1. Italy
  2. Tuscany
  3. Florence
  4. Palazzo Pubblico

San Gimignano, Siena, Chianti Guided Tour from Florence

Product ID: 7679
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 ticket
Duration: 11.45 - 12 hours
Starting time 8:45 AM
Printed or mobile voucher accepted
Instant confirmation
Host or greeter
Italian, Portuguese, English, Spanish, French
Free cancellation up to 24 hours before activity starts

Select participants, date and language:



  • 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
9 - 9.5 hrs
  • Florence

  • 1 hour
  • San Gimignano (free time)

  • Monteriggioni Castle (free time)

  • Poggibonsi (lunch, wine tasting)

  • Siena (guided tour, free time)

  • 1.5 hours
  • Florence

    • Entry not included
Meeting point
Main stop
Other stop
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 lunch and two wine tastings. Once you hop off the bus, you will be guided around the splendid estate; here you will be introduced to the estate's fascinating history and background. Then head inside the cellars where you'll learn the secrets of Chianti wine making together with the local host. Now you're ready to enjoy your delicious wine tasting of Chianti Classico and a typical lunch, and so the route will continue to the restaurant: your typical Tuscan lunch will be accompanied by two excellent products of the estate itself, a "Riserva" and an IGP wine. Take your time after lunch to relax in the villa's luxurious gardens.

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
  • Lunch consisting of typical Tuscan dishes (vegetarian menu available upon request)
  • 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
What’s Not Included
  • Visit to the interior of Siena Cathedral
  • Visit to the interior of Palazzo Comunale

Prepare for the activity

Meeting point

Get to the meeting point by getting on T1 Leonardo tramway to Villa Costanza (get off at Villa Costanza stop at the end of the line). It is a 20 minute ride from the city centre, you can get on at whatever stop is closest to you. Meet your guide at Villa Costanza, Florence Coach Station. Your guide will be wearing a green shirt.

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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 2923 reviews

Review summary

  • Service
    4.4 / 5
  • Organization
    4.3 / 5
  • Value for money
    4.4 / 5
  • Safety
    4.6 / 5
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It was a very pleasant and comfortable experience. We saw regions of Toscana that we couldn't have the opportunity otherwise and we have as much time we wanted to get a look at the cities and villages we went. The bus driver and our guide Paola were excellent and very very helpful in any info we wanted. Thanks Paola! :)

March 12, 2020

Wonderful ride! The food included was delicious and the time in the cities was sufficient. The guide Carmen was super friendly and helpful. The landscapes are wonderful. It is very worth it. I only suggest that they do not delay their departure, as it was winter, it got dark very early and some landscapes were lost.

January 7, 2020

The tour was nice. We specifically booked it so that we travel from Florence to Siena and stay there - but the company apparently has distinct winter and summer schedules, and also can change the itinerary at any time. So we visited Siena first, and had to take a public bus back to the city in the evening, after the tour ended. Would be helpful to highlight the disclaimer about potential changes in the itinerary. Lunch and wine tasting are done together, at a nice estate.

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January 6, 2020

Organized by

Tour and Travel Services SA

Product ID: 7679