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

PRIVATE Day-Trip Siena, San Gimignano and Chianti from Florence

5.0(259)Florence1 hour
VIATOR5.0(36)TRIPADVISOR5.0(223)

Description

• EXPERIENCE FOR YOUR PRIVATE GROUP • Enjoy an exclusive 8–9 hour private tour of Tuscany from Florence with a professional local driver-guide. Travel through the scenic Chianti wine region and explore the medieval gems of Siena, San Gimignano. Visit iconic sites such as Piazza del Campo in Siena, famous for the Palio horse race, stroll among the medieval towers of San Gimignano (UNESCO site), and soak in the authentic atmosphere of the Tuscan countryside. Upgrade your experience with an optional wine tasting or an optional traditional lunch at a local organic farm or winery. • 8/9-hr Full-Day private tour of Tuscany • Visit the medieval cities of Monteriggioni, San Gimignano and Siena • Hear live commentary of the winery by your guide • Taste Craft Chianti Classico wine at a local vineyard (option) • Hotel or private address pick-up & drop-off Perfect for couples, families, and small groups looking for a relaxed, authentic, and fully private Tuscany experience.

Tour Options

Private Group
  • Pickup included

Itinerary

120 min

Siena is one of the most popular and visited places in Tuscany. It is known throughout Italy for its distinguished medieval architecture. Upon arrival, explore its rich history and art, through its notable local monuments such as the famous seashell-shaped Piazza del Campo and the outstanding Siena Cathedral. Many local shops fill the historic streets of Siena, a great opportunity for you to taste local food or buy some gifts!

Pass by

The Cathedral of Santa Maria Assunta is the main location of Catholic worship in Tuscany, and the diocese of Siena. The building is located in the square of the same name in the center of the city. Built in Italian Gothic style, it is one of the most significant and spectacular churches built in Italy.

Pass by

Piazza del Campo (or simply, il Campo) is the main square of the city of Siena. Unique for its particular and original seashell shape, it is renowned all over the world for its beauty and architectural integrity, as well as for being the place where the Palio di Siena takes place twice a year.

90 min

Make a lovely stop in the small, fortified village, which is still surrounded by its original medieval walls. Located not far from Siena, Monteriggioni is a great spot for a short walk after lunch at one of the local restaurants.

Admission not included120 min

*OPTIONAL lunch at an organic winery. Have lunch at a wonderful organic/biodynamic farm/winery in a beautiful setting overlooking the medieval towers of San Ginmignano. Enjoy a unique culinary experience while admiring an extraordinary Tuscan panorama among olive trees and vineyards. You will taste organic specialties, such as typical fresh pasta with traditional sauces, crostini, local meats and cured meats, legumes, seasonal vegetables, honey and cheeses seasoned with an incredible balsamic vinegar. The wine "Super Tuscan, Chianti, and Vernaccia" will accompany this lunch at every stage of the journey. Each of the four main courses and dessert will be paired with a different and distinctive glass of wine. We will conclude with a fabulous dessert. Allergies or special diets will be handled without problems by the company, upon your request at the time of booking. (This option will reduce a little the time in the cities of Siena and San Gimignano and will exclude Monteriggioni Fort).

90 min

The beautiful stronghold of San Gimignano is one of the most popular tourist attractions in Tuscany. San Gimignano is a treasure of medieval architecture, frozen in time at 1300 AD. Above all, it is famous for its ancient towers, which still stand out from its skyline, earning it the nickname Manhattan of the Middle Ages. Don't forget to stop by the famous Dondoli ice cream shop, winner of many awards for the best ice cream in the world. This is the last destination of the day, before returning to Florence.

Highlights

English-speaking licensed driver
On-Board WiFi
Unlimited cold mineral water
Free time in Siena and San Gimignano
Private transportation by MiniVan, Air-Conditioned
Pick-up and drop-off at your selected hotel/location (in Downtown Florence)

What's included

Included
English-speaking licensed driver
On-Board WiFi
Unlimited cold mineral water
Free time in Siena and San Gimignano
Private transportation by MiniVan, Air-Conditioned
Pick-up and drop-off at your selected hotel/location (in Downtown Florence)

Pickup Locations & Times

You will be picked up directly at your hotel or address (in Florence Down Town) communicated at the time of booking at the start time of the tour. Upon request, you can change your pickup time (24hours before) We do not pick-up at train stations or airports.

