Chianti Wine Tour from Florence

Walking Tour

6 hours

Florence

Uncork a bottle of Chianti among castle walls and vineyard roads, with expert sommeliers who reveal the deeper traditions behind Tuscany’s famous wine culture.

Castle Walls and Cellars Step inside a private castle estate and taste Chianti at its source.
Roads Through Chianti Travel vineyard-lined hills with seamless service from Florence included.
Machiavelli’s Tuscany See the landscapes that shaped “The Prince” and Renaissance thought.
Wine Without Pretension From curious beginners to experts, every tasting opens new perspectives.
Flavors of Tradition Pair Chianti wines with Tuscan dishes rooted in local family customs.
Beyond The Cities Connect with the region through stories, landscapes, and working traditions.

Led by Experts, Shaped by You

Explore with an expert guide who responds to your questions, your interests, and your pace. Reveal layers of meaning most visitors miss—go from seeing to understanding.

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The road between Florence and Siena tells the story of Tuscany through vineyards, olive groves, and hilltop villages shaped over centuries. Chianti is more than a wine region. It is a landscape where agriculture, history, and everyday life still move together. Rolling countryside replaces the rhythm of the city as Tuscany begins to unfold more slowly.

Led by your Expert sommelier, the experience explores the heart of the Chianti Classico region. In San Casciano Val di Pesa, vineyard-covered hills stretch outward in every direction, while medieval streets and historic villas reveal the deep connection between the land and its wines. This countryside has carried Etruscan, Roman, and Renaissance influences for generations.

Sant'Andrea in Percussina, your next stop, offers a quieter lens into Tuscan history. Niccolò Machiavelli lived here during his exile from Florence, writing parts of “The Prince” among these same rolling hills and agricultural landscapes. What happens when political ambition gives way to rural isolation? The atmosphere of the village still invites reflection.

The experience continues at Castello della Paneretta, a private estate centered around an ancient 13th century castle. Historic rooms, old cellars, and vineyard views reveal how deeply wine traditions remain tied to family, place, and heritage in Tuscany. The castle still feels connected to the rhythms of the countryside surrounding it.

Inside the historic cellars, your sommelier guides a tasting of three Chianti wines paired with Tuscan specialties including cured meats, cheeses, bruschetta, Ribollita, cantuccini biscuits, and Vin Santo del Chianti Classico D.O.C. Each pairing connects flavor to local tradition, revealing why Chianti became one of Italy’s most celebrated wine regions.

Returning toward Florence, the hills carry a different meaning. Beyond the vineyard postcard exists a living landscape shaped by generations of farming, storytelling, and winemaking traditions. Tuscany reveals itself here not only through what you taste, but through the deeper culture behind every glass.

From iconic landmarks to tucked-away local favorites, these are the places you’ll explore and experience firsthand with your Expert.

San Casciano Val di Pesa
Sant'Andrea in Percussina
Castello della Paneretta

Here’s a look at what your tour covers, plus anything you’ll want to consider arranging separately, so you can plan with confidence.

Included

English-speaking expert guide
Tours led in English, offering you unbroken understanding throughout.
Intentionally sized groups
A smaller group means more time for conversations and questions.
Tickets and entrance fees
All entry tickets included (unless clearly stated otherwise).
Headsets
Headsets are included on tours that need them, so every word can be heard.

Not Included

Gratuities

We encourage tipping as a way to thank your guide after your experience.
Food and drink

Refreshments are only included during a tour when clearly noted.
Transportation to and from the meeting point

Unless noted, pre- and post-tour transport isn’t included - this service can be added by request.
Hotel pickup or drop-off

Unless noted, travel to or from accommodation isn’t included - this service can be added by request.

Some helpful advice for getting the most from your experience, from practical prep to small on-the-day tips.

Dos:

Wear comfortable footwear
Check the weather and dress appropriately
Bring a bottle of water (no glass)
Feel free to ask your Expert anything

Don'ts:

Bring firearms or weapons
Bring sharp objects (e.g. knives, swiss army knives, switchblades, hiking sticks)
Dress inappropriately to enter religious sites or sacred monuments

Any questions? You can always contact us.

Yes, of course, you can purchase what you’d like during your tour, though Context is not responsible to the shipping and safe delivery of the items back to their destination.

No, for insurance reasons, the expert cannot be in the car with you so we cannot organize this. You are more than welcome to update the pickup location if interested.

While families and travelers of all ages are welcome, please keep in mind that this itinerary features wine tastings. We are happy to coordinate with the venues to provide non-alcoholic refreshments for younger guests, but the primary focus of the experience is adult-oriented. The day is also quite comprehensive and involves a significant amount of walking at an active pace. While the final decision rests with the parents, we recommend this tour for children who are accustomed to longer excursions and more mature environments.

We are happy to consider alternative pickup locations on a case-by-case basis. If your accommodation is outside central Florence, please provide the details at checkout. We will contact you to discuss the logistics and any potential additional transportation fees that may apply.

Yes, we can certainly arrange a meeting point in Chianti. Please specify this preference during checkout. Please be aware that because our guides travel from Florence, the private car service remains reserved for their transit; therefore, meeting in Chianti does not result in a price reduction. Additionally, the start time in Chianti may be slightly later than the standard Florence departure.

Certainly. If you wish to remain in Chianti at the end of the day, please let us know at checkout so we can coordinate accordingly. Since our guides are based in Florence, the car service is still required for their return journey. Choosing this option may result in the tour concluding slightly earlier than scheduled, as it will not include the final drive back to the city.

Please be advised that this tour involves a 1.5 km walk across varied and challenging terrain, including cobblestones, hills, and natural surfaces like sand and cliff paths. Accessing the historic cellars requires navigating 20 steps. While we can accommodate accessibility needs with certain modifications, we recommend contacting us in advance to ensure the route is suitable for your specific requirements.

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Join passionate experts on intimate walking tours that reveal a city’s unique stories, spark conversations, and leave you seeing the world—and yourself—a little differently.

Structured, never scripted

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Experts, not guides

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