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
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 Italian: Including 1 hour guided tour in Siena, 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
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
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 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
2,484 reviews
Total reviews and rating from Viator & Tripadvisor
N8215GYroberta,,Dec 31, 2025
- Review from Tripadvisor
Wonderful job to Claudia, Anastasia, Boris, and John. All of the staff were true professionals and the tour was very relaxing with no stress.
T9849KBsergiog,,Dec 29, 2025
- Review from Tripadvisor
Very good experience, we made a very special trip my mother, my sister and I. To say that for me, it has been one of the best experiences of the whole trip. John has been wonderful with everything, attentive, friendly and dedicated throughout. I recommend the experience to everyone.
Q97YJpamelar,,Dec 28, 2025
- Review from Tripadvisor
The tour was beautiful, we met divine places and ate delicious. Emma and lucia were excellent guides Recommended 100%.
kyriakosr2017,,Dec 27, 2025
- Review from Tripadvisor
Beautiful trip!The wine tasting surprised us positively! To San Gimignano beautiful (we would prefer less time in Siena and more in san gimignano).Our guide prudent, transported us safely,our guide Gabriele very kind and willing to give a lot of information throughout the trip.Thank you! Tip: if you book the tour a day before it makes a good discount (online) 😉
SunitaD97,,Dec 27, 2025
- Review from Tripadvisor
Thoroughly enjoyed the day trip to Tuscany. The scenic beauty of the rolling hills and vineyards was absolutely breathtaking. The drive was amazing with our bus driver Rinoldo on the wheels and our guide Gabriele provided fascinating insights into the local culture and history. The wine tasting experience was a delightful highlight, offering a true taste of the region. It was an unforgettable experience and highly recommend to anyone visiting the area.
ioannac491,,Dec 27, 2025
- Review from Tripadvisor
The tour was amazing!! It's worth if you want to have a true experience in Tuscany. Also, the tour guide and the driver were very helpful!! Our favorite place was the wine tasting



luciadM2674TM,,Dec 27, 2025
- Review from Tripadvisor
Beautiful experience, very complete tour. The guide and equipment very clear and friendly. I recommend hiring the tour. Beautiful landscapes



Cecilia N,,Dec 26, 2025
- Review from Tripadvisor
Great tour by John and Sara. Very organized and informative. Recommend for everyone who would like a day trip from Florence
K6746IH ,,Dec 26, 2025
- Review from Tripadvisor
Beautiful day. From the beginning everything was so clear, the schedule, the plans, the rules. Great guides John and Sarah!
lyndalY2503YA,,Dec 21, 2025
- Review from Tripadvisor
Lucy and crew were wonderful! We had a great experience And enjoyed the historical guided tour! We would recommend highly!
Operated by Ciao Florence Tours Srl