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Private Guided Tour: Explore Gothic City of Siena, Vineyards of Chianti and Medieval San Gimignano
4.8
22 Ratings
Siena
Embark on a private guided tour of the Gothic city of Siena, the vineyards of Chianti, and the medieval town of San Gimignano. Discover the beauty of Tuscany with expert guides and indulge in wine tasting experiences.
Embark on a private guided tour of the Gothic city of Siena, the vineyards of Chianti, and the medieval town of San Gimignano. Discover the beauty of Tuscany with expert guides and indulge in wine tasting experiences.
Duration:
8 hours
Cancellation:
24 hours
Highlights
-
Siena - Accompanied by a certified guide, explore the wonders of Siena!
Siena is renowned across Italy for its exceptional medieval architecture.
Upon arrival, delight in the city’s top landmarks, including the iconic shell-shaped Piazza del Campo and the 13th-century Siena Cathedral.
The historic streets of Siena are lined with numerous local…
- Siena - Accompanied by a certified guide, explore the wonders of Siena!
Siena is renowned across Italy for its exceptional medieval architecture.
Upon arrival, delight in the city’s top landmarks, including the iconic shell-shaped Piazza del Campo and the 13th-century Siena Cathedral.
The historic streets of Siena are lined with numerous local shops where visitors can savor local cuisine or purchase souvenirs!
- Chianti Road - A charming country road surrounded by the lush greenery of vineyards and olive trees - perfect for photo opportunities.
- Azienda Agricola Casa Emma - Optional Arrange a delightful lunch at a farm or winery with wine tasting (payable on-site) at Casa Emma or choose from several other options.
This choice will reduce time spent in the cities of Siena and/or San Gimignano and will exclude Monteriggioni.
- San Gimignano - A gem of medieval architecture, celebrated for its tower houses!
Enjoy free time at the final stop in the remarkable San Gimignano, offering a journey back to the Middle Ages.
- Chianti Road - Discover the Tuscan countryside as we drive through the Chianti hills. Don’t forget to stop for photos!
What's Included
- Bottled water
- Private guide in Siena
- Wi-Fi onboard (available upon request)
- Hotel pickup and drop-off in Florence
- Private guide in the wine cellar
- Bottled water
- Private guide in Siena
- Wi-Fi onboard (available upon request)
- Hotel pickup and drop-off in Florence
- Private guide in the wine cellar
What's Not Included
- Lunch
- Gratuities
- Museum/churches fee
- Lunch
- Gratuities
- Museum/churches fee
Additional Information
Experience a memorable day with your private group.
Join us for an extraordinary day exploring Siena with a professional city guide and the Chianti region, accompanied by one of our expert English-speaking drivers, who are native to Tuscany.
- During this 8-hour tour, discover the Gothic city of Siena, renowned for its iconic shell-shaped Piazza del…
Experience a memorable day with your private group.
Join us for an extraordinary day exploring Siena with a professional city guide and the Chianti region, accompanied by one of our expert English-speaking drivers, who are native to Tuscany.
-
During this 8-hour tour, discover the Gothic city of Siena, renowned for its iconic shell-shaped Piazza del Campo and stunning cathedral, all guided by a licensed tour guide!
For those interested in visiting the cathedral, there is a fee of €5 per person or €7 per person with priority access, payable directly to the guide. - In the afternoon, enjoy the chance to visit some of the most renowned vineyards or charming small family-run wineries, explore their cellars, and savor their exquisite wines and food.
- Conclude your day by exploring the enchanting medieval city of San Gimignano.
- A maximum of 7 people per booking
- Drivers are all extremely familiar with Tuscany and with the main destinations in Italy. They will always share information, curiosities and traditions about the area of the sightseeing and they are available at any needs.
Location
Siena
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
For a full refund, cancel at least 24 hours before the scheduled departure time.
Customer Ratings
4.8
(22 Ratings)
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Geneanddeanween
May 12, 2025
The only driver service I book as an expat in Italy for 2 decades! - I have lived in Italy for nearly 20 years and whenever I have friends or family visiting, I book Massimo as our driver. Some of my most memorable experiences in Italy have been out on an excursion with Chianti Drivers! This April, Massimo picked us up in Florence and took us to San Gimignano and Monteriggioni for time to explore on our own. Next, we headed to an exquisite winery for lunch and a cellar tour, before heading to Siena. Massimo is always exceedingly professional, punctual and polite. I cannot recommend this company enough!
