Tuscany Private Tour: Chianti, Siena & San Gimignano

Embark on a private full-day tour from Florence to Siena, San Gimignano, and Chianti. Explore medieval cities, taste Chianti Classico wine, and indulge in traditional Tuscan cuisine.

Duration: 9 hours
Cancellation: 24 hours
Highlights
  • Siena - Siena is a highly popular and frequently visited destination in Tuscany, celebrated across Italy for its remarkable medieval architecture. Upon arrival, delve into its rich history and art by visiting its notable landmarks, such as the renowned seashell-shaped Piazza del Campo and the magnificent Siena Cathedral. The historic streets of…
What's Included
  • Unlimited cold mineral water
  • English-speaking licensed driver
  • On-Board WiFi
  • Private transportation by Mercedes-Benz MiniVan, Air-Conditioned
  • Free time in Siena and San Gimignano
  • Pick-up and drop-off at your selected hotel/location (in Downtown Florence)
Additional Information

• EXCLUSIVE EXPERIENCE FOR YOUR GROUP •
Embark on an enchanting journey to a distinctive part of Tuscany with a private day-trip from Florence. Accompanied by a knowledgeable local driver/guide, delve into the celebrated Chianti wine region and visit the charming cities of Siena and San Gimignano. Explore historic sites such as Siena’s Piazza del…

Location
Siena
Cancellation Policy

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

Customer Ratings
5.0
(220 Ratings)
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Ssendro
Jul 30, 2025
Absolute Dream Day in Tuscany - We just got back from our day trip with Alessandro and wanted to write a review right away. It was a 10 out of 10 perfect day. We went as a family with 2 teens and a 10 year old, and we all had the best day in Sienna, San Gimignano and especially at our winery lunch. Alessandro picked us up directly at our accommodation in his comfortable and spotlessly clean Mercedes van. He was so warm, friendly and very knowledgeable about the region of Tuscany. At each stop, his suggestions were spot on for what our family would enjoy. He selected a small, organic winery with wine and olive oil tasting for our lunch in the most beautiful setting. It was like a dream! We made the most incredible family memories today and are so grateful to Alessandro for curating such a lovely experience. Don’t hesitate—book this experience now.
Review provided by Tripadvisor
B8284neamandac
Jul 30, 2025
Picturesque views and amazing locations with a world class guide! - Amazing isn’t a strong enough word to describe this tour. Alessandro was a wonderful tour guide. Explains everything and so accommodating. Would highly recommend this tour to anyone who wants to get to see the beautiful highlights of Tuscany! The whole family, including teens, loved every minute of this tour.
Review provided by Tripadvisor
Elizabeths22779
Jul 24, 2025
Amazing Day Tour of Tuscany with Alessandro - We had an amazing day touring Tuscany with Alessandro! He arrived on time, is very friendly, knowledgeable and so informative throughout the day. He brought us to Siena where there is the most beautiful church and to San Gimignano which we really loved and had amazing gelato! We had an amazing lunch at a winery he chose for us that had gorgeous views, delicious wine & food and was family friendly. Perfect for our family of 6. We had an amazing day and I would recommend anyone take a tour with Alessandro!
Review provided by Tripadvisor
Adria_b
Jul 14, 2025
This tour was a highlight... - This tour was a highlight of our trip. Alessandro was fantastic - very friendly and knowledgable. We had enough time to explore each location. We also chose the option of having lunch at a winery and loved it - we are still talking about that meal. We would definitely book another tour with Alessandro again, and we have already recommended this tour to other folks. Thank you!
Review provided by Viator
Bengc6870th
Jul 11, 2025
Unforgettable Tuscan experience with world-class guide! - My wife and I booked with Alessandro for this trip during our honeymoon and it was one of the best days we had of the entire trip! He conveniently picked us up from our hotel in Florence and provided history and background information on the city as we drove to Siena. Being from Canada, we appreciated Alessandro’s PERFECT English, and we had great conversations the entire day while learning about these wonderful Tuscan areas. We were provided with a comfortable ride, cold bottled water and endless suggestions on where to eat, what to do and even recommendations for Florence and other places in Italy we planned to visit that weren’t part of the tour. We had plenty of time to spend in both Siena and San Gimignano—which are UNMISSABLE cities in such a beautiful region of Tuscany. Even though we are not catholic, we were astounded by the beauty of the Cathedral in Siena. San Gimignano was incredibly interesting and a fun place to walk around in—Alessandro suggested a gelateria there and it may have been the best we’ve had! Alessandro also ensured that we made time to visit some sites we had suggested that weren’t necessarily part of the tour itself. He made our time in each city customizable, and we appreciated that. Lunch at the organic vineyard was outstanding—truly a highlight of the tour…you won’t go hungry! Even though we saw so much in one day, the tour never felt rushed. We so much enjoyed Alessandro’s charisma, knowledge and professionalism. He is truly one of a kind and so is this tour. We would recommend Alessandro and this tour to anyone visiting Tuscany—especially for the first time.
Review provided by Tripadvisor
Eric
Jun 25, 2025
Amazing - Superb day trip from Florence. Unique Tuscany private tours took us from the front door of our hotel to tour the Tuscan region. We saw amazing towns. Tasted amazing wine. Heard amazing stories. Learned amazing things. We are seasoned travelers and unique Tuscany private tours is top notch. Highly recommended.
Review provided by Tripadvisor
M0nd0nnak
Jun 13, 2025
Wonderful day from start to finish! - Alessandro of Unique Tuscany was everything you could ask for in a driver and guide. He’s fantastic!! We took a day trip to Siena and San Gimignano and stopped for a relaxing lunch and wine tasting at a beautiful winery he chose for us which with amazing views. He was on time, his van was comfortable and he had cold bottled water which was very nice since it was very hot out. He made sure we saw everything we wanted to in the time we had yet flexible with time too. He also had great suggestions for during the trip and also back in Florence. I would definitely book Unique Tuscany again without hesitation.
Review provided by Tripadvisor
Trout2423
Jun 10, 2025
Relaxing, efficient and beautiful. - Alessandro with Tuscany Day Trips did a great job for us. Sharing the history of the places we visited, keeping our steps to a minimum and finding a great unique winery for lunch. We highly recommend him and Tuscany Day Trips.
Review provided by Tripadvisor
Deshana
Jun 7, 2025
Great tour! - Alessandro was amazing. He did a wonderful job explaining the culture and the regions. We did a wine tasting at a wonderful family vineyard. I would recommend him 100%!!!
Review provided by Tripadvisor
Nollnicole
May 28, 2025
Private Tuscany tour - We had the absolute best day with Alex in our tour of Tuscany. He was so knowledgeable and made the day extra special. We were able to walk around Siena which was stunning and then spent time at his special small farm winery where we had the best wine tasting and lunch. After that we walked about beautiful San Gimignano which felt like a fairy tale village. Our day was everything I hoped it would be. Highly recommend for anyone looking for a private tour of this beautiful country side.
Review provided by Tripadvisor
From $126
up to 7 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).