Siena, San Gimignano, Monteriggioni and Chianti Wine Tasting Tour from Florence

Badge of ExcellenceFirenze, Italy
Likely to Sell Out

From $54.70

Select Date and Travelers

Free cancellation
Up to 24 hours in advance.
  • 10 hours 30 minutes (approx.)
  • Mobile ticket
  • Offered in: English


Combine medieval gems, fine wines, and UNESCO-listed monuments on this full-day tour of central Tuscany from Florence. Marvel over the medieval castle of Monteriggioni; explore the architectural wonders of historic Siena; and admire the striking skyline of hilltop San Gimignano. Enjoy Siena and finish your tour with a wine tasting at a local winery in the Chianti region.
  • Full-day tour of central Tuscany from Florence
  • Visit the UNESCO-listed towns of Siena and San Gimignano
  • See the magnificent Siena Cathedral and the medieval castle of Monteriggioni
  • Enjoy wine tasting in the Chianti wine region
  • Perfect introduction for first-time visitors

Sample Menu


Cheese, bruschette and cold cuts


Pasta with bolognese sauce or tomato sauce


Typical Tuscan biscuits

What's Included

  • Journey by fully-fitted GT Coach
  • Expert multilingual escort
  • Siena tour with professional guide (not included in the semi independent option)
  • Visit to a rustic wine estate in the Chianti area with wine tasting
  • Sampling of wines, extra-virgin olive oil and regional products
  • Free visit of San Gimignano and Monteriggioni
  • Gratuities
  • Hotel pickup and drop-off
  • Siena Cathedral tickets
  • Lunch

Meeting And Pickup

Meeting point

  • Piazzale Montelungo
    Piazzale Montelungo, Firenze FI, Italy

    TOURS & NEWS KIOSK AT PIAZZALE MONTELUNGO BUS TERMINAL Located at 5-10 minutes walking distance from Santa Maria Novella Train Station. Look for our staff wearing a FUCHSIA CIAOFLORENCE JACKET and holding a CIAOFLORENCE CLIPBOARD!

Start time

08:45 AM

End point

This activity ends back at the meeting point.

What To Expect

Additional Info

  • Confirmation will be received at time of booking
  • Not wheelchair accessible
  • A dress code is required to enter places of worship and selected museums. No shorts or sleeveless tops allowed. Knees and shoulders MUST be covered for both men and women. You may risk refused entry if you fail to comply with these dress requirements
  • May be operated by a multi-lingual guide
  • Please note that the given order of the visits may change
  • Stroller accessible
  • Service animals allowed
  • Near public transportation
  • Infants must sit on laps
  • Infant seats available
  • No heart problems or other serious medical conditions
  • Please inform us of any food intolerance or allergy in advance
  • 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, German, 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: GERMAN: Monday - min 2 pax FRENCH: Tuesday - Friday, min 2 pax PORTUGUESE: Wednesday - min 2 pax ITALIAN: Saturday, Sunday - min 2 pax
  • Travelers should have a moderate physical fitness level
  • This tour/activity will have a maximum of 63 travelers

Cancellation Policy

You can cancel up to 24 hours in advance of the experience for a full refund.

  • For a full refund, you must cancel at least 24 hours before the experience’s start time.
  • If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the experience’s start time will not be accepted.
  • Cut-off times are based on the experience’s local time.
  • This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.