Review provided by Tripadvisor
Anne_m
Mar 20, 2025
Highly Recommend! - Simone was wonderful. He was prompt, flexible and had a lot of interesting information to share. Our guide in Siena was very knowledgeable.
Review provided by Viator
Richard_h
May 25, 2024
I take the tour again - Great info provided by Massimo along the way. Viviana gave a tour of Siena.
Wine tasting at Emma’s winery was superb!
Review provided by Viator
Yobisss
Apr 12, 2024
Excellent tour. 10 stars!!! - We had an absolutely fantastic time. Two couples visiting from the United States. Simone, our driver, could not have been better. His knowledge was excellent. He took us on back roads and pointed out so many things we never would’ve gotten to see otherwise.
The visit to Casa Emma Winery was above par and the food was excellent. The wine was quite tasty and the winery was absolutely beautiful.
We highly recommend this company for a tour.
Review provided by Tripadvisor
G2180tbjoannaj
Mar 30, 2024
Unforgettable family Tuscany tour with Simone - Highly highly recommend booking this tour! My family and I were celebrating my mom's 50th birthday in Italy and we booked the private day tour with our driver Simone. Not only did he show us the beautiful hidden sights of Tuscany, but he was also a very kind and fun guy to spend the day with! Despite the rainy day, we had a wonderful time. Delicious wine tasting and lunch at Casa Emma. Thank you again Simone for the wonderful experience! :)
Review provided by Tripadvisor
C6276smtracyt
Oct 16, 2023
Awesome experience - Our trip with Marco was beyond what we expected from this private tour. He was knowledgeable, friendly and was a great guide, as we are first timers to Italy and unsure of the region we were visiting. The winery was great and loved visiting the other villages.
Review provided by Tripadvisor
Doug_b
Sep 6, 2023
Knowledgable guides and a comfortable ride - Simone was an excellent driver with great knowledge of the area. Our guide in Siena was very good as well, took us to a lot of hidden places in Siena. Lunch wine tasting was fantastic.
Review provided by Viator
Denise_g
Aug 13, 2023
See the sights and flavors of Tuscany - Our morning began with the prompt pick up of our driver Marco ( who’s English is very good)He told us about the beautiful areas we were driving through to Siena. Meeting our tour guide Claudia we walked and toured much of the city. The highlight was meeting her friend Emilio who allowed us to visit his studio as a master marble artist. The Palio race is just a few days ahead and the dirt track was laid. Claudia is so excited about the possibility of her Eagle neighborhood winning the race. It has been decades si c’è they have won. But each year gives a new opportunity.
The winery tour was brief, which was okay with us as we have been on such tours before. The tasting and lunch were outstanding. Roxanne filled us with information about the five wines we enjoyed and the lunch prepare by her mama - delicious. Given the chance to ship bottles home was a plus and we will be eager to see them arrive.
Our day was very good and we opted to ask Marco to skip the visit to Chianti. Our drive back to Florence was very picturesque.. it was a day filled with memories.
Review provided by Viator
Klam0719
Jul 3, 2023
Tuscan Day Trip - Our day in Tuscany was the highlight of our Florence trip. Cosomo was our driver and he was a pleasure to spend the day with. He drove us to Siena where we had a city tour with Vivianna. We were lucky enough to see the city set up for the Palio horse race which was two days away. The flags of the districts were on every corner and it added to the experience of learning what life inside Siena is like. Cosomo make reservations for us at Tenuta Casanova winery for a tour and lunch. The price is not included in the tour but I highly recommend including this in your day. The owner himself showed us around his winery and our wine tasting lunch was one of the best meals we’ve had in Italy. Last was an hour in San Gimignano, without a guide. I wished for more time here but we had a quick walk through and some amazing gelato at Gelateria Dondoli. I would love to go back and climb the towers one day. Overall a fantastic experience and I would highly recommend.
Review provided by Tripadvisor
Vbr0122
Mar 30, 2023
Fantastic. Loved Florence, Siena, San Geminiano and Chisnti - Very efficient Driver and Tour guide. Simone was very good. I would definitely recommend to my friends and family visiting Florence
Review provided by Tripadvisor
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