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
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
(371 Ratings)
5 stars
4 stars
3 stars
2 stars
1 star
Danica_v
May 21, 2025
Bellissimo - Absolutely beautiful! We booked this tour for 7 and did the wine tour! First and foremost, Massimo, our driver/ tour guide was amazing. He was a great driver, informative, patient, and a great photographer! We visited all stops listed and just blown away by how beautiful each town was. The winery is a must! A perfect tour from start to finish. Highly recommend booking this tour! You will not be disappointed!!! Grazie millie Massimo and Chianti Drivers!!
Review provided by Viator
Seans995
May 21, 2025
5 Stars - Marco was great. Very knowledgeable about Siena and San Gimignano. The lunch at the winery was quintessential Tuscany. I would recommend to anyone who wants to spend a day out of Florence and in the countryside.
Review provided by Tripadvisor
Lourdesh844
May 20, 2025
San Gimignano, Siena and Chianti day trip - Definitely should be included in your Florence trip! Loved the Medieval town of San Gimignano, Sienna and the wine tasting paired with lunch was the icing on the cake! Our Chanti driver provided us with the history lesson on our way to each town and Chianti region. Gratzi!
Review provided by Tripadvisor
Jodi_p
May 19, 2025
Excellent experience! - We loved our tour of Tuscany! Sam was an excellent driver! He told us about the area & prepared for what we were seeing in each town. We highly recommend this tour & Sam as a driver!
Review provided by Viator
Nicolle_p
May 18, 2025
Incredible experience! - Amazing experience in the Tuscany region! My mom and I had plenty of time to explore each city and our private driver, Marco, gave us several tips and excellent information about each town/winery.this tour was the highlight of my 10 day trip in Italy! Highly recommend!
Review provided by Viator
Jairie
May 14, 2025
Awesome postcard Tuscany day trip. - Fantastic day with our driver and guide Massimo. He is a very knowledgable about the area, picked us up promptly in the morning and provided us with a tour of the areas in Tuscany, pointing out great scenic backgrounds for pictures a pitstop at Michelangelo Square and ended the day at a nice Chianti Vineyard. He was friendly and accommodating and we appreciated his knowledge and direction. The passenger van was very comfortable and nicely air-conditioned.
Review provided by Tripadvisor
Lori_k
May 11, 2025
Mario was the best - Mario was wonderful. He was helpful and informative and got us a reservation that day at a winery with both my husband and I being vegetarian. The wine tasting was delicious and couldn't have been happier with the service and his kindness. Van was clean and new and Mario was a great driver.
Review provided by Viator
Terry_j
May 6, 2025
Driver and guide was very... - Driver and guide was very knowledgeable from the very start to the last stop. He had great insight on all the stop. He was kind, courteous and a wonderful gentleman.
Review provided by Viator
Pioneer34137131332
Apr 17, 2025
Quiet day in Tuscany - Our driver was exceptionally knowledgeable and friendly. Took us to historic towns in Tuscany as well as showing us the beautiful countryside. Very accommodating.
Review provided by Tripadvisor
Jaya_l
Apr 28, 2025
Disappointed with this tour experience! - We had paid and understood that we were hoping to visit three towns , Sienna , San Gimignano and Chianti . However we only ended up seeing two cities . We did not even see Chianti ! We did not get an opportunity to see even drive close to a winery . Th latter part of the tour was not explained Pontus or we did but know what we were doing or seeing . No explanation!! We are sorry and disappointed with this tour experience , considering the money we spent on this tour !
Review provided by Viator
From $809 (Per Vehicle)
up to 7 guests
1 - Traveler
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).