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 - Renowned across Italy for its exceptional medieval architecture, Siena offers a delightful experience. Upon arrival, explore the remarkable local landmarks such as the iconic shell-shaped Piazza del Campo and the magnificent 13th-century Siena Cathedral. The historic streets of Siena are lined with charming shops where visitors can savor…
What's Included
  • Expert English-speaking driver
  • Bottled water
  • Onboard Wi-Fi (on request at reservation)
  • In-vehicle air conditioning
  • Private luxury car or minivan
  • Hotel pickup and drop-off in Florence
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 an experienced 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
4.8
(411 Ratings)
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Dana_s
Mar 26, 2026
Great experience.... - Great experience. Tailored trip To our needs. Clean and nice vehicle. Great service and kind driver.
Review provided by Viator
Mike_a
Mar 22, 2026
Fun day trip - Fun trip with the family, we especially enjoyed the winery visit with lunch. Our driver and guide was Samuel’s was informative and drove safely
Review provided by Viator
Chris_b
Mar 17, 2026
The guide was a pro! - It’s all about the guide. Marco was the absolute best we could have asked for. He had an extensive knowledge of the area and a great recommendation for a private wine tasting on a family winery/farm. Great day!
Review provided by Viator
Ian_m
Mar 12, 2026
Wonderful Day - Great local family owned vineyard experience. Great guide full of local knowledge and experience. Would recommend.
Review provided by Viator
W6sx8x2frj
Jan 1, 2026
Perfect! - Tour was perfect from beginning to end. Loved being able to customize on the spot. Do not skip lunch, we did Poggio Amorelli and loved every minute of it!
Review provided by Viator
Vincent_a
Dec 22, 2025
Simone is your guy! - Simone is hands down the best tour guide. Super friendly and warm and a wonderful storyteller! He went out of his way to bring us to the best spots for panoramic views, gave us great recommendations for dining in Florence and Rome. The tour that Simone put together is definitely one of the highlights of our very first visit to Italy. Thank you!
Review provided by Viator
Christopher_g
Nov 21, 2025
The personal touch from... - The personal touch from the tour was second to none. Our guide Marco was fun, informative, prompt and provided us with a one of a kind luncheon hosted by a working winery family. Amazing!
Review provided by Viator
Dean_s
Nov 15, 2025
This was an incredible... - This was an incredible experience getting outside of the city and going to the historic towns of Siena, San G, and Chianti. Our private tour guide, Simone has been guiding for 23 years, and was raised in Florence. His knowledge, and hospitality were 5 star! We love to book the private tours as we not only get to learn history, see beautiful towns and cities, but create wonderful memories. We ended up at a vineyard in Chianti and the day turned out perfect! Highly recommend Simone. Genuinely great person and passionate about sharing his knowledge and history of the area.
Review provided by Viator
Susan_s
Nov 4, 2025
Great private tour! - The tour with Samuele was wonderful and he is so knowledgeable about the Florence and Tuscany areas. He gave us a lot of information and facts about the areas we did not know about. It was a fantastic end to a long trip to Greece and other parts of Italy and it was nice to have the private tour with him in a very comfortable van.. He is a great driver too!
Review provided by Viator
Kennedy_p
Dec 2, 2025
Good tour of tuscan countryside - Massimo was an excellent driver and very kind. The scenery was beautiful and crowds were minimal. Only docking this experience 1 star because the day felt very long, and there wasn't much to do besides walk around with no guide. The winery was not worth the $165 if you're not a red wine drinker.
Review provided by Viator
From $812 (Per Vehicle)
up to 15 guests
1 - Traveler
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).