Undulating hills, manicured rows of cypress trees, and endless wine groves — it’s easy to see why Chianti is such a sought-after destination. The region is arguably Italy’s most famed wine district. And a simple mention of the region triggers instant connotations of vast Tuscan countryside, with thriving gastronomy and natural beauty.
Situated between Florence and Siena, this region of Tuscany spans approximately 100 miles. And with everything considered, it’s hardly surprising that there are many things to do in Chianti, Italy. The region is a gold mine for discerning and solace-seeking travelers. Here are the top contenders for your itinerary.
1. Wine Tasting
Wine is at the pulse of Chianti’s culture. For knowledgeable enthusiasts, the viticulture and prized bottles have likely already inspired your visit. But for those unaware of its affinity for wines, here’s your sign. Tasting tours are the most famed experiences in Chianti. In fact, the best time to visit Tuscany coincides with the grape harvest season; do with that what you will.
The wine itself has lots of interesting characteristics, including distinct earthiness and cherry notes. It must also contain at least 70% of Sangiovese grapes to retain its location-specific status. Try different samples of the region’s bottles, riding a deliciously acidic and ruby red wave.
2. Road Trip Chianti’s Towns
Chianti is a beautiful region for road trips. The scenery, the sun, and the culture — it all combines to curate dreamy slow-travel. The best route to explore Chianti’s best towns is via Chiantigiana. This 69 km journey connects Florence with Siena, passing gorgeous towns like Greve, Castellina, and Gaiole.
Rent a vehicle from Florence airport or hire a classic Vespa from a local company. Take it steady, and ideally, stretch out the experience over a few days.
3. Take a Cooking Class
In Chianti? Fresh produce matters, and that shows in its dishes. Still, the cuisine can feel like a fleeting opportunity for travelers exploring the region, so why not take some dishes home with you? Taking a cooking class is a great addition to your itinerary.
Learn how to make pasta from scratch, throw together a perfect pizza, or concoct a mind-blowingly tasty tomato sauce. Cooking experiences are easily booked through third-party operator sites, like Viator or GetYourGuide.
4. Olive Oil Tasting
The savviest readers will have spotted an olive-sized hole in these suggestions. Chianti isn’t just associated with famous Italian wine; the region is cloaked in patchwork groves of olives and grapes. These saltier fruits are harvested each fall and transformed into liquid gold: Tuscan oil.
Many oil tastings are hosted alongside wine-based experiences. For instance, Ulivello offers homemade oils and wines in a 19th-century villa setting, while Terre di Melazzano runs similar sessions from a farm outside Greve.
5. Soar in a Hot Air Balloon Tour
Soaring through the skies is enough to instill excitement in the most stoic of travelers. Yet add the serene landscape of Chianti into the mix, and you immediately amplify the novelty. A hot air balloon tour feels peaceful and unintrusive. Rather than speeding by, the balloon provides a gentle observation point, granting passengers a serene seat to admire rolling hills and red-brick estates. That view is unbeatable.
Spot castles, olive groves, and villas from above. These experiences are easily booked through third-party operators, and flights typically last an hour. The best packages incorporate a sunrise or sunset, and ideally a tipple to celebrate on your return. Prosecco, anyone?
6. Explore Art in Florence
Amidst the debate over where to stay in Tuscany, there is always one destination mentioned repeatedly: Florence. While technically located outside Chianti’s regional boundaries, visitors should allow themselves to be swayed by the temptation of a detour. Most visitors will fly into Florence Airport to start their trip, so the city is easily accessible. The Tuscan capital is just 30km north of Greve, a wine town many deem Chianti’s gateway.
Take a break from the hills and wine groves. Spending a day in Florence to explore its art history is a cultured addition to any Chianti itinerary. Admire its Renaissance cityscape from Brunelleschi’s Dome, tour Palazzo Vecchio, and visit a piazzale dedicated to Michelangelo.
7. Spend a Day in Siena
It would be an abomination to mention Florence and omit Siena. The city is the capital of its (same-named) province, and has a UNESCO-protected center teeming with medieval architecture. Walk the shell-shaped Piazza del Campo and squeeze down narrow streets like Via di Città.
Again, while Siena might not technically fall into Chianti’s region, it holds poignant day-trip potential. Situated just south of Chianti’s borders, adding a Siena trip to your itinerary is certainly feasible. Consider adding Val d’Orcia in, too; this aesthetic region is the postcard image everyone envisions when visiting Tuscany. Besides, the two are only an hour apart by car.
8. Hunt For Truffles
Think of Chianti, and tracking down edible fungi might not immediately spring to mind. However, truffle hunting is a fast-growing activity for tourists, especially given the spurred movement of farm-to-table dining. These fungi vaguely resemble conkers, only with bobbly coats. Dark and solid, with hard shells, these are a distinctive-looking natural product.
Chianti has many operators offering guided truffle hunts. And while it is a year-round activity, the season of your visit will dictate what variations are available. Black truffles are rife through spring and summer, while fall produces prized white truffles. Surprisingly, sharp-eyed hunters even find variations of this fungus throughout winter, with mild marzuolo truffles re-entering the scene. This activity is rewarding for foodies, but equally incorporates Chianti’s culture and cuisine. Consider it a winning recommendation.
9. Walk the Chianti Sculpture Park
At first glance, Chianti seems void of prevalent artwork. Unlike the density of art galleries, sculptures, and frescoes in Florence or Siena, this region is centered around beautiful countryside. But that doesn’t mean it’s impossible to scope out manmade beauty — you just need to know where to look. Luckily, the Chianti Sculpture Park is one such spot.
The park hosts dozens of sculptures across 17 acres of precious oak woodland. Amazingly, these pieces of artwork were created by artists from 25 different countries and 5 continents. Its goal? To protect the intersection of art and nature.
Spot multi-colored cows by Singaporean Vincent Leow, a “crashed” rainbow by Italian Federica Marangoni, and twisted human statues by American Neal Barab. As of 2025, there’s a €10 entrance fee for adults. Chianti Sculpture Park is great value and full of contemporary surprises.
10. Tour Medieval Castles
When you think of Chianti, grandeur instantly springs to mind. In Tuscany, luxury villas are awe-inspiring. These traditional buildings often overlook (or own) acres of olive or grape groves. And many come with facilities like private pools, some with infinity designs.
No matter how stunning your accommodation is, though, prepare to put it to shame. The region has a rich assortment of medieval castles, each featuring mind-blowing architecture and fascinating tales. To embrace one of the most historic things to do in Chianti, Italy, consider one of the following:
- Brolio Castle: A property that dates back to the Middle Ages and was home to Baron Bettino Ricasoli (the founder of Chianti’s Classico region).
- Volpaia Castle: A medieval castle and village with a knack for wine-making and a history of strategic defence.
- Vicchiomaggio Castle: A 15th-century castle that once hosted Leonardo da Vinci.