San Gimignano, Siena, Chianti Guided Tour from Florence

San Gimignano, Siena, Chianti Guided Tour from Florence

From $70.90 per person

Enjoy a full-day tour of Tuscany’s villages and wine regions from Florence and travel into the heart of the beautiful Tuscan countryside. Visit the town of San Gimignano, the wine territory of Chianti, 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 687 minutes - 12 hours
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Instant confirmation
Live tour guide
Italian, Portuguese, English, Spanish, French
Private or small groups available

What customers loved


9 - 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. Departing from Florence by luxury air-conditioned bus, your first stop will be the UNESCO World Heritage Site of San Gimignano, one of the most splendid examples of an Italian medieval town. Distinguished by its famous towered skyline, San Gimignano stands along the Via Francigena on the hills of the Upper Val D’Elsa. Also famous for its Vernaccia di San Gimignano wine, saffron, and precious Santa Fina pottery, it is an excellent place to get acquainted with the Tuscan environment. You will enjoy some free time to stroll through the town on your own and explore its beautiful squares, architecture, churches, and side streets. Afterwards you will head out to a unique location in the Chianti countryside to enjoy a wine tasting. Once you hop off the bus, you will be guided around a splendid winer. Here you will be introduced to the estate's fascinating history and background. Head inside the cellars where you'll 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, again 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 escorts
  • Guided tour of Siena with 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

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The details below may change if you update your current selection:

    Meeting point

    Meeting point varies depending on option booked.

    Important information

    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
    Customer reviews

    Overall rating

    4.4 / 5

    based on 2955 reviews

    Review summary

    • Guide
    • Transportation
    • Value for money
    • Safety
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    Beautiful tour and great tasting. I recommend this tour to those who have little time and want to see a lot or to those who, like us, wanted to have an idea of what there is to see and do in order to organize a more targeted holiday in the future. We were a group of 2 families with children of 14, 9, 8, 7 years in tow who have withstood the walks in the various stages. The bus was very nice and clean and was especially appreciated by those who usually drive (my husband) and cannot enjoy the view.

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    October 12, 2020

    Guide Lucy gives a good explanation about the 3 picturesque towns that are visited. Therefore, the day was certainly a success. The wine tasting is a bit disappointing. A minimum of wine is poured and time is repeatedly indicated while you are eating and wine tasting. The group was nice so we had a good laugh about it.

    September 25, 2020

    A perfect day! Our guide was kind snd the tour very well done and organised. Each place with the exact time for enjoy and not get bored. And the lunch was amazing! I did the trip with my 2 years old son and he also enjoyed it and the guide brought a seat for the van and lunch for him as well. Excellent experience!

    September 22, 2020

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    Product ID: 7679