Day trip

Chianti and Castles Tour From San Gimignano

4.1 / 5

13 reviews

Activity provider: My Tour in Italy

Chianti and Castles Tour From San Gimignano

Activity provider: My Tour in Italy

From US$ 91.17 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
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Covid-19 precautions
Special health and safety measures are in place. Check your activity voucher once you book for full details.
Duration 6 hours
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Live tour guide
English, Italian, Spanish


  • Discover 2 estates and tour the cellars, one of which is exclusive to this tour
  • Explore traditional villages, abbeys, and castles with a guide
  • Visit 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

Immerse yourself in the picturesque Tuscan scenery on a sightseeing trip to the beautiful region of Chianti. Visit the Castellina in Chianti before enjoying a wine tasting at a winery in the 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. Later, move on to a winery in the middle of the Chianti Classico area, where you’ll have a wine tasting alongside an extra virgin olive oil tasting. The tour will end with a return to Siena.

  • Pickup and drop-off (within 20 kilometers of San Gimignano city center)
  • Travel by minivan with air conditioning
  • Multilingual guides
  • Visits to 2 wineries
  • 1 wine tasting
  • Snacks
  • Tips (optional)
Not suitable for
  • Wheelchair users

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Meeting point

Porta San Giovanni

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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.
  • Please note that pickup and drop-off is excluded from the price but can be required for accommodations located less than 10 km from the center of San Gimignano. It is possible to request it for an additional fee of 20 euros (available from April 1, 2023).
Customer reviews

Overall rating

4.1 /5

based on 13 reviews

Review summary

  • Guide
  • Transportation
  • Value for money
  • Safety

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Castle Stops and number of wineries both good. Wineries felt like they were selling more than educating, but maybe that’s most Tuscany wineries? Appreciated that we were picked up at hotel but had to ride to another town for the other participants, didn't really enjoy extra time on the road.

October 22, 2022

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

Product ID: 59865