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Spend a half-day exploring San Gimignano, one of the most bewitching medieval hill towns in all of Italy, on this guided tour from Siena. Indulge in a local wine tasting and learn about the intriguing history of the town (and why its many medieval family towers are still standing (while other towns’ were knocked down centuries ago). Take some free time to explore on your own, visiting the main sites, including the beguiling Collegiata cathedral, among many others. The number of participants on this small-group tour is limited to just eight, so you’re sure to get plenty of personalized attention from the guide.


  • Half-day San Gimignano trip and wine-tasting session from Siena
  • Learn about San Gimignano’s medieval history and architecture from a friendly guide
  • Enjoy free time in the hilltop town, seeing attractions like the Collegiata and Via Francigena
  • Take a tour of a Tuscan winery and try the region’s famous Vernaccia white wine
  • Snack on a plate of antipasto (crostini, olives, cheese and more) while sampling Tuscan wines
  • Small-group tour with a maximum of eight people ensures a more personalized experience

What You Can Expect

San Gimignano Day Trip from Siena with Wine Tasting

Enjoy a wine-tasting session in one of San Gimignano's wineries!

Go from one amazing medieval Tuscan town to another on this halfday guided tour of spectacular San Gimignano. From your centrally located hotel in Siena, hop in a minivan or coach and make the short drive to this impressive UNESCO World Heritage-listed hill town. 

On the way there, learn from your guide the history of the town and hear about the area’s unique cultivation of saffron, which has been revived in recent years. Once there, stroll the streets, taking in the medieval ambience. Visit one of the handful of towers that exist in the town. Nicknamed the ‘medieval Manhattan,’ San Gimignano boasts an impressive handful of tall matchstick-like towers, some of which can be ascended. 

Linger in ambient Piazza della Cisterna and be sure to take some time to drink in the incredible views of southern Tuscany. Pop into the impressive Romanesque cathedral, the Collegiata. And learn about the Via Francigena, a pilgrimage route, stretching from Canterbury in England to Rome, that goes right through San Gimignano. 

After some free time, meet up with your guide and head deeper into the Tuscan countryside. Take a tour of a popular winery and sample some of the well-known wine from the area, Vernaccia. It’s the only Tuscan white wine that has the classification of DOCG. Take some time to enjoy this crisp white’s floral taste profile and follow the vino with some Tuscan treats, such as locally made cheese, olives and bruschetta. 

When the tasting finishes, board the minivan for the short ride back to Siena where the tour concludes at your hotel. 

Customer Reviews

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!

Leomar M

5 star rating: Highly Recommended June 2016

Great day at San Gimignano, We loved

Tori G

5 star rating: Highly Recommended June 2016

Brilliant, wonderful guide, excellent winery a wonderful experience would do it again!!!

Alice A

5 star rating: Highly Recommended July 2015

My husband and I were delightfully surprised by how amazing this tour actually was. The tour guide was outstanding!! He was friendly and very knowledgable of the Tuscany region. The tour only included us and another couple, which was a lovely surprise. It made it more personal. This tour is a must!!

david p

5 star rating: Highly Recommended June 2015

We had a great time. The wine tasting event was spectacular. My wife and I fell in love with San Gimignano. I would definitely recommend this tour to anyone wanting to visit wine country.

michelle F

5 star rating: Highly Recommended December 2014

This tour was amazing!


5 star rating: Highly Recommended December 2014

This tour was great! Danny our guide was very knowledgeable about the Siena and San Gimignano area and made for a very enjoyable tour. The wine tasting was excellent. I would highly recommend this tour.


5 star rating: Highly Recommended October 2014

This was a fun tour. We had a couple of hours in San Gimignano which was great. It's a delightful little town that I think you could spend a couple of days enjoying. The wine tasting over lunch was absolutely hilarious. The guy running the wine tasting was a real comedian and had all the groups there laughing most of the time. The wines were very nice and the oils were great. It was just an all-round great experience.

Joan L

5 star rating: Highly Recommended October 2014

This tour was amazing!

Jessica R

5 star rating: Highly Recommended October 2014

Fantastic tour. The guide was very knowledgeable and entertaining. I would have liked to have more time in San Gimignano (we had about 45 minutes) but the wine tasting was fantastic. They do not skimp on the wine as we each received about 6 glasses. We also got to try a variety of olive oils. The truffle oil was fantastic.

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