Traveller Ratings

5.0
259 reviews
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258
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Important Information

  • Infants and small children can ride in a pram or stroller
  • Public transportation options are available nearby
  • Specialized infant seats are available
  • Suitable for all physical fitness levels
  • In case of rain the umbrellas are provided by your driver.
  • Kindly share your mobile number for an easy communication during the pickup
  • This tour/experience will have a maximum of 6 travelers (your private party).
  • With agreements during the reservation we can organize lunch in winery, this is a highly recommended experience, especially for the wine lover. Dedicated lunches for people with cilia, allergies or vegetarians. (This option will exclude the possibility to visit the fortress of Monteriggioni). **Lunch in winery available (as an option on request) at an extra cost 55€pp to 65€pp per person. **
  • Departure is suggest at 9:00am. Pick-up time can be choise during the reservation
  • Authorized guide not included
  • Minors under 18 years old are not allowed to drink alcohol (wine tasting)

Reviews(259)

T
ThisGirlCanTravel
July 2, 2026
Perfect day exploring Tuscany

From planning right through to drop off, Alessandro made everything run so smoothly. He adjusted the itinerary to meet our wishes and recommended a picturesque spot for a delicious lunch. We didn’t feel rushed. The vehicle was comfortable with air conditioning during the heatwave and we had great conversation about wine, history, and the little villages and towns that we visited. Thank you Alessandro for a fantastic day!

5
569katier
June 24, 2026
Wonderful Tuscan Tour

We had a wonderful day visiting the beautiful Siena, then an amazing wine tasting and lunch at a small winery and finished off in San Gimigano. Alessandro our guide was very responsive and had great tips. He was informative and personable!! Would highly recommend this fantastic tour.

N
Nightshade2424
June 19, 2026
Perfect Day!

Our tour guide , Alessandro, made sure we had a perfect day! He was timely, friendly and informative. His van was luxurious and made the trip very comfortable. He recommended some great restaurants and we tried ll Vezzo which was the best food we had in Florence!!

M
Melissa P
June 13, 2026
What an amazing day!!

Alessandro created an incredible day with our requests in mind. He was well prepared and timely. We saw everything and avoided the summer crowds. The van was so nice and spacious. I will definitely work with him again.

N
N3333HCheatherf
May 28, 2026
Great day trip experience!

Our guide, Alessandro, was excellent and was very knowledgeable about the region, history and best places to visit in the towns. He found nice driving routes for sight-seeing in the Tuscany countryside and was a true pleasure to spend time with!

U
U8298NAlindaw
May 28, 2026
Winery day in Tuscany

Alesandro was an amazing guide for the day. Great experience, the winery lunch well worth it, and the entire day was one of the best!

P
Phyllis_K
May 17, 2026
Delightful Day Trip

Great day spent seeing the Tuscan countryside and ancient cities. Alessandro was a wonderful and knowledgeable driver.

T
Traveler06655780821
May 13, 2026
Amazing Driver and Tour of Tuscany

We came to Florence for the first part of our honeymoon and wanted to do a day trip around Tuscany. We booked this tour with Alessandro and had a fantastic time! We liked that he picked us up and dropped us off at our hotel. His car was very comfortable, and he was a great host - teaching us about the history of Tuscany, Florence, wine, and olive oil making! We went to both Siena and San Gimignano, and nothing ever felt rushed - the pacing was perfect. We liked that the itinerary was chill, with free time to roam ourselves in the towns. He even provided recommendations of places to see. Additionally, we had lunch and a wine tasting at a winery - the views were straight out of a movie! He even gave us recommendations for places to eat and drink in Florence when we came back. 10/10 would recommend!

D
Daniel A
May 7, 2026
Great driver and guide

Alessandro was a fantastic driver with great local knowledge and recommendations. Very attentive, courteous, friendly!

S
Scenic66929249560
April 27, 2026
Great Day!

Exceptional! So knowledgeable and fun!

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