Bestseller

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

4.85

4.8(429 reviews)

Private Tour

8 hours

Mobile ticket

Show all 23 photos

Overview

8 hours

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 (just if you won't 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 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.

* Would you like to have a traditional Italian meal’s experience? We can organize lunch in wine cellars or in the farms. This is a highly recommended experience, especially for the wine lovers.

Additional Info

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

What To Expect

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 that will allow you to taste or taste local food or buy some gifts!

2 hours • Admission Not Applicable

San Gimignano

*Option to organize lunch at a Farm/Winery for home made lunch with wine tasting (to be payed on site). We have several options about wineries. (This option will reduce the time in the cities of Siena and/or San Gimignano and exclude Monteriggioni).

2 hours • Admission Not Applicable

Options

da 3 a 7 persone

Mercedes luxury minivan Pickup included

What‘s Included

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

mance

Licensed Guide in Siena

Pickup points

Select a pickup point

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Reviews

4.85

429 reviews

Total reviews and rating from Viator & Tripadvisor

396

daytime trip in...
Carmen A,Jun 15, 2026
- Review from Viator
5.00
daytime trip in comfortable car with an exceptionally attentive guide, Simone. plenty of time to explore Siena and San Gimignano. The lunch in a private winery was certainly the best part of the trip. highly recommended
The most perfect day!
Em V,Jun 10, 2026
- Review from Viator
5.00
This tour was one of the highlights of our trip to Italy. Sienna and San Gimignano were just beautiful, each with their own unique charm and stunning scenery, giving us a wonderful taste of the region. Our driver, Marco, was fantastic. He was so relaxed, friendly and great to chat with throughout the day. It was an absolute pleasure to spend the day with him. He went above and beyond to arrange a lunch reservation at a truly magical spot after explaining that the restaurant I had originally requested would reduce our sightseeing time due to its location. His local knowledge and thoughtful recommendations made the entire experience even more special. The winery for lunch was absolutely incredible—the scenery was straight out of a movie. The setting, the food and wine and the atmosphere exceeded all of our expectations. This was the perfect way to see some of the region. It was an experience we will always remember. I would highly recommend this tour to anyone visiting Tuscany. Thank you Marco for such a special day!
Private Driver for a Siena, San Gimignano and Chianti Day Trip
Karin H,Jun 10, 2026
- Review from Viator
5.00
This was a great way to get out to the wine country. Our driver was nice and efficient. It was a great tour if you want a private driver to go Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence. If you want a tour guide, pick another tour. We just needed a driver.
Amazing day
Kyle B,Jun 8, 2026
- Review from Viator
5.00
Our tour guide was amazing and especially friendly to our kids. I would want Cosimo again if I had the chance
Perfect
Lauren R,Jun 1, 2026
- Review from Viator
5.00
Incredible day! This was such a beautiful day with such a knowledgeable tour guide. We were also able to add a stop based on our interests.
Great day trip from Florence!
Bill W,May 29, 2026
- Review from Viator
5.00
This was one of the highlights of our Italy trip. The Mercedes Sprinter van was comfortable, and the stops in Siena, San Gimignano, and the Tuscan winery were excellent. What made the day truly special was our driver, Fabrizio. He was knowledgeable, engaging, and went above and beyond by helping us secure a separate winery reservation. Traveling with our 15, 21, and 23-year-old children, he made the experience fun and memorable for everyone. The scenery, wine, and hospitality were outstanding. We would highly recommend this trip to anyone visiting Tuscany.
Lovely day in Siena and...
Grace S,May 21, 2026
- Review from Viator
5.00
Lovely day in Siena and Chianti with Marco. Excellent food and wine. Highly recommend this day trip from Florence.
Second time booking and it was fantastic!
Kerri J,May 18, 2026
- Review from Viator
5.00
This is our second time booking the same tour- JUST AS GOOD AS THE FIRST TIME !!!! AND- we'd book again the next time we visit.....not many places are worth this level or repeats. Thank you!!!!!
A very nice experience.
DAVIDADRIAN B,May 17, 2026
- Review from Viator
5.00
Leo is extremely attentive and speaks Spanish very well; everything was incredible, the visit to the towns of Tuscany was the best experience of our trip to Florence.
Recommended!!
Tatiana C,May 14, 2026
- Review from Viator
4.00
I loved that Marcos told us everything about the area and was very kind. The tour is definitely worth it; it was comfortable and the view is beautiful. The vineyard was fine, the sommeliers were very kind, but the food, as mentioned in other comments, also seemed very basic for the price. However, the wines are delicious. I went with my in-laws, who are people with reduced mobility, and everything went very well.