Private Tour of Chianti: Explore Siena, San Gimignano & Winery Visit by Minivan

Embark on a private tour of Chianti and explore the charming towns of Siena and San Gimignano. Visit a winery, taste local products, and customize your day to suit your interests.

Duration: 9 hours
Cancellation: 24 hours
Highlights
  • Piazzale Michelangelo - First stop is at Piazzale Michelangelo to take the most beautiful photos of florence
What's Included
  • Private transportation
  • Bottled water
  • In-vehicle air conditioning
What's Not Included
  • Lunch
  • Alcoholic beverages
Additional Information

Your bespoke day awaits. You’ll be in the capable hands of a dedicated driver who is committed to personalizing your experience based upon your preferences. Begin your day with a serene visit to Piazzale Michelangelo, home of some of Florence’s greatest photo opportunities, before journeying to Siena through the idyllic Tuscan countryside, surrounded by…

Location
Piazzale Michelangelo
Cancellation Policy

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

Customer Ratings
4.8
(74 Ratings)
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Debbie
Jun 21, 2025
Highly recommend! - Luigi was wonderful! We had 3 adults going for a specific visit to Siena and since we ended early, he suggested a vineyard on the way back - lovely! He was informative and helpful and we had a great day … so much so that when our train was cancelled 2 days later due to strike we reached out to see if he could be our driver to Venice and yes! I would highly recommend and use again if I am back in the area. Top notch service!
Review provided by Tripadvisor
Scenic719741
Jun 12, 2025
Amazing day trip with Luigi from Florence to Tuscany including Siena, San Gimignano, and wine tasting. - We spent an amazing day with Luigi in Tuscany. Luigi was incredibly knowledgable, a great driver, and such a nice guy. He took us to places we would never have found on our own. We visited Siena and San Gimignano which which are gorgeous towns and Luigi always brought us to the easiest access and most convenient locations. It was so easy with his help. We had an amazing wine tasting expreience at Arrigoni 1913 with delicious boutique wines and gorgeous views. It was just outside of San Gimignano. Overall it was an unforgettable day and Luigi made it happen for us. His Mercedes van was state of the art and brand new. 5 stars.
Review provided by Tripadvisor
Cynthia_m
Oct 23, 2024
Incredible Tuscany tour! - Great Service. Our guide Francesco was so helpful and flexible. Our family of six had a fantastic time. Thanks again Francesco!
Review provided by Viator
Steve_c
May 29, 2024
The only way to see the Tuscan countryside your way - Francesco was awesome. Almost as awesome as the Tuscan countryside. He was flexible and we customized our trip even the day of. In the morning, we had on the agenda to pay respects to my great uncle who gave the ultimate sacrifice at the American Florence Memorial. However, it was overrun by local politicians on Memorial Day. We cut short a little our Sienna and San Gimignano portions but absolutely took all of the local vineyard, wine, and food in on our lunch stop. We did a lot of tours / excursions from Rome to Sorrento via golf cart and boat, but this was at or near the top of the list for most family members when asked. We did hit the Memorial last in the afternoon. Note, you tour Sienna and San Gimignano yourself but they are small and easy to navigate. We had no problem given our compressed timeframe. We bought wine, olive oil, pesto, truffle salt, shoes, belts, soap, custom socks along the way. Luckily it all fit on our way home!
Review provided by Viator
Brian_w
Apr 7, 2024
Fantastic tour in Tuscany with Francesco - My wife and I had a wonderful time on this private Tuscan tour with our driver Francesco. Francesco was very warm and engaging and he did a great job driving in the comfortable minivan. He was knowledgeable on the area and history and never tired of answering my questions. The church in Siena was very beautiful and we enjoyed the large piazza. The lunch at the winery was great for both the food and the wine...we ended up purchasing wine from them. San Gimignano was very interesting and charming and the views over the Tuscan countryside were stunning. The drive back to Florence was also beautiful before we ended the day at Piazza Michelangelo with a great view over the city of Florence. This was an amazing day and we really appreciated seeing all the sights and enjoying our day with Francesco.
Review provided by Viator
John_g
Apr 4, 2024
Nothing like personal service in Tuscany - We had the best time with Francesco. He was a wonderful tour guide and driver for us. It was a rainy day and he greeted us at our condo door with umbrella's to get us to the tour van. We super enjoyed Sienna, Tenuta Guardastelle winery and San Gimignano. Francesco told us the secrets of each place we went and the best things to do or to try. You will have the best time and make the best memories on this tour.
Review provided by Viator
Keith_r
Oct 31, 2023
First class service. - Gino was fantastic. Went to great lengths to ensure he got us as close to the attractions as possible because of my wife's mobility issues. Could not recommend more highly. Thankyou Gino.
Review provided by Viator
425oreno
May 2, 2024
Beautiful Tuscany - Francesco is a very sweet and kind gentleman who really cared about our appreciation for Italy. We unfortunately, had rain all day, which really dampened our experience, however Francesco tried to accommodate and took us to an additional stop at a wine tasting cellar featuring hundreds of different wines and labels. Was super cool and made the day more special. The Mercedes mini van was nice and comfortable too.
Review provided by Tripadvisor
Becky_k
Dec 24, 2023
The driver was fantastic.... - The driver was fantastic. The car was clean and felt safe. The wine tour and lunch was amazing. I felt like it was a little misleading that there was no tour for Siena. That was very disappointing.
Review provided by Viator
Ioana
Aug 16, 2024
Nothing special, just transportation - The driver was not very friendly nor gave us infos. He was just a driver. In both cities he gave us a paper in the hand, one page with a map and few words about the places. This I could find much better on internet. No value for money. And in the end he repeated that his tour finishes at 17.00… we finished at 17.15 so 15 min later due to traffic, because we always returned on time to the Meeting points. So if you want to pay 650 eur for driving from Florenz to Sienna and San Giminiagno and back, its ok. But I guess that normal taxi or car rental is cheaper.
Review provided by Tripadvisor
From $764 (Per Group)
up to 6 guests
1 - Traveler
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).