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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.


Customer Reviews

Lorenzina F

5 star rating: Highly Recommended January 2017

Don't miss this tour! The very best wine tasting toor! The wine was out of this world!


5 star rating: Highly Recommended January 2017

Amazing! Can and #39;t say enough positive things about this tour and our guide, Vincente! Loved hearing about his experience as a farmer to explain vineyards and wine - the most knowledgeable and professional guide we and #39;ve ever had on ANY tour! Day was perfectly paced with plenty of time to explore.


5 star rating: Highly Recommended December 2016

Great tour! Amazing wine and food. The places we visited were beautiful and we had a great time!

Andrei P

5 star rating: Highly Recommended October 2016

It was a half day trip (that and #39;s all the time we had) and we absolutely loved it. Lavinia was our guide and she was knowledgeable and very friendly. We visited Castellina Di Chianti and San Gimignano and then finished with a wine tasting session that vastly exceeded our expectations.

Renee F

5 star rating: Highly Recommended October 2016

Really had a great time on this trip. Got to see a lot of the beautiful Tuscan countryside. Great bargain.

Diane S

5 star rating: Highly Recommended September 2016

Loved it! Had a great time.our guide was very nice. Enjoyed all our stops. Would do it again!

David R

5 star rating: Highly Recommended August 2016

Fantastic wine tasting with a great host, San GIamiano was well worth a visit and would have spent more time there rather than going to the first stop at the castle which was a disappointing tourist trap. The wine tasting was very relaxed andnot rushed think we stayed near an hour later than planned.

Gregory E

5 star rating: Highly Recommended August 2016

Our tour guide Marco was amazing! He picked us up right from our hotel in Siena, on time and in black Mercedes. He not only allows us to explore San Gimignano for some time, he also took us for a quick stop at the Sienese medieval fortress of Monteriggioni. The tasting at Torciano's was fantastic as we were the only couple in the main dining area large tours sit outside in the courtyard or in their larger tasting/cask building and had a single worker spend an entire hour with us talking about the wines, the foods and just chatting. I would very much recommend this tour, especially for the price!

Luka O

5 star rating: Highly Recommended July 2016

The tour was really relaxing and fun. I can and #39;t remember the name of our guide but she was very nice and informative. It was very organized, minus the slight delay of the guide and the bus arriving due to traffic and so we had trouble finding the exact place to wait since there was no guide to meet us.


5 star rating: Highly Recommended July 2016

This was an absolutely amazing tour. There were only 5 people so we rode in a nice comfortable van. Our guide Stephan was very nice and knowledgeable. We started with a stop for cheese tasting then on to San Gimignano. We had plenty of time to see the town and have some gelato. Then on to wine tasting in Chianti where Milla took good care of us. We tried several wines paired with a great spread of food. We had a blast!

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