany was shaped long before the Romans, and these three towns show how advanced the Etruscan world was. Populonia looks out over the sea and once played a central role in iron smelting, with tombs ranging from simple graves to grand burial mounds filled with jewelry and weapons.

Roselle’s city walls and amphitheater remain clear examples of early planning, and ongoing digs have uncovered mosaics and bath complexes. In Chiusi, you can walk through underground passageways that connect painted tombs, where carefully placed lighting brings out colors that have survived for centuries.

The local museums bring all of this together with displays of sarcophagi, bronze mirrors, and the distinctive canopic jars with sculpted heads. These places tend to be quieter than Roman ruins, especially in spring when wildflowers grow across the ancient streets. Guided visits help explain how Etruscan traditions fed into Roman culture.
 

21. Volterra

Volterra has been continuously lived in for more than 3,000 years, and you can still see traces of each period as you explore. Alabaster carving has been part of the town since Etruscan times, and workshops along the narrow streets still produce it today.

The Guarnacci Museum is worth visiting for its collection of Etruscan pieces, including the elongated bronze figure called the “Evening Shadow” and hundreds of carved urns.

The ruins of a Roman theater remain impressive, and summer performances are sometimes staged here. Above the town stands the Medici Fortress, now used as a prison. On the edge of Volterra, the cliffs known as Le Balze continue to erode, gradually taking pieces of the old town with them.

Food here is hearty, with wild boar, truffles, and pecorino cheese appearing often on menus. While the town’s moody atmosphere has even inspired vampire stories, the sunsets are what most people remember, with wide views across the hills to the sea. 

Ready to plan your trip? See our guide to making the best 10-day Italy itinerary to spend your time wisely.