4.5 star rating: Recommended 49 Reviews

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  • Location:Siena, Italy
  • Duration:5 hours (approx.)

Chianti Wine Tasting and San Gimignano Day Trip from Siena

Spend an afternoon in Tuscany, visiting the small towns of San Gimignano and Castellina in Chianti, on a half-day tour from Siena. Hear the history of the region from an expert guide, and then enjoy some free time to explore the medieval hill town of San Gimignano, discovering sites like Piazza del Duomo and Via Francigena. Then, travel to the heart of the Tuscan hills for a tour of a winery in Castellina in Chianti, where you'll learn about Tuscan wine, and enjoy a wine-tasting session, too!


  • Half-day San Gimignano and Castellina in Chianti tour from Siena
  • Hear tales of San Gimignano’s medieval history from an expert guide
  • Explore the hilltop town at your own pace, seeing sights like Via Francigena and the Collegiata
  • Visit the charming village of Castellina in Chianti and take a tour of a Tuscan winery
  • Learn about wine production in Chianti and discover the difference between Super Tuscan and Gallo Nero wines
  • Sample red and white Tuscan wine during a tasting session, and enjoy a plate of antipasto

Recent Photos of This Tour

What You Can Expect

Chianti Wine Tasting and San Gimignano Day Trip from Siena

Enjoy the views from beautiful San Gimignano!

Meet your guide in central Siena and travel north through the Tuscan countryside by air-conditioned coach. Your destination is San Gimignano, a lovely medieval town complete with old city walls and impressive towers. Perched on a hill overlooking the lush Val d’Elsa valley, the UNESCO-listed town is popular for its views, history and architecture.

Learn all about the town from your guide as you travel, and then enjoy roughly 1.5 hours of free time in San Gimignano to explore at your own pace. Admire the stunning architecture around Piazza della Cisterna and Piazza del Duomo, and have your camera ready for photos by the Collegiata – San Gimignano’s Romanesque cathedral. Perhaps take a stroll along the Via Francigena strip – an ancient pilgrimage road – or visit the shops to browse the locally made handicrafts and beautiful Santa Fina pottery.

Meet your guide at the pre-arranged time and travel deep into the heart of Tuscany, to the famous Chianti region. Gaze out at the emerald green hills, laden with grape vines and olive groves, and stop in the postcard-perfect village of Castellina in Chianti. Visit a renowned winery here for a tour, exploring the cellars, vineyards and bottling rooms of an impressive Tuscan wine estate.

Hear about wine production in the Chianti area – the grapes used, the terrain and the climate – and learn about the different classifications of Tuscan wines, such as Super Tuscans and the prestigious Gallo Nero label. After your tour of the estate, sit down to sample a selection of the best!

Sip on different reds and whites, noting the characteristics that set them apart from other Italian wines. While sampling and discussing the wines, tuck into a selection of typical Tuscan snacks. The dishes vary according to what’s available on the day of your tour, but you can expect delights like garlicky bruschetta, mild cheeses and Tuscan salami or ham; you won’t be disappointed!

After relaxing at the winery, return to your coach for the journey back to Siena. Finish your tour in the early evening back at the start point.

Please note: occasionally this tour may run in reverse order, meaning your visit to Chianti will take place before San Gimignano.

Customer Reviews

Nikkitha B

5 star rating: Highly Recommended November 2015

Knowledgable guide, beautiful surroundings, great food, completely magical.

Crystal B

5 star rating: Highly Recommended October 2015

WOW! great Chianti, Brunello and Super Tuscan wine! Had fun time at San Gimignano, very friendly and the country side was lovely

Simon W

5 star rating: Highly Recommended October 2015

Wonderful trip. Margherita, our guide, was very informative.


5 star rating: Highly Recommended October 2015

This was an amazing trip and if I visited Tuscany again I would probably do it again. Our guide was lovely and our bus mega comfortable and the route perfectly planned. The highlight was the final wine tasting whic I had not expected to take long but was amazing. The location superb the wine delicious along with the other offerings and delivered in a very entertaining manner. We laughed so much but also learnt so ugh and tasted some of the best wine ever. If you have any doubts about this trip so long as you can cope with walking uphill at each venue you will have a day to remember.


5 star rating: Highly Recommended September 2015

It was a very successful experience. Congratulations organization. Tuscany is wonderful

Gail P

5 star rating: Highly Recommended August 2015

What a fun trip. Our guide, Daniel, was very knowledgeable and San Gimignano is beautiful. We had 1.5 hrs there, which was enough for us it was raining a little and then we went on to the wine tasting, which was so much fun. Yes we got tipsy, but hey we weren't driving. The beauty of taking a tour

Sreenath H

5 star rating: Highly Recommended July 2015

Oh, the visit to the winery was awesome. Wine tasting was a lot of fun. Going to San Gimignano was like visiting a place out of this world. The walled village, colourful shops, its tall towers with its unending flights of stairs, its famous gelatos......... you wouldn't want the trip to end. A must trip for everyone visiting Siena.


5 star rating: Highly Recommended June 2015

This tour was amazing!


5 star rating: Highly Recommended June 2015

Fantastic tour, excellent value for money. Loved the wine tasting we were given informative talk on the different wines and got to sample them all, along with being provided delicious finger food. Beautiful winery. Also loved San Gimignano, excellently preserved village, probably best we visited.

armando d

5 star rating: Highly Recommended June 2015

Great time lovely people and Torrciano winery great experience.

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Tour code: 5919CHIANTISANGIM


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