Tuscany Day Tour: Explore Medieval Siena, San Gimignano, Monteriggioni with Chianti Wine Tasting

Embark on a full day tour of Tuscany, exploring the medieval towns of Siena, San Gimignano, and Monteriggioni. Indulge in a Chianti wine tasting and soak in the breathtaking views. A perfect day-out to relax and replenish your spirits.

Duration: 10 hours, 30 minutes
Cancellation: 24 hours
Highlights

The tour starts from Florence and leads you to the atmospheric Medieval gem of Monteriggioni. It was built in 1203 and became a strategic garrison town with its 14 towers, Dante called it the “ring-shaped citadel”. Here you can steep yourself in the past and prepare yourself for the wonders of Siena
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Here your local guide will reveal to you its main…

What's Included
  • Professional guided tour of Siena (headsets not included in semi-independent option)
  • Free time to explore San Gimignano and Monteriggioni
  • Wine tasting experience at a Chianti estate (2-3 wines)
  • Sample regional products and extra-virgin olive oil
  • Travel in comfort with a fully-equipped GT Coach, including free Wifi
  • Assistance from an expert, multilingual Tour Leader
What's Not Included
  • Gratuities
  • Hotel pickup and drop-off
  • Siena Cathedral tickets (approx. 7€ pp)
  • Lunch
Additional Information

Experience a full day exploration of the prime attractions in Central Tuscany, complete with a delightful Chianti wine tasting. Traverse through the stunning rural scenery to your first stop, the radiant city of Siena, known for its unique square and Gothic-style town hall. Next, navigate towards San Gimignano, often referred to as the Medieval New…

Location
Piazzale Montelungo
TOURS & NEWS KIOSK AT PIAZZALE MONTELUNGO BUS TERMINAL Located at 5-10 minutes walking distance from Santa Maria Novella Train Station. Look for our staff wearing a FUCHSIA CIAOFLORENCE JACKET and holding a CIAOFLORENCE CLIPBOARD!
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.6
(2338 Ratings)
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V6035qwandreat
Oct 14, 2025
Andrea - Prague - Thanks to our wonderful, enthusiastic guide Gabriele, and our driver Mario our trip was a wonderful experience! The trip was very well organized - receiving messages throughout the day helped to keep the group together. Highly recommend!
Review provided by Tripadvisor
Mcbridespb
Oct 13, 2025
Full Day with Roberto, Flu & Reka - Full favour to 3 places along with an informative wine tasting session. Your leaders Roberto, Flu along with driver Reka. Went out of their way to make sure we enjoyed the day.
Review provided by Tripadvisor
Leongustavol
Oct 13, 2025
Great visit to Middle Ages! - Excellent visit to the medieval villages. Driver Reka, and tour leaders Roberto and Flu were extremely friendly and professional. With your guidance and help we were able to make the experience with tranquility and enjoyment.
Review provided by Tripadvisor
Miamiguy607
Oct 13, 2025
Packed day in Toscana. - Packed day with 4 stops… great explanations by Roberto. The day is short for all the activities planned by the tour, maybe too much for just one day. My favorite, Siena.
Review provided by Tripadvisor
Antoniot3506
Oct 13, 2025
EXCELLENT - Excellent work carried out by our driver, Reka, and our guides, Flu and Roberto. Thank you very much for your preparation and your work
Review provided by Tripadvisor
Samahs605
Oct 13, 2025
Wonderful Experience in Tuscany - This tour was amazing! Visiting Siena, San Gimignano, and Monteriggioni all in one day was perfect, especially under the guidance of Roberto and Flu, who were both very kind and helpful. Their knowledge and friendliness made the experience truly exceptional.
Review provided by Tripadvisor
Pabpab85
Oct 13, 2025
Excellent option to visit three key locations and of great interest in the Tuscan region. 100% recommended. - Excellent option to visit three key locations of great interest and beauty in the Tuscan region. 100% recommended.
Review provided by Tripadvisor
Jessica_m
Oct 13, 2025
We spent a day... - We had a great day with Sara, who was our guide. Although the trip was full day we did not have a great time as everything was very well organized. We had enough time to tour the three places calmly and even shop for regional wines and foods. He recommends the tour for anyone looking for a Spanish tour.
Review provided by Viator
Caralibroa
Oct 13, 2025
Oh, great. Very nice and well organized - All very well organized. Our guide Sara very friendly and very competent. All perfectly explained. The tour very complete although some time is missing in one of the villages. Outstanding
Review provided by Tripadvisor
141eduardom
Oct 13, 2025
A quick visit to Tusacana - Our guide Sarah was very friendly and knowledgeable about the region. We saw various parts of Tuscany, such as Monteriggioni, Siena and the impressive towers of San Gimignano. I recommend it as a family trip to relax and meet.
Review provided by Tripadvisor
From $76
up to 15 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).