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San Gimignano, Siena, Monteriggioni, Chianti and Lunch with Wine Tasting

5 Reviews

Shared Tours
From € 67.00
Select Dates and Travelers


  • Visit two stunning UNESCO World Heritage Sites and go back to the Middle Ages
  • Discover Siena Top Sights with a local Professional Guide
  • Wonderful views of Tuscan rolling hills and visit of two medieval Villages in the Chianti countryside
  • Enjoy the Visit to the cellars and vineyards together with a typical Lunch in a cozy Chianti Winery
  • Taste 3 different Chianti Wines, Balsamic vinegar and "vin santo"
From: € 67.00
Duration: 11 hours Approx.
Start Time: 08.00 am
Season: All year round
Meeting Point / Terminal: Piazzale Montelungo, Florence - at the end of the ramp connecting with the train station View meeting point with Google Maps - Piazzale Montelungo

Your memorable journey starts with the charming San Gimignano, world famous walled town located on a hilltop, which remained intact through the centuries, renowned for its tall towers, wonderful frescoes and many other valuable works of art: here the tour leader will lead you to the historical center, where you will have around 2 hours of free time for a fascinating discovery.
A short distance from San Gimignano you will visit the charming historical hamlet of Monteriggioni (*), an amazing small medieval village enclosed by its famous walls, which remained standing to this day: free time for inside visit.
From Monteriggioni, crossing the gently Chianti rolling hills, a short ride will take you to a cozy Winery, where you can relax and enjoy the fantastic world of Chianti with its wine and typical products: tasting of three fine wines and balsamic vinegar followed by a Chianti style lunch: 3 course with “zero food miles” products which ends with "cantucci e vin santo".
Later on, getting to Siena, you will meet your professional local guide who will lead you on a comprehensive guided tour of the historic center. Strolling along the narrow medieval streets of the city, flanked by splendid palaces and historic shops, passing through Piazza del Campo, of which the Palazzo Pubblico (Town Hall) is the focal point, you will get to the spectacular Cathedral of the 12th century (inside visit if option selected), of which you can admire the magnificent architecture and the splendor of the polychrome marbles.

You will also have some free time to end your perfect day enjoying the unique atmosphere of this amazing city, before the return to Florence in the evening. 

Please note that the order of the visits may change

(*) From November to March, the itinerary does not include the stop at Monteriggioni and the return to Florence is approx 30 minutes earlier     

Lunch Sample Menu

Enjoy 3 course-lunch which includes: Appetizer with cold cuts ( prosciutto, finocchiona, salami ) bruschetta olive oil and truffle oil pecorino cheese with balsamic vinegar and green salad; Main Course with penne with meat ragout and parmesan cheese and Dessert with homemade tart with jam and vinsanto. Tasting of 3 different wines. 

  • Caf Tour’s Team Assistance at the meeting point
  • Transport by air-conditioned Coach with Wi-Fi on board 
  • Licensed Tour Escort
  • Visit to the cellars, vineyards and 3 course typical Tuscan lunch in a Chianti Winery
  • Tasting of three different Chianti Wines, balsamic vinegar plus “vin santo”
  • Sample Lunch Menu: Appetizer with cold cuts ( prosciutto, finocchiona, salami ), bruschetta olive oil and truffle oil, pecorino cheese with balsamic vinegar and green salad; Main Course with penne with meat ragout and parmesan cheese; Dessert with homemade tart with jam and vinsanto
  • If Option Selected: Guided Visit in Siena with Professional local Guide (April to October monolingual Tour)
  • If Option Selected: further Visit, led by Professional local Guide, inside Siena Cathedral and Libreria Piccolomini with skip-the-line Ticket


It is mandatory to arrive at the meeting point at the mentioned check in time. In case of delay it will not be possible to join the Tour, nor to have a refund or reschedule the tour.

4.4 5 Reviews

Brad Cooper, 01/2020
"We did the tour to San Gimignano, Siena, Monteriggioni and we really enjoyed it. We also had lunch with wine tasting in the Chianti region, which was really delicious and also interesting as the people in the winery explained a lot of interesting things. At the end we were a little tired but it is really worth it!"
Erika Hunt, 02/2020
My family and I took part in this tour and we really liked it: well organized, the guide was very friendly and told us interesting information about Tuscany in general and all the cities we visited; the driver was competent and funny too, and, finally, the tour met our expectations: we had time to visit San Gimignano, Siena and Monteriggioni on our own and the lunch with wine tasting was a relaxed and funny way to know more about this beautiful land. The landscape and the cities were amazing. Thanks CAF!
Good organisation and pleasant tour
Kimberly Grant, 11/2019
Tour was very well organised, guides were very friendly knowledgeable and taking very good care about the group with them. Duration was almost same as mentioned in the tour information and most of all the good time management of the organiser. San Gimignano is better than we are used to imagine it! Lunch was delicious and we also bought some bottles of good Chianti wine!
Loved the day!
Eric Lerman, 04/2019
Fabulous day seeing Tuscany and visiting local towns. Guide on bus was professional and informative and driver very competant. Sienna was fabulous and the guided walking tour perfect our guide brought the city to life on the tour with her knowledge of sienna and local history. The wine tasting rounded off the day perfectly. All in all the tour was well presented and well organised the time spent on the bus was minimal and the day went over too quick..well worth it and would def recomend to anyone. Loved the day !
Guía muy cautivadora!
Angelica Bombilla, 07/2019
Nos enamoramos de San Gimignano, la ciudad es preciosa! Tuvimos todo el tiempo necesario para tomar fotos y relajarnos, la organización del tour es perfecta! Nos explicaron la historia de Siena y la guía fue muy cautivadora!
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