Guided tour

Chianti and Castles Tour From San Gimignano

4.2 / 5

9 reviews

Activity provider: My Tour in Italy

Chianti and Castles Tour From San Gimignano

Activity provider: My Tour in Italy

From US$ 89.73 per person

Explore the wine region of Chianti on a half-day scenic tour from San Gimignano. Enjoy the Tuscan landscape of gently rolling hills and vineyards and taste local wines and 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
Reserve now & pay later
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Duration 5 hours
Check availability to see starting times.
Live tour guide
English, Italian, Spanish
Pickup included
Pickup and drop-off are included for accommodations located within approximately 12 miles (20 km) from the center of San Gimignano.


  • Discover 2 famous estates and tour the wine cellars
  • Explore traditional villages, abbeys, and castles with a guide
  • Visit Brolio Castle gardens and the Castellina in Chianti Area
  • Savor the flavors of local wines and typical Tuscan foods
  • Take in the scenery as you travel through Chianti's rolling hills
Full description

Experience the region of Chianti and immerse yourself in picturesque Tuscan scenery on this guided, multi-stop trip from San Gimignano. Visit ancient churches, medieval castles, and small villages where the rhythms of traditional life remain unaltered. Stop at 2 wineries for tours and tastings.

Explore the home of one of the most famous wines in the world, with its beautiful ruby-red color and characteristic violet-scented bouquet: Chianti. This wine results from a blend of Sangiovese, Canaiolo, Merlot, and Cabernet Sauvignon grapes. Get picked up directly from your accommodation in San Gimignano, then set out to discover the breathtaking landscapes that have cradled the Chianti vineyards for centuries, presenting you with a harmony of colors that can only be found in this region.

After some sightseeing, 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 you'll take part in a guided tour of the castle gardens.

When the tour of the garden ends, enjoy a tasting of two different wines. During this tour, you'll see the characteristic Castle of Brolio from the outside as well as the inner garden of the castle.

Later, move on to another winery in the middle of the Chianti Classico area, where you'll savor a second wine tasting paired with extra virgin olive oil. The tour ends with drop-off back in San Gimignano.

  • Pickup and drop-off (within 20 km of San Gimignano city center)
  • Travel by minivan with air conditioning
  • Multilingual guides
  • Visits to 2 wineries
  • Brolio Castle's gardens entry ticket
  • Wine tasting
  • Snacks
  • 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
  • Please note that from November 16 to March 14, it will require a minimum of 4 participants to be activated.
Customer reviews

Overall rating

4.2 /5

based on 9 reviews

Review summary

  • Guide
  • Transportation
  • Value for money
  • Safety

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nice afternoon

Really enjoyed this afternoon tour. We were picked up at our B&B promptly. We visited the old town of Monteriggioni where we had a half an hour to explore. Two wineries were visited next. A tour of the cellar was included at each, along with tasting of wines, olive oils and balsamic vinegar. There were 6 people on our tour, but we met up with other tour groups for the tasting at the wineries. Our driver spoke great English ! Highly recommend.

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October 20, 2019

Excellent tour to discover Chianti wines

We were very happy with this tour! The driver, very kind and prepared, took us to Monteriggioni, then we continued to the first winery, in Lornano, where we were shown the fermentation and aging cellars of the wine before starting the tasting of the wines they produce. Second stop at Poggio Amorelli, another small winery with a splendid view of the hills. Here, too, we were welcomed by a very well-trained winemaker, we tasted wine, oil, balsamic vinegar, cold cuts and local cheeses. We were very happy with this alternative tour in the Sienese countryside!

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July 13, 2016

Great tour and great guide. The interactions among the other tourists made it very enjoyable. Great presentations at the wineries; very cordial yet professionally presented.

September 17, 2019

Product ID: 59865