Chianti Wine Tour from Siena

Walking Tour

6 hours

Siena

Taste Chianti wine among castle estates and vineyard roads, guided by a sommelier who connects each glass to Tuscany’s deeper traditions

Castle Doors and Cellars Enter a historic estate and taste Chianti where it’s still produced today
Through Chianti Hills Move easily across vineyard-lined roads with transport arranged from Siena.
Machiavelli’s Exile Stand in the landscape that framed The Prince and its enduring ideas.
Wine Theory, Made Clear Whether new or knowledgeable, each tasting builds your understanding.
Tuscan Table Traditions Experience pairings rooted in local recipes and seasonal ingredients.
Countryside Life Explained See beyond the scenery into the people and practices shaping it.

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 Siena and Florence reveals Tuscany at its most enduring—vineyards, olive groves, and hilltop villages shaped over centuries. Chianti is more than a destination for wine. It is a working landscape where agriculture, history, and daily life remain deeply intertwined. Leaving the city behind, the pace softens, and the countryside begins to speak for itself.

Led by your Expert sommelier, you’ll explore the heart of the Chianti Classico region, where vineyard-covered hills stretch in every direction. In San Casciano Val di Pesa, medieval streets and historic villas offer insight into how land, labor, and legacy have long defined Tuscan wine culture. Here, layers of Etruscan, Roman, and Renaissance influence still quietly shape the terrain.

In Sant’Andrea in Percussina, the story shifts inward. This is where Niccolò Machiavelli spent his years in exile, drafting parts of The Prince while surrounded by the same agricultural rhythms you see today. The village invites a different kind of reflection—on power, perspective, and the unexpected intersections between political thought and rural life.

At Castello della Paneretta, a private estate anchored by a 13th-century castle, the experience becomes tangible. Stone walls, historic rooms, and aging cellars reveal a continuity of tradition that still defines winemaking here. This is not a staged setting, but a place where family, land, and craft remain closely linked.

Within the cellars, your sommelier leads a guided tasting of three Chianti wines, each paired with Tuscan specialties—cured meats, cheeses, bruschetta, ribollita, cantuccini, and Vin Santo del Chianti Classico D.O.C. Each pairing deepens your understanding, connecting flavor to place and tradition to technique.

As you return toward Siena, the landscape begins to read differently. What first appeared as postcard scenery now carries context—shaped by generations of growers, thinkers, and artisans. Tuscany reveals itself not only in what you taste, but in the stories that give each glass its meaning.

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 this tour, though remember than Context is not responsible/tied 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 Siena, 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 Siena, 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 Siena, 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

Your interests guide your Expert, leading to stories and perspectives that matter to you.

Crafted for conversation

With ten or fewer guests, ask questions, engage with your Expert, and fully immerse yourself.

Experts, not guides

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