Guided tour

From Siena: Chianti and Castles Tour with Wine Tastings

4.5 / 5

84 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

From US$ 87.54 per person

Likely to sell out

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
Reserve now & pay later
Keep your travel plans flexible—book your spot and pay nothing today.
Covid-19 precautions
Special health and safety measures apply. Learn more
Duration 5 hours
Check availability to see starting times.
Live tour guide
English, Italian, Spanish


  • Discover the breathtaking landscapes of Chianti via minivan
  • Explore ancient churches, medieval castles, and small villages
  • Visit 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 picturesque Tuscan scenery on a sightseeing day trip from Siena to the region of Chianti. Explore the gardens of the Brolio Castle and visit the Castellina in Chianti before partaking in a wine tasting experience at a wine estate.  

Board a spacious and climate controlled van in a centrally-located meeting point in Siena. Admire the Italian countryside on the ride as you pass thorugh pristine landscapes that have been cradling the Chianti vineyards for centuries.

Discover a harmony of colors that can only be found in the hills of this region. Delight your senses as you dive into the sounds, scents, and flavors of this land will capture your senses through this unique experience. 

Visit ancient churches, medieval castles, and small villages where the rhythm of life remains unaltered over time. Continues to a charming wine estate. Hve the chance to see the area close to the famous Castle of Brolio and join a guided walk of the castle gardens. 

Indulge in a wine tasting paired with typical Tuscan food. View the beautiful ruby-red color and the characteristic bouquet with scents of violet are the special to Chianti wine. Savor this blend of Sangiovese, Canaiolo, Merlot and Cabernet Sauvignon grapes.

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

  • Transportation via minivan
  • Bilingual guide
  • Multistop tour
  • Visit at 2 Chianti wineries
  • Extra virgin olive oil tasting
  • 1 wine tasting
  • Tips (optional)
  • The second wine tasting
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



Meeting point

Meet in front of the bar La Lizza.

Open in Google Maps ⟶
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

4.5 /5

based on 84 reviews

Review summary

  • Guide
  • Transportation
  • Value for money
  • Safety

Sort by:

Traveler type:

Star rating:

The tour was very nice, our tour guide was on time and explained some nice facts about the Chianti region and wines on the way. We visited beautiful privately owned Castello di Brolio and winery and then a winery in Lornano. It's a nice tour and we recommend it because it not long and starts in the afternoon at 2pm.

July 12, 2022

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.

Read more

April 10, 2022

Product ID: 8413