Wine Tour in Chianti with visits to Siena and San Gimignano
What an incredible day! This tour was easily one of the highlights of our trip to Italy. San Gimignano was absolutely spectacular — one of those places that almost doesn’t seem real. The medieval architecture, towers, views and history were breathtaking, and we loved having time to walk around and explore.
The Chianti wine tasting at Il Colombaio was another highlight. We enjoyed a wonderful tasting and lunch with several wines paired with delicious food. The setting was beautiful, the wine was excellent, and the entire experience was relaxed and fun.
Siena was another beautiful stop, filled with history, incredible architecture and atmosphere. The combination of San Gimignano, the Chianti countryside and winery, and Siena made for a perfect Tuscany experience.
Our tour guide was knowledgeable, personable and engaging throughout the entire day, and our driver was excellent. They kept everything organized and comfortable while still making the day feel relaxed and enjoyable. Our small group was also wonderful, and we had so many laughs together.
An absolutely 5-star experience. Beautiful scenery, fascinating places, delicious food and wine, and a wonderful guide and driver. We would highly recommend this tour!
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jenniferlD9319HJ
September 30, 2026 · via Tripadvisor
Wonderful day!
We had an amazing Tuscan wine tour through Chianti, San Gimignano, and Siena! Franchesca was incredibly knowledgeable, engaging, and shared so much about the history, culture, and wine of Tuscany. She made an already beautiful experience even more memorable. Thank you, Franchesca, for an unforgettable day!
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D2199AMjamesh
September 30, 2026 · via Tripadvisor
A Magical Day in Tuscany
Francesca was wonderful! A great tour of the Tuscan countryside and cities with a very knowledgeable guide. The lunch was also delicious :)
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MaryEsther_M
September 29, 2026 · via Viator
Happy food happy day
Enjoy the well organized experience. Food was outstanding. Very fresh and the wine was excellent. Well worth the money.
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JaneMaine123
September 29, 2026 · via Tripadvisor
A Great Day
It was a really enjoyable day. The lunch and wine tasting were even better than expected and we really enjoyed walking the streets of San Gimignano after lunch. The other couples on the trip were fun to spend time with as well.
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erika_h
September 27, 2026 · via Viator
Exquisite
What a wonderful way to explore the outer parts of Tuscany. Chiara, our guide was a natural. Very knowledgeable in her history of Florence and of wine country. The food and wine at Poggio Amorelli was fantastic. The medieval villages of San Gimignano and Siena were amazing. Overall experience 10/10. Highly recommend.
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Bailey_L
September 26, 2026 · via Viator
Amazing! Must book.
It was fantastic! Chiara was knowledgeable, funny, and a fantastic guide around the different cities. I’d been to San gimignano and Siena before and this tour was better by far. The food at lunch was fabulous too. Chiara also had amazing recommendations for restaurants based on what we were still looking for. Highly recommend!
7
772lorid
September 26, 2026 · via Tripadvisor
Wonderful!
This was a wonderful way to see Tuscany and our guide, Mara was fabulous! The hilight of the day was our lunch at a small family owned winery. The only bummer was, we were in the van without the guide and while we had headsets so she could talk to us, many times our vans were too far apart and we lost communication.
5
533AnnaM533
September 25, 2026 · via Tripadvisor
Great pace and well organized.
This was a well paced full day tour. The meet up was easy in central tourist area and we went in vans that held at most 8 travelers plus driver. We had 7 in our van plus driver so it was not too crowded. You first stop for pictures at piazza Michelangelo and it is lovely in the morning with no tourists there. Then to Sangimignano for about an hour to n your own - it’s enough time to get a gelato, take pics of the views and do a little shopping. Then short drive to lunch with tastings of 4 wines and some olive oils and balsamic and good pasta. Then drive to Siena and about 90 min there on your own. If you want to see the church go first thing as there is a line. Then drive back to start. Our guide, Francesco, was great. He is local to Florence but had great knowledge of history, food and wine and was very fun.
It was quick visits to the 2 cities, but a good experience and you don’t have to do the driving.
7
789delinar
September 16, 2026 · via Tripadvisor
Tuscany day trip
Great trip & experience. Enough time at each city to explore and winery was nice.
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