Private Tour: Siena, San Gimignano And Chianti Day Trip From Florence

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Tour Information

Key Details

  • Mobile Voucher Accepted
  • Hotel pickup Available
  • Free Cancellation
  • Duration: 9 Hrs
  • Language:
  • Departure Time :
    9:30 AM
  • Departure Details :
    Traveler pickup is offered
    Pick up from all hotels or apartments in Florence downtown
  • Return Details :
    Your centrally located Florence hotel
  • Cancellation Policy :
    For a full refund, cancel at least 24 hours in advance of the start date of the experience. Tours booked using discount coupon codes will be non refundable.


Explore the art, culture and medieval history of Italy on this private 8/9-hour Siena, San Gimignano and Chianti countryside tour from Florence. Book the experience for your private group (up to eight people max), and visit the UNESCOlisted city of Siena. Discover top attractions such as the Piazza del Campo and the 13th-century Siena Cathedral. Stroll along the bustling Via di Citt then head into the Chianti countryside, where fertile hillsides line the route. Visit the fortress of Monteriggioni, explore the wonderful medieval city of  San Gimignano.
Enjoy personal attention from your driver/guide.

  • Our drivers are all extremely familiar with Tuscany and with the main destinations. They will always share historical information, curiosities and traditions about the area of the sightseeing and they are available at any needs.


  • Ideal choice for families
  • Flexibility to customize your itinerary to your own preferences
  • Free hotel pickup and drop-off included

Know More about this tour

Hop into your luxury minivan in the morning at your hotel in Florence, then relax on the 1-hour journey to the UNESCO World Heritagelisted city of Siena. Widely considered among Tuscanys prettiest settlements, Siena is known across Italy for the quality of its medieval architecture.

On arrival, take in top local landmarks such as the famous shell-shaped Piazza del Campo and the 13th-century Siena Cathedral. With your private guide to lead the way, explore the Via di Citt and Via Banchi di Sopra, where historic buildings and bustling shops line the walkways.

During your privatetour, you'll visit the medieval fortress of Monteriggioni nestled deep in the Chianti countryside and mentioned by Dante in The Divine Comedy on route to the beautiful old town of San Gimignano. Here, admire the soaring towers which dominate the skyline.

Stroll along the narrow streets and of the town and soak up the magical atmosphere. Along the way, gain insight into the regions rich medieval heritage. When your time in San Gimignano ends, return in comfort to Florence to conclude your tour.


Hotel pickup and drop-off in Florence

Private luxury minivan

Bottled water

Onboard Wi-Fi (on request at reservation)

Our 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.

Spanish-, Portuguese- or French-speaking driver upon request




Guide city tour (you will find the complete tour with private guide in Siena on viator with this code 23322P50)

Wine tasting

Additional Info

Confirmation will be received at time of booking

Infant seats available

A maximum of eight people per booking

Wheelchair accessible

Stroller accessible

Most travelers can participate

This is a private tour/activity. Only your group will participate

Traveler Reviews

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  • 09-Dec-2019

    Our trip with Simone was excellent. I booked a last minute tour to Siena, San Gimignano and Chianti and was amazed at how everything went without a hitch. Simone was very nice and knowledgeable. He took us to great restaurant for lunch where we had a wonderful time. Opted for a wine tasting stop and it was also awesome. Highly recommended. We were party of 8 and tour was on Dec 04’19.

  • 08-Oct-2019

    This tour was wonderful! We went to Siena, a winery for lunch and tasting and then San Gimignano. He even took us by Piazza Michelangelo on the way back to our airbnb and got some great photos for us. Gino went above and beyond to make sure our trip was perfect. I would definitely recommend this tour!

  • 01-Oct-2019

    Alex provided a whirlwind tour of the area. He was very happy to tailor the tour for our needs, was very knowledgeable and extremely accommodating. Thank you

  • 30-Sep-2019

    We had Alex as our guide and he was wonderful! He was very personable and knowledgeable, especially about wine. He took us to a farm where we had a delicious lunch and tour of their winery. It was the best day of my 14 day vacation in Italy!

  • 16-Sep-2019

    Alex was very informative, professional and patient. He gave a great tour of the vineyards and explained the wine making process to the point of stopping and showing us the grapes.

  • 21-Aug-2019

    My wife and I had a great time with our private tour guide Alessandro. It was our first time in Tuscany and did not want to go through the hassle of renting a car and navigating through the cities.

    Alessandro went out of his way to give us the history and explanations of everywhere we visited along with the history of the Tuscany region.

    The tour was flexible and catered to our wishes with Alessandro going out of the way to show us specific things we wanted to see.

    Highly recommended.

  • 13-Aug-2019

    This was a great private day trip. Private is the way to go. We were able to customize the itinerary a bit and Alex/Alessandro was very knowledgeable and helpful This was a highlight of our trip!!!! We really liked walking through the small villages.

  • 03-Jul-2019

    The private tour in our limo service with our driver Alex was excellent. He was on time to pick us at the hotel and is a very corteous, friendly and well prepared driver. Although he is not a tour guide, he provided us with useful and enough information about the placed we were going to visit and along the way. He managed to schedule proper times for visiting the towns of Siena and San Giminiagno as well as to book a wonderful lunch at a local farm were we tasted good Chianti wines and food prepared by the owners. The only down side was the server at lunch, which tried to do a good job but prevented us from enjoying a peaceful time from all the information she gave about everything. This of course is not a problem of the company which provided our private tour but more of the farm staff. Other than that the tour went flawless, we enjoyed a lot the experience and we returned on time to our hotel feeling refreshed and not tired because of the one to one service and the comfortable ride. We would highly recommend the tour to friends and family.

  • 01-Aug-2018

    Best tour of the entire trip. Had no idea what to expect out in the country. Siena was a beautiful old town with a round city square. A stop by Monteriggioni for lunch was fun. The drive through Tuscany was filled with beauty. Highly recommend this private tour so you can spend the time you want along the way!

  • 22-Apr-2018

    Our driver Alessandro was outstanding!! He was so knowledgeable about the region and especially the wine. In addition to our visits Siena and San Gimignano, he helped us pick a great winery for lunch.and was able to squeeze in another winery stop for a tasting on our way back to Florence. He also took us on a backroads tour through the Chianti Classico area so we really were able to see and appreciate the amazing area rather than just driving in and out of a winery.

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