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Soak up the local vino and small-town charm of San Gimignano with this 5-hour wine tasting trip from Siena. Explore San Gimignano first at your leisure, spotting landmarks such as the Collegiata and Pizza del Duomo while strolling the medieval streets. Afterward, travel deeper into the Tuscan hills, where you’ll enjoy an intimate winery tour. Sip and swirl Chianti blends with an inside look at the wine-making process. Your trip will conclude back in Siena.


  • Half-day San Gimignano 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
  • 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 hop aboard your coach toward San Gimignano. Learn about the UNESCO-listed town from your guide as you go, a destination complete with impressive towers, old city walls and set on a hill overlooking the Val d’Elsa valley.

After arriving, explore the medieval town at your own speed. Stroll along the ancient pilgrimage trail of Via Francigena, check out the architecture in Piazza del Duomo or browse the artisan pottery and crafts in the local shops.

Then reunite with your guide and journey to the Chianti region, celebrated for its world-class wine and stunning landscape. Take a winery tour, exploring the vineyards, bottling rooms and cellars of a Tuscan estate.

After learning about the production process, treat your palette to an array of reds and whites, noting the distinct characteristics of each. A selection of traditional Tuscan snacks, such as local cheeses, bruschetta or cured meats, will complement your tastings.

After five hours of sightseeing and fine wine, your tour will conclude with transportation back to Siena.


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

Customer Reviews


5 star rating: Highly Recommended July 2016

Great wine, and visited two fantastic towns!

Philip J

5 star rating: Highly Recommended June 2016

Great guide. Visited one retail outlet for a winery bought one bottle!, then had time to walk the main street in San Gimignano spelling?, then a wonderful light lunch and wine tastings in a beautiful Tuscan winery. We bought over 200 Euros of product. Guess that says it all. Highly recommended!

Alison A

5 star rating: Highly Recommended April 2016

Excellent way to spend an afternoon touring the beautiful Tuscan scenery and experiencing some fabulous wine!

Mary Rose L Canada

5 star rating: Highly Recommended March 2016

The tour was excellent with lots of free time to explore on our own. The wine tasting was great and very informative with no pressure to buy any wine. Our guide Giovanni was very good he spend time explaining the history and area information and gave us background information on the Italian family traditions and way of life. I would highly recommend this tour from Siena.

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

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