San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting
Overview
Available languages
11 hours
Mobile ticket
Discover Tuscany in one day from Florence. Begin in the hilltop UNESCO town of San Gimignano with about 2 hours of free time to explore towers, lanes, and artisan shops. Continue to Monteriggioni (seasonal; see note), a perfectly preserved walled village, with time to wander inside the walls. Cross the rolling Chianti hills to a cozy winery for a tasting of three wines and a three-course farm-to-table lunch, ending with cantucci & vin santo. In the afternoon, enjoy a guided walking tour of Siena: stroll Piazza del Campo and see the Palazzo Pubblico, then admire the Cathedral (interior visit if option selected). Finish with free time before returning to Florence.
Please note that the order of the visits may change
(*) November to March, the Tour does not include the stop at Monteriggioni and the return to Florence is approx 30 minutes earlier
Additional Info
Infants and small children can ride in a pram or stroller
Public transportation options are available nearby
Specialized infant seats are available
Travelers should have at least a moderate level of physical fitness
A dress code is required to enter places of worships and selected museums. No shorts or sleeveless tops are allowed. Knees and shoulders MUST be covered for both men and women. This dress code is strictly enforced and you will risk refused entry if you fail to comply with requirements.
For small groups, up to 8 pax, the Tour escort service could be replaced with an English speaking driver-guide service, while maintaining unchanged the entire program of the excursion.
Comfortable walking shoes are recommended.
From November to March, the itinerary does not include the stop at Monteriggioni and the return to Florence is approx 30 minutes earlier
It is mandatory to arrive at the meeting point at the mentioned check in time. In case of delay or no show it will not be possible to join the tour, nor to have a refund or reschedule the tour.
Please be advised that it is required to bring your original ID with you during the tour.
Once the audio guides are handed over before the guided tour, they become the full responsibility of the customer. In case of loss, a fee of €80 will be charged.
Clients with motor disabilities or wheelchair users are encouraged to notify the tour organizer in advance and seek medical advice to ensure suitability of services. Our tours and transportation are not suitable for people with motor disabilities or wheelchair users, so to prioritize the safety and well-being of all involved, the driver and tour manager retain the right to decline participation if they believe it may compromise safety. This decision rests solely with them, and no compensation will be provided in such cases. By accepting these terms, clients agree to respect decisions made by staff regarding participation.
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
What‘s Included
Licensed Tour Escort for on-board insights and coordination
If option selected: Skip-the-line access to visit inside Siena Cathedral & Piccolomini Library
If option selected: from April to October monolingual guided visit in Siena
Wine tasting: three Chianti wines plus traditional vin santo
If option selected: Guided walking tour of Siena with a professional local guide
Chianti winery experience: guided cellar & vineyard visit plus 3-course Tuscan lunch
Assistance by Caf Tour Team at the meeting point
Round-trip transport by comfortable, air-conditioned coach from Florence
Our Shared Round Transport option does NOT include: Siena Guided Visit, Cathedral admission
From November to March, the itinerary does not include the stop at Monteriggioni
What To Expect
San Gimignano
Discover the UNESCO-listed “town of towers,” a perfectly preserved medieval hilltop gem with panoramic views, artisan boutiques, and photogenic alleys. Enjoy ample free time for your own exploring, from award-winning gelato to snapshots of the skyline—ideal on a day trip from Florence.
Piazza Della Cisterna
The atmospheric heart of San Gimignano, framed by tower-houses and a medieval stone well that anchors the square. A short, curated stop for photos and storytelling that brings the town’s merchant past to life.
Options
Tour in English
Lunch
Shared Day Trip from Florence: It includes: Siena Guided Visit, Lunch and wine tasting, Transport, Tour Leader on board.
Not included: Cathedral admission
English Tour with Cathedral
Lunch
Siena Cathedral Visit included: It includes: Transport, Tour Leader on board, Typical Lunch, Siena Guided Visit and Cathedral admission
Spanish Tour with Cathedral
Lunch
Siena Cathedral Visit included: It includes: Transport, Tour Leader on board, Typical Lunch, Siena Guided Visit and Cathedral admission
Spanish-Shared Round Transport
Lunch
Shared round Trasport & Lunch: It includes: Transport, Tour Leader on board, Typical Lunch.
