Tours/Florence/Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence
Viator · Private tour

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

4.8(433)Florence1 hour
VIATOR4.8(330)TRIPADVISOR4.9(103)

Description

*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.

Tour Options

da 3 a 7 persone
  • Mercedes luxury minivan Pickup included

Itinerary

120 min

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!

120 min

*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).

Pass by

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

120 min

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

Highlights

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

What's included

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
Not included
Full lunch + wine tasting at winery (to be paid on spot) from 50/70 euros per adult
mance
Licensed Guide in Siena

Pickup Locations & Times

Pick up from all hotels or apartments in Florence downtown

Traveller Ratings

4.8
433 reviews
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399
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13
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Important Information

  • 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

Reviews(433)

K
Kariann_A
August 6, 2026
I thought it was pricey...

I thought it was pricey since all we basically had was a driver to the three locations. I was expecting him to be flexible go on country road to take pictures of scenery etc. he did not speak good English even though we request English speaking. The two towns were amazing but an hour at each place is Not enough. The winery was amazing amazing

Operator response

Hi Kariann, You booked a Siena San Gimignano tour and not a Chianti tour, that's a whole different story! If you want to see Siena and San Gimignano, there won't be much time for anything else! The drivers all speak proper English, I don't know what you were expecting. Sergio speaks good english and makes that since so many years! He has been at your complete disposal anytime, explaining in Siena and at winery...very strange to hear your words....

T
Thomas_F
July 23, 2026
This was an amazing day...

This was an amazing day trip. Our driver Simone was super friendly and knowledgeable and he was flexible with the itinerary. We got to stop at additional places on the way to the main stops for photos and we even went to a winery we have been keen to visit for ages. Would recommend this for couples or small groups.

Operator response

thank you so much Thomas!

R
roxyd877
July 13, 2026
The Perfect Tuscan Day: Incredible Winery & Guide

Simone picked us up on time. He guided us to our destinations as planned on time. It was hot time of year but he had the car AC cooler than we’ve had the entire trip. It was such a nice break away fro the heat. Some people reviews this was more of a driver than a guide. However, we would have never discovered these places without him. Very knowledgeable, professional and kind! It was expensive for two people and knowing this experience was for up to a group but happy with entire day and was worth it in the end. The winery experience was the best! We paid for light lunch and tasting. It exceeded our expectations, TERRE DI SOVERNAJA in San Gimignano and other fun stops!

Operator response

Thanks for your review, we are proud of our drivers and what is said about them. Than you again and see you next time dear!!!

H
Heidi_D
July 3, 2026
Beautiful scenic day trip to Siena

Our trip to Siena was fabulous and Cosimo made the day extra special. He was super knowledgeable and we enjoyed the special day!

Operator response

thank you so much

C
Carmen_A
June 15, 2026
daytime trip in...

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

Operator response

thank you dearest!!!

E
Em_V
June 10, 2026
The most perfect day!

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!

Operator response

We're happy to read your thoughts about us. It's our mission! Marco will appreciate that! Thank you

K
Karin_H
June 10, 2026
Private Driver for a Siena, San Gimignano and Chianti Day Trip

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.

Operator response

Thank you Karin!!!!

K
Kyle_B
June 8, 2026
Amazing day

Our tour guide was amazing and especially friendly to our kids. I would want Cosimo again if I had the chance

Operator response

very cool!!! thanks

L
Lauren_R
June 1, 2026
Perfect

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.

Operator response

Thank you Lauren!!

B
Bill_W
May 29, 2026
Great day trip from Florence!

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.

Operator response

Fabrizio is super!!! All my drivers are really good!! Very happy about your daily tour feedback

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