Private Guided Tour: Explore Gothic City of Siena, Vineyards of Chianti and Medieval San Gimignano
4.7
19 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.
Duration: 8 hours
Cancellation: 1 day learn more
Highlights
  • Siena - Followed by an authorized guide you will visit Siena!\n\nSiena is known throughout Italy for the quality of its medieval architecture. \n\nUpon arrival, enjoy the best local monuments such as the famous Conch-shaped Piazza del Campo and the 13th-century Siena Cathedral.\n\nMany local shops fill the historic streets of Siena that will allow you to taste local food or buy some gifts!\n\n- Chianti Road - enchanting country road surronded by greenery of vineyards and olive trees - stop for pictures/shooting\n- Tenuta Casanova - As an OPTION We can organize a Lunch in a Farm where you can taste wines and organic local products. (to be paid on the spot) \n\nThis option will reduce the time in the cities of Siena and San Gimignano and exclude Monteriggioni.\n\n- San Gimignano - A pearl of medieval architecture famous for its tower houses!\n\nFree time for the last stop in the incredible San Gimignano, a dive into the Middle Ages.\n\n- Chianti Road - We explore the country of Tuscany, we will drive through the chianti hills. Stop for picture!!!!
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
What's Not Included
  • Lunch
  • Gratuities
  • Museum/churches fee
Additional Information

Exclusive experience for your private group.

Join us for a memorable day touring Siena with a professional city guide and the Chianti region escorted by one of our proficient English speaking drivers who were born and raised in Tuscany.
-During this 8hr journey, you will discover the Gothic city of Siena with its renowned seashell-shaped Piazza del Campo and the magnificent cathedral, accompanied by a licensed TOUR GUIDE at each step!
Should you wish to visit the cathedral, you can pay an additional euro 5 per person or euro 7pp for priority to the guide directly.
-In the latter part of the day, you’ll have the chance to visit some of the most prestigious vineyards, or lesser-known family-owned enterprises, explore their wine cellars, and taste their superb wines and food.
-Finally, uncover the beautiful 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.

Customer Ratings
4.7
(19 Ratings)
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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
Brooks_b
Mar 3, 2023
Teens and elementary children cold March day - Massimo was an excellent, very friendly driver who enjoyed telling us about beautiful Florence and Tuscany. There were few crowds on this cold March day. I wish I would have brought an extra layer to enjoy the cold gelato more. It was nice to have a guide in Siena with our boys ages 15-8. But if it would have been just my wife and I, the guide book or audio tour would have been enough.
Review provided by Viator
Vanessa_b
Nov 29, 2022
Best way to experience Siena, San Gimignano and Chianti in one day - Absolutely outstanding experience. Can’t recommend this tour enough. Simone our driver made the day an incredible experience. Can’t wait to do it again. Loved every minute
Review provided by Viator
Analy_z
Nov 13, 2022
Great Experience! - Miguel was our driver and he is the nicest person. He made our day so fun and so memorable. He went out of his way to make sure we had an amazing experience. We had the best wine tasting experience and beautiful views in Chianti!
Review provided by Viator
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May 2024
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