Day trip

San Gimignano, Siena, Chianti Guided Tour from Florence

San Gimignano, Siena, Chianti Guided Tour from Florence

From US$ 56.21 per person

Enjoy a full-day tour of Tuscany’s villages and wine regions in the heart of the Tuscan countryside. Visit San Gimignano and the medieval town of Siena.

About this activity

Free cancellation
Cancel up to 24 hours in advance to receive a full refund
Covid-19 precautions
Special health and safety measures apply. Learn more
Mobile ticketing
Use your phone or print your voucher
Duration 12 hours
Check availability to see starting times.
Instant confirmation
Live tour guide
Portuguese, English, Italian, Spanish, French
Private or small groups available

What customers loved


9.5 hours
  • Florence

  • 1 hour
  • San Gimignano (free time)

  • Monteriggioni Castle (free time)

  • Poggibonsi (wine tasting)

  • Siena (guided tour, free time)

  • 1.5 hours
  • Florence

Meeting point
Main stop
Other stop
  • Escape the bustle of Florence for a day and explore the beautiful Tuscan countryside
  • Drive through the gently rolling hills of the Val D’Elsa in luxury, air-conditioned coaches
  • Visit the medieval town of San Gimignano, home to Vernaccia di San Gimignano wine and saffron
  • Explore the immaculate town of Siena, world-renowned for its Palio horse race
  • Visit a splendid Chianti estate and take part in two exclusive wine tastings
Full description

Explore the heart of beautiful Tuscany on a full-day tour of the towns of San Gimignano and Siena, then discover the bucolic wine region of Chianti. Depart from Florence by an air-conditioned bus to your first stop, the UNESCO World Heritage Site of San Gimignano.

Discover one of the most splendid examples of an Italian medieval town. Distinguished by its famous towering skyline, San Gimignano stands along the Via Francigena on the hills of the Upper Val D’Elsa.

Get acquainted with the Tuscan environment with the town’s Vernaccia di San Gimignano wine, saffron, and Santa Fina pottery. Enjoy some free time to stroll through the town on your own and see its beautiful squares, architecture, churches, and side streets.

Afterward, head out to a unique location in the Chianti countryside to enjoy a wine tasting. Once you hop off the bus, be guided around a splendid winery. Get introduced to the estate's fascinating history and background.

Head inside the cellars to learn the secrets of Chianti winemaking together with the local host. Then enjoy a delicious wine tasting of Chianti Classico.

Continue to Siena for a guided tour of its enchanting architectural styles, including the Cathedral (exterior only) and Palazzo Comunale (Municipal Building, exterior only) in Piazza del Campo. The famous shell-shaped square provides the stage for the thrilling Palio horse race, run twice every summer.

  • Travel by GT coach or minivan with air conditioning
  • Expert multilingual tour leader
  • Guided tour of Siena with a monolingual guide (in English and Spanish only)
  • Free time in San Gimignano
  • Visit to the Monteriggioni fortress
  • Wine tastings and guided visit at a Chianti estate
  • Visit to the interior of Siena Cathedral
  • Visit to the interior of Palazzo Comunale
  • Lunch
Covid-19 precautions
Safety measures in place
  • All areas that customers touch are frequently cleaned
  • You must keep social distance while in vehicles
  • The number of visitors is limited to reduce crowds
Traveler requirements
  • You are required to bring and wear a mask
  • You must fill out a travel information form
  • All participants who are 12 years and older must present a Reinforced Green Pass that is valid in the EU and has a verifiable QR code. Reinforced Green Passes can only be obtained by uploading either proof of full vaccination or proof of a Covid-19 infection within the last 6 months to either the Green Pass or Covid Certificate app
  • All participants must also bring a valid government-issued photo ID (e.g. passport, driver's license, etc)

Select participants and date



Meeting point

Meeting point varies depending on option booked.

Important information

What to bring

  • Comfortable clothes
  • Comfortable shoes

Know before you go

  • This tour will be conducted in multiple languages at the same time
  • Please arrive at the meeting point 15 minutes before departure time
  • The tour itinerary can be switched according to the season and due to organization issues, but you'll always visit all the stops
  • Customers must be able to climb and descend stairs
  • In the absence of the documents required for the COVID-19 security measures, it will not be possible to participate in the activity and no refund will be made
Customer reviews

Overall rating

4.4 /5

based on 2990 reviews

Review summary

  • Guide
  • Transportation
  • Value for money
  • Safety

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The towns are spectacular. It's a beautiful area, well worth seeing. The visit was a bit rushed, but if you want a convenient arrangement, where you don't have to worry about planning your trip, driving, finding a parking a spot etc., it's a good option. The driver Eddy was nice, spoke many language and also acted a bit as a guide during the drive. The only suggestion I have is advising the customers in advance that having lunch in Siena might be tricky when there are a lot of tourists around. It took us almost an hour to find seating and to be able to eat a prepackaged sandwich at a small cafe. Everything everywhere seemed all booked up. But otherwise, this day trip was the highlight of our weekend and we recommend it.

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November 2, 2021

Incredible tour with fantastic staff. Anastasia, Orlando, and Fabiano were so kind and attentive. I had my 3 year old daughter with me and she was welcomed by the group, and felt very comfortable. I forgot something in the bus at the end of the tour and the whole team went out of their way to arrange for me to get my belongings back. They could've said it's not possible, but instead, they made it happen! Truly grateful to the staff and this tour was one of my favorite activities in our 10-day trip to Italy. Would book with them again, and highly recommend them!

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October 17, 2021

Our guide was Luca and he was great! There were 8 of us, 3 of whom with English and Luca took care to divide the explanation into small parts in order to translate it for everyone. Fantastic tour, very well organized, definitely to rely on this company again if all the guides are as good as him!

June 7, 2021

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Product ID: 7679