4.8 (440) · Florence · By Chianti Drivers private tours ▶ Watch the videoFree cancellation Private tour
Experience for your private party
Explore the art, culture, and medieval history of Italy on this private 8-hour 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 (only if you do not need a stop for lunch), 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 its main destinations. They will always share historical information, curiosities, and traditions about the sightseeing areas and are available for any needs.
Would you like to have a traditional Italian meal experience? We can organize lunch in wine cellars or on farms. This is a highly recommended experience, especially for wine lovers.
✓ Expert English-speaking driver✓ Bottled water✓ Onboard Wi-Fi (on request at reservation)✓ Air-conditioned vehicle✓ Private luxury car or minivan✓ Hotel pickup and drop-off in Florence✕ Full lunch + wine tasting at winery (to be paid on spot) from 50/70 euros per adult✕ Gratuity✕ Licensed Guide in Siena1 Siena
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, allowing you to taste local food or buy some gifts!
· 2 h
2 San Gimignano
Option to organize lunch at a Farm/Winery for homemade lunch with wine tasting (to be paid on site). We have several winery options.
This option will reduce the time in the cities of Siena and/or San Gimignano and exclude Monteriggioni.
· 2 h
3 Strada Statale 222 Chiantigiana
We explore the Tuscan countryside, driving through the Chianti hills.
Stop for pictures!
· Non-stop passage
4 Historic Centre of San Gimignano
Here we are in the beautiful stronghold of San Gimignano, frozen in the 1300s.
San Gimignano is a pearl of medieval architecture, famous for its tower houses!
This is our last stop of the day before returning to Florence.
· 2 h
Mobile or paper ticket accepted. One per booking.
Pick up from all hotels or apartments in Florence downtown
Please re-confirm the service the day prior via text, WhatsApp (+39 335 180 6522), or email info@chiantidrivers.it, and we will respond in a timely manner.
For last-minute bookings (less than 24 hours), please confirm at the same time.
Specialized infant seats are available. Infants and small children can ride in a pram or stroller. Suitable for all physical fitness levels. A maximum of seven people per booking. For 3 to 7 people Mercedes luxury minivan Pickup included Confirm your tour the day before to ensure smooth arrangements. Consider the lunch and wine tasting option for an authentic Tuscan experience. Wear comfortable shoes as you'll be walking in historic towns. Bring a camera to capture the stunning landscapes and medieval architecture. This tour is suitable for all fitness levels. For a full refund, cancel at least 24 hours before the scheduled departure time.
Product code: 23322P7
Activity offered by Chianti Drivers private tours via Viator.
WizardTrip Help Center Couples Families Small groups of friends Wine enthusiasts History buffs Private tour for your party Explore Siena, San Gimignano, and the Chianti region English-speaking driver with local knowledge Visit medieval towns and admire Tuscan landscapes Option for wine tasting and lunch at a farm Comfortable and luxurious private vehicle
Population 360,930 (2023)
Elevation 50 m
Currency euro
Official language Italian
Driving on the right
Power plugs C, F, L · 230 V
Emergency number 112
Capital city Rome Average temperatures 2° Jan 3° Feb 6° Mar 10° Apr 15° May 20° Jun 23° Jul 22° Aug 17° Sept 13° Oct 8° Nov 3° Dec Sources: Wikidata; climate: NASA POWER, 2001-2025 averages.
What is the duration of this private tour? + The tour lasts for 8 hours.
Can I arrange lunch and wine tasting during the tour? + Yes, you can organize lunch in wine cellars or on farms with wine tasting. This is an optional experience to be paid on site and may affect the time spent in certain locations.
What is the cancellation policy? + You can cancel for a full refund up to 24 hours before the scheduled departure time.
What is included in the tour? + The tour includes an expert English-speaking driver, bottled water, onboard Wi-Fi (on request), an air-conditioned private luxury vehicle, and hotel pickup and drop-off in Florence.
What is not included in the tour? + Full lunch and wine tasting at a winery, gratuity, and a licensed guide in Siena are not included.
How many people can be in a group? + A maximum of seven people can be in a booking.
Reviews provided by Viator, written by travellers on Viator and Tripadvisor.
★★★★★ Viator review
Touring Tuscany
Minnie_A, October 2026
Our day trip was AMAZING! Marco our guide and driver was very professional and nice to hang out with for 5 hours! He was patient and answered all of our questions! Took us to a very nice winery where we enjoyed lunch and wine tasting! All the sites visited were full of history! Loved all of it! We HIGHLY recommend!
★★★★★ Viator review
Sienna day trip from Florence
judi_m, October 2026
The drive to Siena is easy with a guide! The town is different and worth seeing! Cosimo was great! We felt safe and he knew the answer to every question! Highly recommend.
★★★★★ Viator review
Ask for Cosimos
Troy_Z, October 2026
We had the best experience today with Cosimos. It was one of the best days on any vacation I have been on. He speaks English beautifully and was so helpful with suggestions. We visited San Gimighano and experienced a family run vineyard and had a wonderful lunch and wine tasting and tour with lots of information and also met the owner. Then we visited Siena and toured the famous duomo de Siena and the surrounding village with shops, restaurants, etc. Such a beautiful experience. Theresa Z.
★★★★★ Viator review
Amazing Honeymoon Tour
JP3, October 2026
Amazing tour with my wife and I to celebrate our honeymoon. Tour guide was super useful and took many pictures of us as we discovered the Tuscany region
★★★★★ Tripadvisor review
A Beautiful Day in Tuscany
mickir260, September 2026
André was a wonderful driver…friendly, articulate, knowledgeable and engaging. We had expected him to accompany us at locations rather than just drop us off. The vehicle was first rate and comfortable even in the rear seat. We felt the price was too high for just transportation services. However, we did have a great day at all 3 stops and a lovely ride through the countryside.
Response from the operator · Info C Thank you very much dear!
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