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.
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
For a full refund, cancel at least 24 hours before the scheduled departure time.
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).
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
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
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
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
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
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
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
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
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
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
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
2,569 reviews
Total reviews and rating from Viator & Tripadvisor
Guzmanniembro,,Feb 22, 2026
- Review from Tripadvisor
Wonderful trip that everyone should do. Very comfortable and unforgettable thanks to Roberto (the driver) and Gabriele, who gave us tips and useful information to enjoy everything the most





nadiadP7105XI,,Feb 22, 2026
- Review from Tripadvisor
We had an absolutely wonderful day tour from Florence to Siena, San Gimignano, Monteriggioni, and Chianti with Ciao Florence. Everything was perfectly organized from start to finish, and the entire experience exceeded our expectations. A special thank you to Gabriele, who was an incredible guide — knowledgeable, engaging, and genuinely passionate about the history and culture of Tuscany. He explained everything in such an interesting and easy-to-follow way, and she made sure everyone felt included and comfortable throughout the day. Also, a big shoutout to Roberto, our driver, who was fantastic. He navigated the Tuscan roads smoothly and safely, allowing us to relax and enjoy the stunning countryside views. His professionalism and calm driving made the trip even more enjoyable. The towns were breathtaking, the wine tasting in Chianti was a highlight, and the overall pace of the tour was just right — enough time to explore while still seeing so much in one day. I highly recommend this tour and especially hope you’re lucky enough to have Gabriele and Roberto as your team. Truly a memorable experience in Tuscany!
130giorgosm,,Feb 22, 2026
- Review from Tripadvisor
Very cool good driver Roberto
Veronique M,,Feb 22, 2026
- Review from Tripadvisor
Great tour. Enough time at every place. Generous with tasting wine. Tour was bilingual English and Spanish. Roberto the driver was good and Gabriele the guide was also nice. Good value for Money. Book thru Booking and even got a last minute discount. Recommended.







aliza1063,,Feb 22, 2026
- Review from Tripadvisor
Loved the tour! I made lots of friends and the wine was delicious. San Gimingnano is gorgeous at sunset.
jwr12345,,Feb 20, 2026
- Review from Tripadvisor
John ran a perfect full day intense tour smoothly in 3 languages. He managed the large group so well, there were zero issues. Everything like clockwork. I can’t believe how much sightseeing was accomplished in just one day. 3 historic Italian cities and a charming winery. Money well spent. I loved the tour. Thanks John

Y7324PZderekw,,Feb 20, 2026
- Review from Tripadvisor
The leader of the team John is very responsible for English, Western, French in three languages, very good and kind, the package of trips San Gimignano, Siena is great, the wine trips are good, but go to this wine at about 4-50 euro per drink, I feel biased, not sure if the price is universal. Just San Gimignano arranged in the end not sure is a good plan, because the sky is dark seems a bit unfortunate, but you can see the late sunshine (if the weather is good),





Jwebster321,,Feb 20, 2026
- Review from Tripadvisor
We spent the day touring Tuscany with our Tour guide John. It was a great day. John was very knowledgeable and spoke in 3 languages perfectly. He was very helpful and answered all our questions. I would highly recommend John and this tour!
F5723VFbrittanyt,,Feb 20, 2026
- Review from Tripadvisor
Jonn was a wonderful guide, he went above and beyond to make sure we were well taken care of. His language skills are incredible and it was perfectly easy to understand his explanations. Thanks Jonn!
160elinep,,Feb 20, 2026
- Review from Tripadvisor
Very nice excursion only the last one was a bit long. Our John Guide was pleasant and interesting.
-25% off
From €48.75Was €65.00
Operated by Ciao Florence Tours Srl