Small-Group Siena and San Gimignano with Dinner in a Boutique Winery

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based on 106 reviews
  • Duration:8 hours 30 minutes (approx.)
  • Location: Florence, Tuscany
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CHILD (Age : 0 to 12)
ADULT (Age : 13 to 99)


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Upto 24 hours in Advance.
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Embark on a captivating journey through Siena, San Gimignano, and Chianti's countryside. Conclude with a mesmerizing sunset and dinner. Once, Siena rivaled Florence in power and allure. Begin from Florence in a comfy minivan with an English-speaking driver, journeying to Siena.

Discover Siena through a guided walking tour, exploring Piazza del Campo where the famed Palio horse race takes place. Learn about the Contrade, medieval city districts competing in Palio. Enjoy a surprise tasting in Siena.

Next, reach San Gimignano, renowned for medieval skyscrapers and preserved tower houses, crafting a unique skyline. After leisure in San Gimignano, witness a breathtaking sunset. Relish wine tasting and a traditional Tuscan dinner in Chianti. Explore ancient cellars, gaining insight into wine production.

A remarkable experience, embracing Tuscan gems, gastronomy, and wines.

Numbers are limited to 16 on this small-group tour, ensuring a personalized experience.


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Posted By : NEIL_U
Amazing tour. 3 places. We were in the town of Siena during the Palio or the famous horse race. San gimignano was just beautiful. This was free time to explore. Hit gelateria dondoli - must do. Tried the native VERNACCIA wine. Then had winery tour and an amazing dinner with really nice people that were on our tour of frattagio del bargnola.
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Posted On : 2024-06-30 03:28:04 full ratings


Posted By : 782melindaw
The tour was amazing. Our guide was very informative and friendly. The vehicle was very comfortable. We saw some amazing sites, took lots of photos and lunch was delicious
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Posted On : 2024-06-18 01:54:05 full ratings


Posted By : gregmG269IK
The overall trip was good. Siene was beautiful, our guide was informative but she seemed a little rushed and a little hard to understand at times. Be ready for some serious climbing. Lots of up and down steep hills. We got 40 mins in San Gimignano which was time enough to find a bathroom. Nothing was told about the town so not sure why we stopped there. On to the best part being the Winery. The farm was beautiful, interesting tour of the garden and wine cellars and ending the evening was a wonderful tasting and dinner. Not a red wine person but our traveling companions loved the wine. Their EVO was also wonderful. Bruschetta, Pesto, Pasta, Hunters Chicken and a delicious strawberry cake all wonderfully prepared. The worst part was the Tour Leader who said basically nothing about anything on our 2 hours of driving. Little information about the towns, countryside anything. Her and the driver were nice but no engagement. The last item was the driver flew almost the entire trip, I’m sure we never came close to the actual speed limit in the winding rough roads.
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Posted On : 2024-05-05 02:00:25 full ratings


Posted By : kyreview4u
Sights were beautiful but ours were very rushed, only 50 minutes in San Gimignano and guide did not accompany the rest of the tour group into town because she was getting a group of elderly individuals settled in a cafe because the walk was too strenuous for them. Likewise, had only a little over an hour in Sienna and the guide kept walking ahead of everybody oblivious to the old folks who could not keep up. Arrived for "sunset" dinner at winery well after dark. Food was good and enjoyed wine and olive oil tasting. Transport bus was like an oven with passengers standing up to put their faces near the overhead vents, although the driver and guide enjoyed the air conditioning blowing directly on them. Tour has great potential if better organized.
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Posted On : 2023-10-09 12:39:46 full ratings


Posted By : Krista_H
Thoroughly enjoyed this day trip from Florence, with an opportunity to see the Tuscan countryside and the lovely towns of Siena and San Gimignano. The time in each town is somewhat limited but you get a chance to walk and explore a bit on your own. The winery visit and dinner at Fattoria Di Banola was a big highlight of our entire trip to Italy. I only wish there had been more time here. As it was nearly dark when we arrived, we had only a short time to see the surrounding countryside and vineyards. The sommelier Irena welcomed us with a tour and explanation of the wines we tasted. We were also greeted by the marchesa, Giovanna, who was a hoot!
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Posted On : 2023-09-17 11:48:24 full ratings


Posted By : 365marh
Everything was great! The guide and bus driver were awesome. Thank you! I had a great time and enjoyed the pasta
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Posted On : 2023-07-12 12:35:50 full ratings


Posted By : U3266TRdd
The views were amazing. The Florencetown tour guide was lovely. The Siena tour was a let down and not very engaging. Siena is more than what we experienced during this tour. The winery was small and underwhelming. The wine was fantastic however, the food was meh. Overall, I wouldn't recommend the tour it isn't worth the price. I would rent a car and take the day to explore Siena and the surrounding areas at your own pace.
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Posted On : 2023-07-05 06:49:03 full ratings


Posted By : Sandra_G
I think the winery tour and explanation were fantastic, but the Siena tour felt a bit average, the guide was difficult to understand and wasn't very engaging. Unfortunately I wasn't a big fan of some of the wines and the one wine I liked was told that they dont ship to Australia- I think that should be mentioned on the tour details.
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Posted On : 2023-07-04 12:29:18 full ratings


Posted By : Shari_F
This tour was great, the guide was interesting to listen to as she gave us little details about the towns we went to. She was friendly and helpful. The winery was interesting and quite beautiful. The wine was great and the dinner was delicious.
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Posted On : 2023-07-02 16:43:54 full ratings


Posted By : ZSchatz
Driver and guide were both knowledgeable and friendly. The walking tour of Siena was quick, but offered a great overview of the history of the city, the cathedral, and the annual horse race. The highlight of the day trip was dinner at the winery. The winery was a boutique, family owned property with wonderful wine. We were treated to a surprise opera performance before dinner with the winery owner and her family and friends. It was an intimate and fun experience with great food and wine. Would definitely recommend.
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Posted On : 2023-06-26 21:38:07 full ratings