San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting

Firenze, Italy

From $62.66

Select Date and Travelers

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


See the Tuscan gems of San Gimignano, Siena, and Chianti on a day trip from Florence. Stop first in the city the medieval hilltop town of San Gimignano. Then it is time for a stop at a Chianti winery for a typical lunch which includes guided wine tasting and “vin santo." Top off your trip in Siena to explore its historic city center with a stop at the Duomo.
  • Travel through the Chianti countryside in Tuscany
  • Explore Siena's Old Town with your guide
  • Discover the famous Siena Cathedral and its treasures
  • Enjoy a guided tasting and lunch at a Chianti Winery

What's Included

  • Transport by G.T. air-conditioned coach with WIFI on board
  • Licensed Tour escort with live commentary on board
  • Guided Visit in Siena with professional local Guide
  • 3 course typical Tuscan lunch in a Chianti Winery
  • Tasting of three different Chianti Wines, extra virgin olive oil, balsamic vinegar & “vin santo”
  • from April to October - monolingual Visit in Siena
  • If Option selected: Siena Cathedral interior Guided Visit including entrance fee
  • Our semi-independent option includes: Transport-Tour escort on Board-Typical Lunch
  • Our semi-independent option does NOT include: Siena Guided Visit, Cathedral admission

Meeting And Pickup

Meeting point

  • Piazzale Montelungo
    Piazzale Montelungo, Firenze FI, Italy

    Check in time: 07:45am - Montelungo Square, at the end of the ramp connecting with the train station. An assistant will be waiting for you wearing blue clothing with CAF Tour - Gray Line logos.

Start time

08:00 AM

End point

This activity ends back at the meeting point.

What To Expect

Depart from central Florence and ride south through the Tuscan countryside by coach.

After a scenic drive past the vineyards, arrive in San Gimignano, a medieval hill town best known for its impressive towers and frescoes. Soak up some free time to explore its streets independently before heading to Monteriggioni for a short visit.

Then it's on to the charming village of Chianti for a visit to a hilltop winery. Sit down and sample fine local wines, accompanied by snacks before tucking into a 3-course Chianti-style lunch.

Finally, head to Siena and admire the Renaissance artwork inside with your guide before taking off on a walking tour. Take note of the uniquely striped marble of the Siena Cathedral and, if you've upgraded, head inside for a guided tour.

Your trip concludes with transportation back to Florence.

Please note that the order of the visits may change.

Historic Centre of San Gimignano

Your memorable journey starts with the charming San Gimignano, world famous walled town located on a hilltop, which remained intact through the centuries, renowned for its tall towers, wonderful frescoes and many other valuable works of art: here the tour leader will lead you to the historical center, where you will have around 2 hours of free time for a fascinating discovery.

2 hours Admission Ticket Free

San Gimignano Bell Tower

the charming San Gimignano, world famous walled town located on a hilltop, which remained intact through the centuries, renowned for its tall towers, wonderful frescoes and many other valuable works of art

5 minutesAdmission Ticket Free

Additional Info

  • Confirmation will be received at time of booking
  • 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.
  • Not wheelchair accessible
  • Stroller accessible
  • Near public transportation
  • Infant seats available
  • 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
  • Travelers should have a moderate physical fitness level
  • This tour/activity will have a maximum of 50 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 a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund.

