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
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)
Journey by fully-fitted GT Coach with Free Wifi on board
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
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
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
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
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
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
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
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
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
Reviews
2,537 reviews
Total reviews and rating from Viator & Tripadvisor
My first time to Italy and the first time to join a one-day journey group, it’s unexpected wonderful and guide is nice
423wud,,Feb 7, 2026
- Review from Tripadvisor
5.00The Monteriggioni in the morning is quiet and cozy,I like its outlook,it’s just like a crown on the top of the mountain.As to Siena I hope next time it can defeat the Firenze hahaha just kidding.But the best sight seeing must be the San Gimignano in the evening I love it so much! Unexpected wonderful journey in Italy,thanks a lot Ciao Florence!
Wonderful tour - would book again
Z9053SHsarahl,,Feb 7, 2026
- Review from Tripadvisor
5.00Frederica did a fabulous job leading the tour to Siena, a winery, and two medieval villages. She had excellent tips for shopping, where to eat, and what to try in each region. There was plenty of time for each stop.
The best culture and people in all my trip
g nesisd2026,,Feb 7, 2026
- Review from Tripadvisor
5.00Was an amazing experience, Federica is such an incredible person and a pretty good guide, she was so pacient and helpfull in all the experience! I would repeat it as much as I can. Was my first time in Italian tuscany and I've adore it a lot
Great Experience!
mfer20,,Feb 6, 2026
- Review from Tripadvisor
5.00The tour shows amazing places and small villages from the Toscana. The tour guide Federica was amazing and friendly, she explained very well with details the places , food and history. I totally recommend this tour!
A Delightful Day!
Ellen D,,Feb 6, 2026
- Review from Tripadvisor
5.00What a perfect way to spend a day! Each stop was scenic and informative, and our guide Federica was just lovely — so interesting and energetic.
Winery Tour in the Rain
NorthStar18627837518,,Feb 4, 2026
- Review from Tripadvisor
5.00John, I know it's been hard. Thank you for your hard work. The Japanese guides have been very kind to me and helped me a lot! Thank you very much.
Too fast
Clayton W,,Feb 3, 2026
- Review from Viator
3.00Too fast in Sienna, the tour guide spoke too fast & walked just as fast. San Gianomo was great & the winery.
Simply fantastic
Ivan S,,Feb 3, 2026
- Review from Viator
5.00Our guide Constatino was just brilliant. We crammed everything in... And more!!! Instructions beforehand were 5*, would definitely book with them again, thank you
Winter, Off Season Visit to Tuscany Is Great
jeanwK8272TN,,Feb 2, 2026
- Review from Tripadvisor
5.00The tour was well paced and relaxed, no rush with plenty of time to explore the areas visited. Cecilia, the guide, did a great job!
Must Book
priyankad594,,Feb 2, 2026
- Review from Tripadvisor
5.00The day tour was simply amazing at this season. Our tour guide as well as the driver did a fantastic job. Absolutely love it !
From €65.00
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Operated by Ciao Florence Tours Srl