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
4.5
(2008 Ratings)
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1 star
Mildred
Jul 28, 2025
One day 4 places. - Excellent guide to see several places in one day. If you follow the advice of the tour guide, you will enjoy the best of each place within the given timeframe.
Review provided by Tripadvisor
297amaias
Jul 27, 2025
Very entertaining family tour - Very entertaining and interesting tour, NO know makes heavy. Guides Gabriele and. Serene very willing and pleasant. DE wine tasting part we liked very much, and the local guide DE Siena deserves special mention. We repeat experience with them is worth it
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D5069ercarlosalberto
Jul 27, 2025
Amazing tour, amazing guides! - The trip was amazing! The guides Gabriel and Serena were attentive and on point with the times. Beautiful places and definetily worth for the price. The wine tasting experience is also a very nice plus. Just keep in mind you wont get to visit everything you want because of the times, specially for San Gimignano the free time felt very little and I would recommend extendig the visit to this town another 30 min, but otherwise a great experience.
Review provided by Tripadvisor
Pauhills
Jul 27, 2025
Full visit Tuscany - Very complete visit and very attentive and friendly guides (Gabrielle and Serena). It is worth looking at the time to choose a sunny day POR the views that are appreciated from the different villages.
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H7072mjphilipr
Jul 27, 2025
Great views - The tour guides were amazing. A big thank you to Gabrielle, Serena and Luca for such a great experience. The time in each town was so fun!
Review provided by Tripadvisor
283emmanuela
Jul 27, 2025
I recommend - Very good activity to visit some villages DE Tuscany. All well coordinated. The only recommendation would be to extend the visit to San Sigminiano.
Review provided by Tripadvisor
588hendras
Jul 27, 2025
Tuscany day tour - Amazing experience for our first time visiting Italy. We cover a lot Tuscany region in one day. Great job Gabrielle and Serena.
Review provided by Tripadvisor
Jose
Jul 27, 2025
SIENA MONTERREGIONI GIANTI SAN GIMINIANO - Magnificent tour POR Tuscany. Our guide Gabriele, Serena and Luca the phenomenal driver. A very pleasant day with a spectacular tour. Thank you very much to this great team. Highly recommended.
Review provided by Tripadvisor
Silviacw8327mr
Jul 26, 2025
Enjoyable trip - Very good tour organization, interesting information provided by the tourist guides, enjoyed the places. Special thanks to Alex!
Review provided by Tripadvisor
901zo_d
Jul 28, 2025
Buona scelta! - Well organized tour, enough free time at every visited place. It's been a pleasure to travel with Federico, who explained our route in detail. Thanks!
Review provided by Tripadvisor
From $75
up to 15 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).