Guided tour

From Siena: Chianti and Castles Tour with Wine Tastings

4.4 / 5

78 reviews

Activity provider: My Tour in Italy

From Siena: Chianti and Castles Tour with Wine Tastings

Activity provider: My Tour in Italy
Likely to sell out
Likely to sell out

From US$ 89.71 per person

Explore the scenic wine region of Chianti on a half-day tour from Siena. Enjoy a Tuscan landscape of gently rolling hills and vineyards and taste Chianti wines paired with Tuscan products.

About this activity

Free cancellation
Cancel up to 24 hours in advance to receive a full refund
Covid-19 precautions
Special health and safety measures apply. Learn more
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Duration 5 hours
Check availability to see starting times.
Live tour guide
English, Spanish, Italian
Pickup included
Please be ready at your pickup location 15 minutes before the scheduled pickup time.


  • Discover the breathtaking landscapes of Chianti via minivan
  • Explore ancient churches, medieval castles, and small villages
  • Enjoy wine tastings at 2 renowned wineries in the Chianti area
  • Savor bruschetta paired with typical Tuscan cold cuts and cheese
  • Visit the Brolio Castle's Gardens and the Castellina in Chianti
Full description

Immerse yourself in the picturesque Tuscan scenery on a sightseeing trip to the beautiful region of Chianti. Explore the gardens of the Brolio Castle and visit the Castellina in Chianti before enjoying wine and local product tastings at 2 wineries in the Chianti area.

The beautiful ruby-red color and the characteristic bouquet with scents of violet are the special features that reveal the identity of one of the most famous wines in the world: Chianti. This wine results from the wise blend of Sangiovese, Canaiolo, Merlot and Cabernet Sauvignon grapes.

On this trip, discover the breathtaking, uncontaminated landscapes that have been cradling the Chianti vineyards for centuries, presenting you with a harmony of colors that can only be found in the hills of this region.

The sounds, scents, and flavors of this land will capture your senses through a unique experience. Visit ancient churches, medieval castles, and small villages where the rhythm of life remains unaltered over time.

The tour continues with a visit to a charming wine estate. Here, you'll have the chance to see the area close to the famous Castle of Brolio and join a guided walk of the castle gardens. When the tour of the garden ends, join a wine tasting paired with typical Tuscan food.

Later, move on to another winery in the middle of the Chianti Classico area, where you’ll have a second wine tasting alongside an extra virgin olive oil tasting. The tour will end with a return to Siena.

  • Pickup and drop-off shuttle service
  • Transportation via minivan
  • Bilingual guide
  • Multi-stop tour
  • Wine tasting at 2 Chianti wineries
  • Extra virgin olive oil tasting
  • Tasting of typical Tuscan food
  • Tips (optional)
Not suitable for
  • Wheelchair users
Covid-19 precautions
Safety measures in place
  • All areas that customers touch are frequently cleaned
  • You must keep social distance while in vehicles
  • The number of visitors is limited to reduce crowds
Traveler requirements
  • You are required to bring and wear a mask

Select participants and date



Important information

Know before you go

  • Customers must be able to climb and descend stairs.
  • This is a small-group tour with a maximum of 8 people in the minivan.
  • Participants are required to provide a complete vaccination certificate, proof of COVID-19 recovery within 6 months, or a negative COVID-19 test taken within 48 hours of the tour. One of these documents is mandatory to join the activity; otherwise, no refund will be provided.
Customer reviews

Overall rating

4.4 /5

based on 78 reviews

Review summary

  • Guide
  • Transportation
  • Value for money
  • Safety

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Experience was good , possibly the 1st stop for wine tasting may have been more interesting if we had have been told about the types of wine more it was a bit light on info . The drivers were great and the stops at the castle and village also the last stop was really good and I bought some wine also

June 22, 2022

This tour was a lot of backroads driving and not much time at the castles. You don’t actually tour the castles, you can walk around them. The view was amazing and the countryside, though a few of us were car sick from the high speed country roads between towns. The guide is really just a driver. He seems to know the area well, but didn’t offer a lot of information as we drove.

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April 10, 2022

Our driver was both very knowledgeable and fun. We visited two beautiful wineries and one medieval village. I wouldn't really call it a "castle tour" because we did not tour any castles. But it was a thoroughly enjoyable day in spectacular countryside. The rolling hills, the beautiful Tuscan weather (we went in February -- no crowds, beautiful bright blue skies, perfect) and one winery in particular that has been operated by one family for many generations. The settings were gorgeous.

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February 24, 2020

Product ID: 8413