Private Tuscany Tour: Discover Siena, San Gimignano, and Chianti Wine Region from Florence

Embark on a private Tuscany tour from Florence and uncover the hidden gems of Siena, San Gimignano, and the Chianti wine region. Immerse yourself in art, culture, and medieval history while indulging in a wine tasting experience.

Duration: 8 hours
Cancellation: 24 hours
Highlights
  • Siena - Siena is known throughout Italy for the quality of its medieval architecture.
    Upon arrival, enjoy the best local monuments such as the famous Conch-shaped Piazza del Campo and the outstanding 13th-century Siena Cathedral.
    Many local shops fill the historic streets of Siena that will allow you to taste or taste local food or buy some…
What's Included
  • Expert English-speaking driver
  • Extensive knowledge of Tuscany and main Italian destinations with anecdotes and curiosities
  • Complimentary bottled water
  • Onboard Wi-Fi available (request at booking)
  • Comfortable in-vehicle air conditioning
  • Convenient hotel pickup and drop-off in Florence
  • Travel in style with a private luxury minivan
What's Not Included
  • Full lunch + wine tasting at winery (to be paid on spot) from 50/70 euros per adult
  • mance
  • Licensed Guide in Siena
Additional Information

Experience for Your Private Party
Embark on an 8-hour private tour to explore the art, culture, and medieval history of Italy. Enjoy a private day trip from Florence to discover the wonders of Tuscany. With a knowledgeable English-speaking private driver, journey through the famous Chianti wine region to visit the towns of Siena, the Monteriggioni…

Location
Siena
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.9
(401 Ratings)
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Tasnim_k
Oct 25, 2025
Sienna & Gimignano tour - Massimo was absolutely fantastic he went out of his way to shoe us part of Florence that was not included. He never rushed us, we took our time to see San Gimignanomi and Sienna and the wine tour. Definitely recommend Massimo and Viator. So far we have enjoyed all the services provided through Viator Tours. Thank you Massimo for an incredible experience.
Review provided by Viator
Jeanlouise_d
Oct 14, 2025
My husband and I had an... - My husband and I had an amazing experience with our driver, Marco. He was very flexible and knowledgeable about the history of the area. He supplied us with options and tailored our day around what we wanted to do and see. I highly recommend the lunch in the vineyard with the wine tasting! We had a great day!
Review provided by Viator
Doug_b
Oct 9, 2025
What a great day!... - What a great day! Visiting Siena, driving through the beautiful Tuscan countryside, and eating at a winery were the perfect activities after a few days in Florence.
Review provided by Viator
34bethz
Oct 5, 2025
Magical Day in Tuscany - It was a perfect day! Our driver, Marco, was professional, friendly, and very knowledgeable about the area. The countryside was breathtaking and we went to a farm/winery for lunch and tasting — it was stunning! It felt like we were living in a movie. We visited Siena and San Gimignano — both were charming little towns. The entire experience was magical!
Review provided by Tripadvisor
Susiew642015
Oct 2, 2025
Amazing - Our driver, Samuela, was amazing. Prompt pickup, helpful and very informative and kind. Loved the tour and would highly recommend.
Review provided by Tripadvisor
Laura_s
Oct 1, 2025
Must do! - Marco was an amazing driver and so knowable. We had a great time. He took us to a cute winery for a tasting lunch and to two smaller walled cities and sienna.
Review provided by Viator
Paul_s
Sep 29, 2025
Tuscan adventure day - We stopped at Montaregioni, Sienna, a beautiful winery in the Tuscan countryside for lunch and wine tasting and finished at San Gimignano. It was a perfect day and a perfect pace. Carlo was very knowledgeable and amenable to all our wishes. Great day.
Review provided by Viator
Jennifer_c
Sep 24, 2025
Great trip to the Countryside - David was great- good insights on the town and very friendly! We loved the lunch at family vineyard in Chianti. Amazing. Perfect way to explore the countryside of San Gimignano and Siena. Highly recommend
Review provided by Viator
Kevin_m
Sep 23, 2025
Fantastic day in Chianti - Our driver Marco was fantastic. He was engaging and knowledgeable, having been born and raised in Siena. The vineyard we stopped at for lunch was a great family run winery. We got to meet the owner and had a knowledgeable guide give us a tour there. The view during lunch of the hills and valley around the vineyard was stunning. Marco offered an option to replace our visit to San Gimignano with stops at two small villages with a scenic drive through the mountains. We found this a nice chill alternative and authentic Italian experience after walking among so many tourists in Siena and Florence. We would do this tour again in a heartbeat.
Review provided by Viator
Daniel_k
Sep 29, 2025
Trip to sienna and winery tour - The driver, Samuela, was very knowledgeable, friendly, courteous, helpful, and took us to an excellent winery tour and lunch. However, Samuela is not a tour guide and could not accompany us and guide us through the sites. We expected a tour guide, not a self-guided tour. Therefore, I think a refund is in order as this tour is completely misrepresented.
Review provided by Viator
From $798 (Per Vehicle)
up to 7 guests
1 - Traveler
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).