Siena, San Gimignano and Chianti Wines Day Tour from Florence
Overview
Available languages
10 hours 30 minutes
Mobile ticket
A full day tour, taking in the key beauties of Central Tuscany including a delicious Chianti wine tasting. You'll roll through the sweeping countryside to arrive at the jewel of Siena, with its unique Square and Gothic Town Hall. Then you'll take the road for San Gimignano, the Medieval New York, and Monteriggioni - a hilltop castle with breath taking views. But it's still not over! End your visit with a Chianti winery where you savor the best of Italian wines. This is a perfect day-out to relax and replenish your spirits.
Additional Info
Infants and small children can ride in a pram or stroller
Public transportation options are available nearby
Infants are required to sit on an adult’s lap
Specialized infant seats are available
Not recommended for travelers with poor cardiovascular health
Travelers should have at least a moderate level of physical fitness
May be operated by a multi-lingual guide
Please note that the given order of the visits may change
Kindly note that the Semi independent option does not include the professional guide in Siena
LOW SEASON (From November, 1st until March, 31st): English and Spanish languages are always guaranteed. In order to confirm the excursion in French, Italian or Portuguese a minimum of 4 pax is required
HIGH SEASON (From April 1st until October 31st): this tour is always available in English and Spanish. Other languages are confirmed as follows: FRENCH: Tuesday - Friday, min 2 pax PORTUGUESE: Wednesday - min 2 pax ITALIAN: Saturday, Sunday - min 2 pax
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
What To Expect
There is no time to waste when exploring the stunning Tuscany hills! Meet your tour guide at Piazzale Montelungo Bus Terminal early in the morning. Piazzale Montelungo is located 5-10 minutes walking distance from the Santa Maria Novella train station. Hop on the comfortable coach bus, choose your seat, and relax before departing on your journey! The drive to Monteriggioni will take about one hour. During the journey, your guide will entertain you with plenty of interesting information about Tuscany and its sights on the way. Upon arrival, your expert guide will share some interesting information and fun stories about Monteriggioni! If you have any questions, your guide will be there to assist you.
Monteriggioni
After about 40 minutes by bus, arrive in Monteriggioni, a charming medieval fortress set atop a hill. Enjoy 45 minutes of free time to stroll through the village squares and soak up its timeless atmosphere. Guests may also choose to walk along the fortress walls (optional, extra cost).
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)
Gratuities
Hotel pickup and drop-off
Siena Cathedral tickets (approx. 7€ pp)
Lunch
Options
French With Guided Siena
All inclusive tour in French: Including 1 hour guided tour in Siena, Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery
Spanish With Guided Siena
All inclusive tour in Spanish: Including 1 hour guided tour in Siena, Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery
Italian With Free Time
What is not included: Local Guide in Siena. What is included: Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery
English With Guided Siena
All inclusive tour in English : Including 1 hour guided tour in Siena, Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery
Portuguese With Guided Siena
All inclusive tour -Portuguese: Including 1 hour guided tour in Siena, Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery
French With Free Time
What is not included: Local Guide in Siena. What is included: Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery
English with Free Time
What is not included: Local Guide in Siena. What is included: Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery
Italian With Guided Siena
All inclusive tour in Italian: Including 1 hour guided tour in Siena, Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery
Spanish With Free Time
What is not included: Local Guide in Siena. What is included: Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery
Portuguese With Free Time
What is not included: Local Guide in Siena. What is included: Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery
Reviews
2,632 reviews
Total reviews and rating from Viator & Tripadvisor
Outstanding Experience
Newman M,Mar 22, 2026
- Review from Viator
5.00John 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.
Wonderful tour
565andan,Mar 21, 2026
- Review from Tripadvisor
5.00Our 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.
Wine and San Gimignano! What more could you ask for?
841brads,Mar 20, 2026
- Review from Tripadvisor
5.00Excellent 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.
Really good
dionisiap957,Mar 20, 2026
- Review from Tripadvisor
5.00It was a really nice experience! Can and Chiara our guides were really helpful and kind! Thank you for making our experience so memorable!
Really good
dionisisv559,Mar 20, 2026
- Review from Tripadvisor
5.00Was a really nice experience Jan and Kiara was the best guides
Great!
Wander58671671585,Mar 20, 2026
- Review from Tripadvisor
5.00Great excursion. John and Kierra were very organized and attentive leaders. Mario was a great and efficient driver. Recommend this 100%
Good for getting to know Italian Tozcana
miriamcV0NU,Mar 20, 2026
- Review from Tripadvisor
5.00It was a punctually organized trip, maybe it would be good to add a little more time as sometimes it felt very rushed but overall a very good experience.
Great experience
Courtney B,Mar 20, 2026
- Review from Tripadvisor
5.00Great tour with a great team. John and Chiara were very knowledgeable and kept the group on track. We had the perfect amount of time in each location but never once felt rushed. Would definitely consider other tours from this group in the future!
Excellent experience
J3990FXrebeccab,Mar 19, 2026
- Review from Tripadvisor
5.00Great tour! There was a good balance between time spent with the tour and time spent walking around on our own. I was impressed that the bus driver was able to get through some of the tight turns.
Good.
mariamQ3805RV,Mar 19, 2026
- Review from Tripadvisor
4.00All very well, except the guide to Siena that we did not like your explanations It has nothing to do with Fabien who did super well.
-25% off
From €48.75Was €65.00
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Operated by Ciao Florence Tours Srl