Not included: Siena Guided Visit and Cathedral admission
Tour in Spanish
Lunch
Shared Day Trip from Florence: It includes: Siena Guided Visit, Lunch and wine tasting, Transport, Tour Leader on board.
Not included: Cathedral admission
English-Shared Round Transport
Lunch
Shared Round Transport & Lunch: It includes: Transport, Tour Leader on board, Typical Lunch.
Not included: Siena Guided Visit and Cathedral admission
Reviews
4,391 reviews
Total reviews and rating from Viator & Tripadvisor
Well worth doing especially if you like History & Wine
475KateH,
Nov 12, 2025
- Review from Tripadvisor
5.00Loved this tour the places we visited were amazing and you had plenty of time to yourself. I like doing the guided tours as I like to hear the history. There is a bit of walking involved getting to the meeting spots which needs to be taken into account if you have any issues. it's a full day tour and i can't thank our guide Frederick and driver Hamil enough it was a lot of driving and a decent size group to manage.
Amazing day
Kylie D,
Nov 12, 2025
- Review from Tripadvisor
5.00Amazing visit to some beautiful towns. Lunch at the winery was great. Our guide, Sandro was absolutely fabulous and very knowledgeable.
Not what we expected
Carmen G,
Nov 11, 2025
- Review from Viator
3.00The visit to San Gimignano was phenomenal. Wine tasting and nothing special: right antipasti, small plate of macaroni and dessert practically non-existent. The guided tour option to Siena was the worst: short tour with poor explanation. We took the option of the cathedral and the explanation of the guide did not exceed 10 minutes. In short, we were disappointed. The tour guide if that was okay. She looked expert and gave us many explanations
Great company for day tour of Tuscany
ceb325ny,
Nov 9, 2025
- Review from Tripadvisor
5.00Great day trip of the best towns in Tuscany and fun vineyard lunch stop. Sandro was an excellent tour guide and the value for this package is great.
Exceptional experience
Thomas B,
Nov 7, 2025
- Review from Viator
5.00Sandro was great as our guide for all our destinations today! Highly recommend and lucky to get him!
A wonderful day trip to experience Tuscany
carolynw494,
Nov 6, 2025
- Review from Tripadvisor
5.00This tour more amazing than we could have expected. San Gimignano was magical, the wine tasting and lunch was perfect, and Siena was enchanting. Our guide Sandro made it so enjoyable with his wit, knowledge, and professionalism. We were in awe with his multilingual skills! And our driver Alessandro was wonderful, taking us to all of our destinations in a safe, smooth, and timely manner.
Worth the ride
Wayne B,
Nov 3, 2025
- Review from Viator
4.00Excellent tour guide (Ricardo) and driver, Alessandro. It was a long day for sure but worth the ride!
Fun in Tuscany
Daniel G,
Nov 2, 2025
- Review from Viator
5.00Ricardo, Alisandro and his team were fantastic. Ricky knew his stuff inside and out, was genuine, funny, engaging and very pleasant to be around all day. Alisandro was fantastic behind the wheel all day without a hiccup. Thanks for the fantastic day.
Interesting and tasty experience in Tuscany
guido mitolo,
Nov 2, 2025
- Review from Tripadvisor
5.00Anyone should at least take a day trip to visit the region of Tuscany. This day trip is worthwhile. The tour guide, Ricardo, is knowledgeable, easy to understand, and funny. The driving is safe and comfortable. In each visit, we had enough time to appreciate the views. The lunch stop was very complete. We drank a lot of wine of different types, and the food was plenty. I recommend this trip.
Good in Tuscabny
Joan M,
Nov 2, 2025
- Review from Tripadvisor
4.00Ricardo & Alex were excellant. The inntinery was well planned . The guide in Siena was hard to hear and understand . Enjoyed the lunch. Highly reccomend.
From €79.00
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