• Location: Siena, Italy
  • Duration: 5 hours (approx.)
From USD $ 49.83 View price calendar

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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

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

Rachel V

5 star rating: Highly Recommended March 2018

This tour was great. Our driver was very knowledgeable about the area and gave us information only a local would know. We had time to see a typical town in the Chianti region and then spent some time in San Gimignano. It would have been nice to have had more time there but after we went to a wine tasting where we had the chance to try about 7 different wines with light appetizers. I would definitely recommend this tour.

Ana D

5 star rating: Highly Recommended March 2018

The driver and guide Paolo was nice friendly and gave us plenty of usefull information : best of friendly italian charm :

Daniel M

5 star rating: Highly Recommended October 2017

The tour was absolutely the best from start to finish. Our guide was so nice and so engaging that the ride itself was enjoyable. The wine tasting was absolutely the best, the young lady that gave us the tour and tasting couldn't have been any better. She was funny, charming and insightful. Great time

Peter S

5 star rating: Highly Recommended October 2017

Very nice tour of San Gimignano and visited a family winery where we got to taste some wonderful olive oil and good wine. Nice way to see the countryside, especially for a first time visitor.

Calvin D

5 star rating: Highly Recommended September 2017

A real bargain and very entertaining. This trip takes you into the beautiful tuscan countryside and quaint towns with long histories. The wine tasting was the best ever in Italy. Would highly recommend!

Jeremy F

5 star rating: Highly Recommended September 2017

Wonderful tour, wonderful guide and great value. The only thing I would note is that this tour was advertised as 5 hours but was actually 6 hours - important to know if you are making dinner reservations.


5 star rating: Highly Recommended July 2017

This was an awesome tour. The winery was amazing Julia was a gracious host and made it such fun to learn about the different types of wine that her winery makes, our tour guide was fantastic Leviana was very knowledgeable of the region and had language skills that allowed her to speak with everyone on our tour, the countryside is beautiful there is a significant portion of riding, but the ride is comfortable and you can really see the fact that this an agriculture based economy given the number of farms and fields, and you really could not ask for a better day trip. Stopping in Castelina and San Gigminano were both great places to get a chance to explore and was such a nice reprieve, since these are smaller cities of Tuscany. I am so glad we did this. Such an amazing trip!

Linda D

5 star rating: Highly Recommended July 2017

Excellent tour. San Gimignano was very crowded but enjoyable. The highlight of the tour was the Chianti Wine Tasting. It was educational and entertaining and the food plate was delicious as was the wine. I would definitely recommend this tour.

Karen K

5 star rating: Highly Recommended July 2017

An excellent trip and well worth the money . Loads to see and do on this terrific trip. First stop was in an enchanting little place called monteriggioni where we stopped for a glass of wine and a piece of delicious sienna cake otherwise known as panforte. Then back on the mini bus to our next destination of Castellona in Chianti where we had a little pit stop to see the church and wandered around the lovely wee streets.and a pretty stunning view of the rolling Tuscan hills.then off to San Gimignano which is another absolutely stunning mediaeval walled city where I had been in 1978 a total blast from the past and the most wonderful thing was it hasn't changed one bit in 39 years how incredible is that? Walked through the wonderful streets to the centre and found the well . Famous for having an secret underground pool , I only found that out recently. After a spot of lunch it was back onto the bus for our last but not least stop of the day a wonderful vineyard where we were entertained by the most incredibly handsome and charming vintner who looked like a better version of David Boreanaz.... who played Angel in Buffy the vampire slayer. Utterly delicious and so were the wines oils and biscotti we had . No hard sales pitch at all just a wonderful relaxing experience in a beautiful part of Tuscany... great tour guide too . Very good looking and utterly charming and knowledgeable. This trip is a most definitive must do/see.


5 star rating: Highly Recommended July 2017

This tour was amazing!

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