Traveler Photos

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Traveler Tips

It is a full day tour with lots packed in - a great way of getting lots done on limited time.
Great locations, but really needed maps for pickup locations and getting around, especially when late at night /in the dark.
Maybe the wine even though enjoyable at lunch may not be necesssry as wine tasting that follows is very adequate .
717 reviews
Total review count and overall rating based on Viator and Tripadvisor reviews
Reviews by Viator travelers.
Showing 1-10 of 717 reviews
Good, skip guided Siena piece
Ashley_W, Mar 2023
Great way to see the countryside efficiently. If I went again, I'd skip the guided tour to get more independent exploring time in Siena. The wine tasting speaker was super engaging and fun, that space was also beautiful including many roaming chickens.
Step back in time and enjoy once medieval lands!
Christy_H, Mar 2023
Such a fun day to enter towns from medieval time periods. It was a long day, but a memorable one! There is a lot of walking and some of it is uphill- so be forewarned. My only other issue was this tour wasn’t specific to only English. So you heard 1 sentence in English and then the rest of the time was very verbose in 2 other languages. It made it a little hard. They saved the best (in my opinion) for last. San Gimignano was my absolute favorite. The views were spectacular. Such an incredible town! All in all, I would do this again.
Super nice trip.
Franois_G, Mar 2023
Nice guides (Constantino and Sarah): present, helpfully and historian. Bus driver Boris: smile bloody good driver. We had a very good trip.
Good day out.
Yolanda_B, Mar 2023
Great to see so much in one day in comfort and with free time to wander and soak up the atmosphere of such delightful places. Guide Stanislava was top class.
Very good day trip .
Maria_A, Mar 2023
This tour is fabulous, the winery was really good , and the places , I recommend, nice shoes to walk , there’s a lot up and down walking. The day we did the tour was a bicycle event. The tour guide Elizabeth was awesome 👏 and the bus driver .
There seemed to be a...
Chris_H, Mar 2023
There seemed to be a general lack of organization. There were issues with people changing seats on the bus and claiming they had reserved seats. None of this was addressed by the tour guide(s). The tour itself was fine and the sights are definitely worth seeing.
Response from Host, Mar 2023
Dear Customer, We are sorry to read that you have experienced some issues during your tour. Actually, we don’t think that this is a lack of organisation because all of our tours are well-structured and studied in detail to offer the best experience to all of our customers. We don’t reserve any seat on the bus, everybody can seat where they prefer but we kindly ask to not change it during the tour. Our tour leaders know very well these dynamics and they always try to prevent any discussion on board. Anyways, we are glad to read that you enjoyed the tour itself and the places you visited, that’s why we hope to welcome you again during your next trip to Florence and let you discover more about our wonderful region. We wish you a lovely day, Ciao Florence Staff
Best tour!
Simran_N, Mar 2023
Amazing guide! Best tour very well organised and planned 😊 explored 4 places in just 10 hours. Would recommend it to everyone!
Like stepping back in time…
Christine_M, Feb 2023
Tuscany is all we hoped it would be…like stepping back in time! Sarah was an awesome guide. The Duomo in Sienna was incredible. We would probably skip the Sienna tour and head straight to the church if we do it again. Our guide there did not have clear English and preferred to speak Spanish most of the time. Also, be prepared! No toilets were available on the bus, and not easy to locate on the tour. Having said that, we loved the day and highly recommend the tour.
Response from Host, Feb 2023
Dear Customer, Thank you so much for taking your time to leave us your feedback. We are sorry to read that you didn’t like the guided tour in Siena that much, we will forward your comment to the guide in charge as to let her improve her service. For safety reasons, toilets on the bus are not available: nobody can stand up or walk when the bus runs but for any need, passengers can ask the tour leader to stop and our staff will do their best to accommodate the request. We thank you again for your beautiful review and we hope to see you soon! Have a lovely day, Ciao Florence Staff
The best part was seeing...
Maureen_L, Feb 2023
The best part was seeing San Chimignano. Great town. The tour guide Constanio was fabulous and Max our driver was a happy guy. The thing I didn't like was the walking tour done by another guide, too much info and hard to understand, better to have done that ourselves.
