Siena San Gimignano Chianti Pisa and Lunch with Wine Tasting

Firenze, Italy

From $64.60

Select Date and Travelers

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


Visit the highlights of Tuscany in a single day on a tour from Florence. Explore Pisa, Chianti, San Gimignano, and enjoy a guided walking tour and entrance ticket to the cathedral Siena. Then visit a family-run Chianti winery for a traditional Italian lunch accompanied by a Chianti tasting. 
  • Walking tour of Siena with a local guide
  • Entrance to the Siena Cathedral (if option selected)
  • Free time in Pisa and San Gimignano
  • Lunch at a Chianti winery with wine

What's Included

  • Transport by GT air conditioned bus with WIFI on board
  • Licensed Tour Escort
  • Siena Guided Visit with Professional Local Guide
  • Enjoy a delicious Tuscan Lunch with drinks 
  • Earphones during Siena Guided Visit
  • April - October monolingual Visit in Siena
  • If Option selected: Guided visit inside Siena Cathedral with entrance fee
  • Semi indipendent Option includes: Transport-Tour escort on board-Typical Lunch
  • From April 1st 2023: Lunch in a characteristic Restaurant located along the famous "Via Francigena".
  • Semi independent Option does NOT include: Siena Guided Visit and Cathedral admission

Meeting And Pickup

Meeting point

  • Piazzale Montelungo
    Piazzale Montelungo, Firenze FI, Italy

    At 07:15 am, at Piazzale Montelungo (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

07:30 AM

End point

This activity ends back at the meeting point.

What To Expect

Meet your tour guide and group at the departure point and climb into the comfortable tour bus bound for Siena. During the journey, enjoy views of Chianti vineyards. 

Arrive in Siena in the morning, as the town is just waking up, to meet your local Siena guide for a walking tour of the hilltop town. Walk through the squares and alleyways, passing the Piazza del Campo and the world's oldest bank. Explore the Siena Cathedral (entrance fee included). Then, enjoy free time to wander around Siena before departing for lunch. 

At the family-run winery, sit down for a traditional Tuscan lunch accompanied by wine. 

Continue to the UNESCO World Heritage Site of San Gimignano, famous for its still-intact medieval town plan. Spend your free time discovering the town's treasures on your own before departing for Pisa. 

In Pisa, disembark at the Field of Miracles (Piazza dei Miracoli): a green field populated by buildings exemplary of Romanesque architecture. See the Duomo, the Tower, the Baptistery, and the famous Leaning Tower of Pisa.

After your time in Pisa, board your bus for the trip back to Florence, where you are dropped off at your departure point.

Piazza del Campo

Upon arrival in Siena our local guide will take you on a guided walking tour along the small medieval streets and squares, passing passing the oldest bank in the world, and the Piazza del Campo - site of the famous 600-year-old Palio horse-race, to the spectacular Cathedral

1 hour Admission Ticket Free

Duomo di Siena

The spectacular Cathedral of the 12th century, of which we can admire the magnificent architecture and the splendor of the polychrome marbles

30 minutesAdmission Ticket Included

Additional Info

  • Confirmation will be received at time of booking
  • Not wheelchair accessible
  • Comfortable shoes suggested
  • Appropriate clothing is recommended to visit places of worship
  • Please advise any specific dietary requirements at time of booking
  • 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.
  • Travelers should have a moderate physical fitness level
  • Starting from April 1st 2023 the typical Lunch will be served in a characteristic Restaurant which is located along the ancient medieval road that led pilgrims to Rome crossing Tuscany, the famous "Via Francigena".
  • 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.