Traveler Photos

See more

Traveler Tips

Make sure you know exactly where the tour leaves from as signage is poor.
First stop was San Gimignano, which by itself would be worth the trip.
The group was small which made it easy to organise everyone and minimised waiting times.
1,972 reviews
Total review count and overall rating based on Viator and Tripadvisor reviews
Reviews by Viator travelers.
Showing 1-10 of 1,972 reviews
Excellent day trip, would highly recommend.
GERALD_M, Mar 2023
Excellent day trip and the two guides Sandro and Lisa were superb. would definitely recommend this trip. A most enjoyable day and the wine tasting lunch was very good.
Excellent day to explore Tuscany
Jennifer_S, Mar 2023
I thought my tour guide, Maria Louisa, was wonderful. She was knowledgeable and skillful at wrangling our group. It was such a pleasant way to spend the day. The tour bus was comfortable and I really loved the free time to explore San Gemignano. FYI - go ahead and book the guided tour of Siena. It's well worth it. If I have a quibble, it's that you don't actually go to Monteriggioni (you drive by it quickly on the highway). The winery tour and tasting with lunch was fantastic.
An excellent tour
Jeremy_P, Mar 2023
A really excellent and well organised tour which let me take in San Gimignano dying a quie time. Wine tasting and lunch memorable and Siena tour guide knowledgable and very informative
Wonderful day in Tuscany
Jillian_D, Mar 2023
My group of 19 friends loved this trip! The pace was perfect, our time in each city was nice, and the lunch was delicious. Constantino was very friendly and knowledgeable. He worked hard to make sure we had a good time. The bus was clean and comfortable, and I was surprised how smoothly the day went with the total size of our tour group. I would highly recommend this tour - for many of my 19, this was a favorite day out of our week long trip to Tuscany.
Wonderful Day!!
Jennifer_F, Mar 2023
So glad we did this tour!! We learned so much more than we anticipated and enjoyed every moment. Our guide Sandro (sp?) was incredible!!! He was personable, fun, knowledgeable and impressively engaging in all 4 languages represented in our group. What a fantastic way to see some parts of the country we might have otherwise missed!
Great Tuscan Day Out
Susan_R, Mar 2023
Stunning places we visited on trip.Great tour guide Mark(Marko?) Great value for money. We had great weather which helped.We could relax,everything done for you on trip.Coach very comfortable.
The tour outshined the rain!
Darryl_B, Mar 2023
A warm cappuccino to great us out of the cool weather. Visiting a linen vendor, buying some fabric and hearing his story. We had a great time at the wine tasting. Met 6 new friends! We walked talked with our new friends around Siena. Our guide in Siena was Nicoletta. She was very knowledgeable about Siena, as she was a lifetime local. She highlighted the Palio in the Il Campo. Our bus driver and tour guide were great.
Marco was a great guide.....
Avery_A, Feb 2023
Marco was a great guide.. the winery was beautiful and both towns were magical. I would recommend this tour
Elena_P, Feb 2023
It was nice, but It was too much 3 hours in Siena. Our guide was very nice, lunch very good. Too pitty it was a cold day
San gimignano is best view
Adam_K, Jan 2023
San gimignano was amazing had beautiful views. thanks Sandro and Francesca along with Martina our Siena guide of all the local info. . Rose wine tasting was great ordered some and oils. He’s Leonardo decáprios twin. Siena cathedral was stunning and nice to hear about as we have toured several throughout Italy on our trip. Only one with a severe engineer mistake they caught and saved many lives.
Great way to see the...
Ashley_K, Jan 2023
Great way to see the area! It’s a large buss tour but they did a good job giving free time and the walking tour in sienna was only a small group. The lunch felt a little like a time share for wine, but it checked the box of getting to a winery. Food was simple but not bad. The tour guide in sienna was a local a was a little eccentric but I enjoyed getting quick history and seeing the amazing church! It’s a long day and a few people in our group had a little trouble with the walking and duration. Bring snack and drink water. We also brought our toddler and they offered a car seat which was nice!
Well organised and...
Marina_V, Dec 2022
Well organised and worthy! The guide was very well informed of the area and friendly! Highly recommended!
The tour was really...
Federico_L, Dec 2022
The tour was really nice,intreasting, well explained and the tour guide Sandro was really top notch and super friendly. Really recomended!!
One of the best day trips from Florence !
Heather_B, Dec 2022
This was the best day trip everything was so beautiful and Constantino and Massimo were amazing as our guides. Everything was top notch and I seriously recommend it as a must do!
I recommend
Theresa_P, Dec 2022
Great tour guide, the lunch & wine tasting was exceptional. We spent a whole day out & we found it was a great value
Great scenery, unimpressive tour
Sandy_P, Dec 2022
Seeing San Gimignano and Siena was amazing but our guide literally "phoned it in". She never spoke to us(other than her spiel) unless we spoke to her, she didn't ask our names or where we were from-- completely different experience from the 4 Walks tour we had been on previously. And the owner at the Chianti tasting put the hard sell on us to buy. I don't think we'll take another viator tour anytime soon.
Enjoyable experience to see exceptional landmarks in a day tour around Florence
Jose_G, Nov 2022
Through ViATOR and considering that I will not have other way of transportation on my first visit to Florence, I wisely arranged a day tour with Marco from CAF Tour. Marco was a delight and very attentive to us. He explained relevant and interesting information in a clear and bilingual ability switching from English to Spanish. He made us to spend a memorable day in San Gimignano, Siena and the Wine Tour and lunch. The Winery host was very lively and made us comfortable. There was a vegetarian alternative to the local meat light lunch. Thanks for that!! I had a nice conversation with other customers as we share a communal long table. The coach driver Leo kept the vehicle very clean. Definitely, I would recommend this day tour with CAF Tours to anyone interested in explore outside and around Florence.
Great trip
Ranjan_T, Nov 2022
All of it. Great trip, fantastic guide and spectacular locales. Florence has a lot yo offer in terms of what you can do around and in the city
Tuscan adventure.
Bill_E, Nov 2022
Day was full of excitement and adventure. However the lunch was too rushed to be enjoyable. Maybe adding 30 Montes at he vineyard and reducing Siena by 30 minutes would have balanced things a little better
Perfect day trip
camilleluhrs, Nov 2022
Sandro was a great guide! The cities were beautiful! Ample time for photos and shopping. Definitely would recommend for a great day trip
Response from Host, Nov 2022
Good morning from Caf, we really appreciate your comment. Sandro will be glad that you had a great time with him. Hope to see you again in Florence. Thanks.