Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence

8 hours
Pick-up offered
Free cancellation
1 - 7
Mobile ticket


*Experience for your private party*

Explore the art, culture and medieval history of Italy on this private 8 hrs tour.
Discover the delights of Tuscany on a private day trip from Florence.
With a knowledgeable English-speaking private driver, travel through the renowned Chianti wine region to visit the towns of Siena, the fortress of Monteriggioni and San Gimignano.
See world-famous landmarks like Siena’s Piazza del Campo, home to the annual Palio horserace, and the medieval hilltop towers of San Gimignano.

• 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.
* With agreements during the reservation we can organize lunch in wine cellars or in the farms. This is a highly recommended experience, especially for the wine lover.


This is a typical itinerary for this product

Stop At: Siena, Siena, Tuscany

Siena is known throughout Italy for the quality of its medieval architecture.
Upon arrival, enjoy the best local monuments such as the famous Conch-shaped Piazza del Campo and the outstanding 13th-century Siena Cathedral.
Many local shops fill the historic streets of Siena that will allow you to taste or taste local food or buy some gifts!

Duration: 2 hours

Stop At: Castello Monteriggioni, Piazza Roma, 53035, Monteriggioni Italy

Nice stop in the small fortified village of the medieval period, still surrounded by the original medieval walls.
Located a short distance from Siena Monteriggioni is a great place for us for a short walk after lunch at one of the local restaurants.

Duration: 1 hour

Stop At: Castellina In Chianti, Castellina In Chianti, Tuscany

*Option to organize lunch at the Farm or Winery, where you can taste wines and organic local products. (to be payed on spot)
(This option will reduce the time in the cities of Siena and San Gimignano and exclude Monteriggioni).

Duration: 2 hours

Pass By: Chianti Road, Italy

We explore the country of Tuscany, we will drive through the chianti hills. Stop for picture!!!!

Stop At: Historic Centre of San Gimignano, Piazza del Duomo 2, 53037, San Gimignano Italy

Here we are in the beautiful stronghold of San Gimignano. Freeze at the age 1300dc, San Gimignano a pearl of medieval architecture famous for its houses tower!
This is our last spot of the day before returning to Florence

Duration: 2 hours


  • 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


  • Lunch + wine tasting at farm house (to be paid on spot)
  • Guide city tour (you will find the complete tour with private guide in Siena on viator with this code 23322P50)

Additional information

  • Confirmation will be received at time of booking
  • Infant seats available
  • A maximum of eight people per booking
  • Not wheelchair accessible
  • Stroller accessible
  • Most travelers can participate
  • This is a private tour/activity. Only your group will participate

Ticket delivery

You can present either a paper or an electronic voucher for this activity.




For a full refund, cancel at least 24 hours in advance of the start time of the experience.

May 2022

Simone was a wonderful driver/guide for the day. He gave us information about each location we stopped at. We had free time to explore. It was an extremely flexible day. He even took us to a few extra stops on the way back to Florence.

May 2022

Hearing history of the area from our fantastic/driver, Ricardo. Having a wonderful lunch with lots of great food and wine! Seeing the beautiful Tuscan countryside and Siena and San Gimignano. Everything was excellent all day!

May 2022

Massimo was a wonderful guide and driver for the day. He gave us plenty of information and was extremely flexible throughout the day. He was so friendly as well. He also organized the perfect lunch and wine tasting in between our stops. My wife and I would highly recommend this to anyone.

April 2022

The farmhouse restaurant/winery we went to was beautiful with great wine and food- felt like a real Tuscan experience! I do wish my driver’s English was a little better

April 2022

We had a fabulous experience on our private tour! What a fantastic way to get a taste of Tuscany - our driver, Massimo, was incredibly knowledgeable and made great suggestions for how best to use our limited time in each place. He was also very flexible and gave us options so we could do exactl...

April 2022

Beautiful Tuscan country scenery. Our driver Marco was great, comfortable, friendly and informative. Loved Siena and San Gimignano, both were amazing. Highly recommend it. We stopped for a great lunch and wine tasting at Sant’Appiano which had great views of the Tuscan Valley. Out host Barbara an...

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from US$600.41 / per vehicle