Traveler Photos

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Traveler Tips

Bus could not get close to the attractions so it required lots of uphill and uneven walking.
Due to alot of waliking, i will not recommend this tour in the summer when it is hotter.
The hole city, and the Domus specially worth a more extended visit.
159 reviews
Total review count and overall rating based on Viator and Tripadvisor reviews
Reviews by Viator travelers.
Showing 1-10 of 159 reviews
Best of Italy!!!
Sandra_G, Mar 2023
Sandro was an excellent tour guide. He showed us the most exquisite sites of our tour. He was thorough and really gave us an appreciation for the cities we saw. Nothing but beauty and tranquility was what we were exposed to. Loved every minute!!! Thank you for a memorable experience.
Picturesque and magical
TriciaVara, Feb 2023
We had the best time! Sandro was enthusiastic which added to the experience. He shared a lot of details about the areas we visited. The winery was awesome and they provided an excellent tasty lunch paired with excellent wine. Personally, I loved the wine so much that I overbought some to be shipped back home. Totally looking forward to that when I get back. San Gimignano is one of the most picturesque places to visit. It was a great way to spend my 50th birthday.
Fully recommended
Luis_S, Jan 2023
Great experience. Great guide. Everything was fine. All the cities visited are a must see. The visit and lunch to the winery is very interesting.
Great tour!
Melanie_M, Nov 2022
Great tour. The driver and guide were very efficient and we stayed on time. Just enough time in each place , not too long which was fine !
Just OK
mjpulvermacher, Nov 2022
We were very exited for the trip but it was a little disappointing. It all seemed very rushed. We had no time to climb the Tower of Pisa because we had to ge Thackeray to the bus. Our winery lunch was good. We stopped at Siena but when we got to San Gimigano we were to see the sunset but the sun was set before we arrived. I feel that it was too many places and not enough time to enjoy any of them. Also did not like that it was mixed English and Spanish because it was a lot for the guide to explain
Best day ever!
LaxMom, Oct 2022
Sandro was an exceptional tour guide. He was helpful, funny, and informative. Siena was unbelievably beautiful. We did the tour of the city with a local guide. Which was great but I would have liked more time to wander. San Gimignano was just as beautiful. The view from the city of the countryside was unbelievably beautiful. The lunch was excellent, the wine so-so. Pisa was beautiful. An excellent experience that I will never forget.
Enjoyable, and highly recommendable.
John_R, Sep 2022
Enjoyable trip, but too rushed. Considering how much it was covering; understandable. All locations we visited are beautiful, and deserve a longer 2nd visit. Due to the distance between locations, you spend the majority of your time on the bus. Complaints: There was confusion at the meeting place. The tour guide was late, and no backup. The tour guide was professional, knowledgeable, and efficient. However, I found her some what aloof, and appeared to have little interest in interacting with the clients. Also, there should be some commentary, regarding the areas we drove through. Historical, agricultural, population, etc. The only commentary made was regarding the places we were visiting. The bus driver was pleasant, and efficient, and was trying to meet time schedules. But I feel he drove a little recklessly, on the mountain part of the trip.
Araks_D, Aug 2022
It was the best tour I have ever had the tour guide Maria Louis was wonderful explaining all the Hugo and the details very officiants and polite couple of guests gave her hard time but she handled very professionally
Not happy!
evapner, Jul 2022
The sites are amazing but very little description or talking from my guide. She spoke different languages and I picked english. When you have a multi-lingual guide how much can she really describe or discuss. Her English was broken. Need to do better guys! She even told me in some places I can’t talk like in Siena but the other guides didn’t do much talking either. Very disappointing for the amount I paid I wanted to learn about
This is a quick hit tour...
Hardi_A, Jul 2022
This is a quick hit tour to explore 3 places and with a vineyard luncheon . There is not a lot of time to explore Siene and San Gigimano. But gives a flavour , if u have more days later, u can go back and explore more later
Good trip
Marwa_B, Jul 2022
Our Guide Sebastian was amazing ! Very nice, easy going, funny he went on our pace and suggested to help us several times. The driver, the trip and all the program was very nice ! The only thing that I have not really liked is the food the proportions are very small and when it’s a vegetarian dish, there is nothing special about it !
A perfect sample of Tuscany
Craig_F, Jul 2022
Our tour guide, Maria Luisa, was excellent. She was very patient with me attempting to practice my Italian on her. The travel didn’t seem too long between destinations. Our tour guide sensed when the group needed entertaining and when they needed to relax in between our destinations. The vineyard guide was exceptionally good and very humouress. The lunch was tastey. We could have had more time in sienna and less in Pisa but that is just personal choice. An excellent tour smd very good value for money.
The guide was lovely and...
Helen_B, Jul 2022
The guide was lovely and friendly. Lunch in the winery was beautiful as were all the locations we visited. Picturesque and pretty.
andrew_b, Jun 2022
Was great. THank you. The company that took care of did a great job. The tour was fantastic. Thank you
Pisa, Tuscany, Sienna and San Magnano whole day tour
Franco_F, Jun 2022
Whole day tour of Florence, Pisa, Sienna, Tuscany wine and San Magnano are all beautiful to see while in Italy
Bad experience and waste of money
KARIN_M, May 2022
The guide on our bus was not friendly and we were always rushed. Hardly had time to take pictures as our guide was always rushing and it was hard to keep up. The guide gave us all the information on the bus so when we reached our destination we had no idea what she was talking about. If we had a much more knowledgeable guide we would have had a better experience on this tour. The guide we had in Siena was knowledgeable but we were also rushed.
Had a great time at the...
Andreas_K, Apr 2022
Had a great time at the winery, learned a lot too. Great punctuality, always on time. Martha very helpful, Paul the guide was amazing.
Could be much better
Catalin_S, Aug 2021
The tour wasn't bad in theory. But the guide wasn't too entertaining and haven't felt any connection during the tour.
Nice tour!
Keri_C, Jan 2020
The tour guide was great! The tours of the 3 towns were very nice. The lunch and wine tasting was disappointing.
Response from Host, Feb 2020
Dear kericampbell123, many thanks for having booked one of our activities and having shared your experience with us and our common readers. We are really happy to see that you appreciated our Highlights of Tuscany: Siena, San Gimignano, Chianti, Pisa & Lunch in a Winery, the best choice if you have not so much time at your disposal and you want to visit the highlights of our beautiful Italian Region. We hope to meet you again in the future to show you other wonders of our magical Country! Best regards
janetd3t, Jan 2020
Our tour guide was wonderful and very knowledgeable. We we’re disappointed that we didn’t go to Chianti or have lunch in a typical winery. Our lunch was in a restaurant. We loved sienna and San Gimignano bit did not care for Pisa If I had the opportunity to do it again I would choose a trip to the winery instead