Response from Host, Feb 2023
Dear Customer, Thank you so much for taking your time to leave us a review. We are glad to see that you enjoyed most of the tour and the company of Costantino and Massimo. In Italy we have two different licences, the one needed to be a tour leader, is different from the one needed to be a tour guide. That’s why Costantino couldn’t do the guided tour even if we are sure he would have loved to! Our guides are very informative and knowledgeable and they love to share all their knowledge with travellers. We also offer the semi-independent option (without guided tour). Maybe it would have been the best option for you… you can take it during your next trip to Florence! We hope to see you soon. Have a lovely day, Ciao Florence Staff
Great experience! Loved it!
ILIAS_K, Jan 2023
Sienna,San Giminiano are the highlights for sure, you are having a good taste/ feeling of Tuscany too.The wine tasting was interesting,I would like to see more of the procedure of the production.Mrs Roberta,our guide very polite,nice and informative.Appreciated her. The tour is about 10hours,not tiring at all.If I would change anything is one hour less at Sienna (we stayed 3h more) in order to visit another village ,representative of Tuscany
Response from Host, Feb 2023
Dear Client, thank you so much for your 5-star review! We are glad you enjoyed our activity and the company of Roberta. We are happy you chose us for your holidays and we hope to see you soon on your next trip to Florence! Have a lovely day, Ciao Florence STaff
Caring service
Franburnsmunro, Dec 2022
Tabitha was very responsive to individual needs, arranging a taxi when walking distances were long. The bus driver was excellent as well. Thank you both!
Siena Tour, part on your own, great bus tour, wine great, lots of fun and inspiration.
Louis_W, Dec 2022
The main sight we wanted to see in Siena was not on the scheduled stops for the in city-tour so we opted to take the “on your own,” choice for the tour. This provided us with bus transportation to/from Siena, a guide to get us to the meeting place, as some local information. Siena is hilly!!!! This is not a tour for the tired or mobility impaired. We had time to see St. Catherine’s church and museum and enjoy a nice lunch before meeting back up with the group. This worked perfectly for us. The winery was fine though we did not feel compelled to buy wine.
Great schedule to have 4 itineraries at one trip.
Hariyono_T, Dec 2022
It’s a nice experience to get a preview tour at Monteriggioni, Siena and San Gimignano. The wine tasting in Chianti is quite interesting if you are wine lovers. Otherwise it’s more like a product introduction , not the wine producing process.
Must do in Florence
Amy_L, Dec 2022
Like The castles, San Gimignano was great. The tour covered several places that worth visits. A long day but interesting.
A great day trip
Anl_T, Nov 2022
Definitely a worthy trip if you are in Florence and would like to visit some close cities of Toscany and have some wine tasting experience in Chianti region. Our guide Stefano was exceptionally good and managed to handle all the tour with a good time mamagement and accurate information and translation in 3 different languages.
Go for Siena, but don't book if you want a great vineyard and wine tour!
Stephanie_M, Nov 2022
I have done this tour several times with various family, friend and loved ones. The Siena, San Gimignano and Monteriggioni were fantastic, as was the guide, but the Chianti tour this time was terrible. We have been to some incredible vineyards in Tuscany as part of this tour for years, so I was so disappointed to be brought somewhere that was akin to a factory - and in a very flat part of what is a stunning and undulating part of Italy. The wines were terrible, we were shuffled in/out for an hour and it felt like a tourist trap.
Great trip
jeffbarron33, Nov 2022
Siena and San Gimignano were both great stops. The wine tasting was a little rushed. It was a full day of tours.
This WAS A FULL DAY ! and...
EC_M, Nov 2022
This WAS A FULL DAY ! and extremely enjoyable. Importantly, the tour got us into the smaller towns in Italy and gave us enough time to explore each of them. We found a wonderful, small, family owned/run restaurant in Siena with absolutely amazing food and service that treated you like family
Nice experience
July_F, Nov 2022
The tour was well organize. They even called us because we were to clise ti rhe time for the bus to leave. The guide guy was really funny .My favorite city was san giminiano(a true medivieal city and so pretty).
The cathedral in Siena...
Ron_P, Nov 2022
The cathedral in Siena and the tour there as well as the wine tasting. Both were exceptionally good. The medieval towns were a nice historical perspective. Thanks