Tuscany Tour: Explore Siena and Chianti Wines

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
  • Piazzale Montelungo - Begin your adventure through the breathtaking Tuscan hills without delay! Meet the tour guide at Piazzale Montelungo Bus Terminal early in the morning. This location is conveniently situated just a 5-10 minute walk from the Santa Maria Novella train station. Board the comfortable coach bus, select your seat, and unwind before…
What's Included
  • Free time in San Gimignano and Monteriggioni Medieval towns
  • Gran Turismo Luxury bus travel with WiFi on board
  • Expert multilingual Tour Leader
  • Visit to a charming Chianti wine estate with tastings of up to 2-3 Chianti wines and regional snacks
  • Siena tour with professional guide with Headsets (not included in the ‘+ Free Time’ option)
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
(2626 Ratings)
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610siddharths
Mar 24, 2026
Great day with best driver and guide - Great trip if you want to cover a lot in one day ! Roberto and Renaldo were great ! I recommend the trip if you want to explore Tuscany and don’t have a lot of time.
Review provided by Tripadvisor
Newman_m
Mar 22, 2026
Outstanding Experience - John Marcco was our guide and he was outstanding. Ever location was so wonderful. I'd recommend adding the lunch to the tour. The tour was better than expected highly recommend. The best way to see Tuscany when you only have a day our two in the area.
Review provided by Viator
Eliane
Mar 21, 2026
Great walk - Nice walk. A little runny but well worth it. The guides were great. The bus very comfortable. I recommend
Review provided by Viator
565andan
Mar 21, 2026
Wonderful tour - Our experience with Ciao Florence to visit Siena, San Gimignano & Chianti Wine Region was truly wonderful and exceeded expectations from start to finish. The itinerary was perfectly curated, combining culture, history, and relaxation in a seamless way. Special thanks go to our guide Gianmarco who was friendly, organized, and very informative throughout the day and the bus driver Renaldo, whose proffesionalism and smooth driving made the journey comfortable and stress-free. Overall, this tour was a perfect blend of sightseeing and authentic Tuscan experiences. We would highly recommend this agency to anyone looking to explore the region in a comfortable and memorable way.
Review provided by Tripadvisor
841brads
Mar 20, 2026
Wine and San Gimignano! What more could you ask for? - Excellent tour! The wine tasting was a highlight. Such wonderful wines and a great presentation by the producer. John and Kiara were excellent tour guides. They interacted with the group and made you feel comfortable and safe at each destination. So wonderful to have multilingual guides as well. San Gimignano was also another highlight. Such a beautiful unique town with the high houses. Something everyone should see. I highly recommend this tour.
Review provided by Tripadvisor
Dionisiap957
Mar 20, 2026
Really good - It was a really nice experience! Can and Chiara our guides were really helpful and kind! Thank you for making our experience so memorable!
Review provided by Tripadvisor
Dionisisv559
Mar 20, 2026
Really good - Was a really nice experience Jan and Kiara was the best guides
Review provided by Tripadvisor
Coastal60936125784
Mar 20, 2026
Great day with marvelous guides - Great day visiting charming towns together with wonderful guides John and Chiara and driver Mario. Thank you very much to the 3!!
Review provided by Tripadvisor
Wander58671671585
Mar 20, 2026
Great! - Great excursion. John and Kierra were very organized and attentive leaders. Mario was a great and efficient driver. Recommend this 100%
Review provided by Tripadvisor
Charlie_m
Mar 24, 2026
Well organized and... - Well organized and professionally run by Roberto and his crew. Was a long day to manage and you could tell they’ve done it many times.
Review provided by Viator
From $75
up to 15 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).