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
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
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
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 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 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
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
2,663 reviews
Total reviews and rating from Viator & Tripadvisor
Ryan H,Mar 31, 2026
- Review from Viator
Excellent value and informative trip through Tuscany. Sienna was the true highlight with a knowledgeable local guide and plenty of time to wonder around. Wine tasting was fun and the two stops for the fortress were just awesome.
71gonzaloe,Mar 31, 2026
- Review from Tripadvisor
It was a very god experience, I go to 4 stops and I hace a great time.
Christene d,Mar 31, 2026
- Review from Viator
Bus clean and comfortable enough for a full day touring into Tuscany. Our bus had half English and half Spanish speaking so our guide repeated for both languages with his Spanish being significantly better than his English. The drivers skills and care was excellent. The walking tour in Siena was fine, although despite headsets provided cracked and was difficult to hear the majority of the time unless you were close to the guide and could hear her normal speaking volume. San G. Was a disappointment...the guide said follow me to a nice view but walked quickly through the crowd without care to know who was able to stay with him. It would have been nice to have some information about the location, but minimal was offered. The wine tour and balsalmic tasting for the day was entertaining. I dont think anyone bought much of anything as the wines, although were fine, were expensive at 60 Euros or more per bottle.
fabiennek874,Mar 30, 2026
- Review from Tripadvisor
Big thank you to our wonderful and amazing guides, Sarah and Francesco. Very attentive, ready to answer all questions and presentations onboard really clear, fun and well detailed. Sarah really made contact with everyone and made sure we were making the most of the day. Never felt pushed, just sat back, relaxed and let ourselves be guided. THANK YOU 🤩 Fabienne and Ian Kitson
paullJ1327GO,Mar 30, 2026
- Review from Tripadvisor
What an amazing day !!! Pack full of great sights and adventure. We never felt rushed and had plenty of time to sample the places we visited. The ability to either join a guided tour, or wander off on our own was greatly appreciated. Sara, Francesco were brilliant. Always there to help, and full of really interesting facts about the region. They did a stunning job of bringing the tour to life. Reka our driver did a brilliant job getting that huge bus through some very tight village streets. We always felt safe. Well done to all three as they added an extra dimension to the tour that would have been missing if we had just done it on our own.





Dorota P,Mar 30, 2026
- Review from Tripadvisor
Sara, Francesco and Reka were fantastic, the trip was well organised and all went smoothly.




879geetanjalij,Mar 30, 2026
- Review from Tripadvisor
I had an incredible experience on my tour to Chianti, San Gimignano, and Siena with Ciao Florence. My guides, Sara and Francesco, along with our driver, Reka, were fantastic and made sure I was well-cared for the entire day. The tour was conducted in both English and Italian, and it was very informative. I really appreciated how friendly the team was and how they balanced the history of these beautiful locations with plenty of time for me to explore on my own. The wine tasting was a major highlight… excellent wine and a great atmosphere. I had a wonderful time and highly recommend this team if you want a professional, fun, and seamless tour of Tuscany!





473cherip,Mar 30, 2026
- Review from Tripadvisor
Sara and Francesco were great guides. Cannot imagine being a tour guide in two Languages but Sara does it with such grace. Was a fun day that passed too quickly. My only concern was not enough time in San Giamangnano. Felt very hurried as our last stop of day. A reason to return. 🇮🇹


C4983WBadamg,Mar 30, 2026
- Review from Tripadvisor
We had a wonderful time. San gimaniano was a highlight. Thank you Sarah and Francesco. Your organization, energy and communication helped make our day. Thank you.
Happiness41733143500,Mar 30, 2026
- Review from Tripadvisor
We had an absolutely wonderful day in Siena – thank you so much to Sara, Francesco, and Reka! ❤️ Everything was perfectly organized, and you could really feel the passion and care you put into the experience. The atmosphere was relaxed, informative, and at the same time very enjoyable. We not only visited beautiful places, but also learned a lot and felt very well taken care of throughout the day. You truly made this day something special, and we are very grateful for that. We highly recommend this experience to everyone and would love to join you again anytime. Grazie mille and hopefully see you again soon! 🇮🇹
-25% off
From €48.75Was €65.00
Operated by Ciao Florence Tours Srl