Chianti & Castle: Small-group Afternoon Wine Tour from Siena

Siena Ville
5 Hours
Min 1, Max 20
English, Español, Italiano
Cancel Free: 2 Days Prior

Here is what's in store for you

Embark on a half-day scenic journey from Siena to explore the stunning Chianti wine region, renowned for its rolling hills, lush vineyards, and iconic cypress trees. Savor exceptional Chianti wines and authentic Tuscan delicacies as you immerse yourself in the natural beauty of this renowned landscape.

Your adventure begins with a visit to the charming town of Castellina in Chianti, followed by a wine tasting at a local vineyard. Here, you’ll discover the essence of Chianti—a wine with a distinct ruby-red hue and a bouquet of violet aromas. This world-famous wine is crafted from a blend of Sangiovese, Canaiolo, Merlot, and Cabernet Sauvignon grapes. As you journey through the breathtaking countryside, you’ll be captivated by the unspoiled landscapes that have nurtured the Chianti vineyards for centuries, offering a vibrant display of colors unique to this region. Along the way, you’ll have the chance to explore ancient churches, medieval castles, and quaint villages that have preserved their timeless charm. One of the highlights of the tour is strolling down the iconic cypress-lined avenues that have become synonymous with Tuscan postcards, offering perfect photo opportunities.

Your day continues with a visit to a renowned winery in the heart of Chianti Classico, where you'll enjoy a tasting of both wines and extra virgin olive oil. The serene atmosphere and panoramic views create an unforgettable experience, making it the perfect way to truly appreciate the flavors and beauty of Tuscany. The tour concludes with a return to Siena, leaving you with lasting memories of one of Italy’s most treasured regions.

Why choose Winedering?

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Free Cancellation

Free cancellation until 2 days before the start.

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Over 10200 verified reviews from our community.

What's Included

  • Travel by air-conditioned minivan for up to 8 people
  • Expert multilingual guide
  • Tour of two famous estates with winery visit (one exclusive)
  • Tasting of 2-3 wines at each winery
  • Olive oil tasting
  • Visit to Castellina in Chianti

What's not included

  • Personal expenses

Where we are and how to reach us

Meeting Point: Siena: Stazione di Siena

Get directions

Booking details and conditions

You can cancel for free until 2 Days Prior

This is a small group tour with a maximum of 8 people in a minivan or 20 people in a minibus.
Participants must be able to climb and descend stairs.
A vegetarian menu is available upon request.

Frequently Asked Questions

You can easily check all the prices clicking on 'Book or Gift' button, selecting a date and choosing your options
Unfortunately, pets are not allowed for this experience.
You can do it in less than a minute! Click on the 'Book or Gift' button, choose the date and time among those available and fill in the rest of the requested information.
Click on the 'Book or Gift' button! You'll find an interactive calendar with dates and times!
The languages available for this amazing experience are: English, Español, Italiano. You can choose one of these languages during the booking process.
You can cancel for free until 2 Days Prior

User Reviews (1)

Jeroen
New on Winedering
· April 9, 2026
Chianti & Castle: Small-group Afternoon Wine Tour from Siena
We had a very nice experience, well organized. The bus was nice, the stops were very interesting, there were some beautiful sites and views. The tastings were fun and the Chianti wines, olive oil, snacks, and sweet aged vinegar were very tasteful. Valeska was a great tour guide, fun, positive, and helpful!
None
Reply from MY TOUR - MY RENT
Dear Customer,
Thank you for your feedback!
We’re delighted you enjoyed the tour, the tastings, and the beautiful stops. Valeska will be thrilled to hear your kind words!
We hope to welcome you on another tour soon.
Best regards,
my Tour in Italy

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