Siena, San Gimignano & Chianti small group tour with wine and lunch

In a group of only 8 people or less, Avventure Bellissime will drive you through the gorgeous Chianti countryside in the comfort of a Mercedes AC mini-van. Along with your expert driver-guide, you’ll stop to spend time in the city of Siena, before making your way to have lunch at a Chianti winery. Then it is on to San Gimigano, aTuscan hill town and its medieval architecture before traveling back to Florence via Castellina a charming village of the Chianti region

Highlights and what's included

  • A/C Mercedes vehicle or similar make
  • Local Expert English Speaking Driver-Guide
  • Pick up and Drop off in Florence city centre
  • 2 hr tour with licensed english speaking guide in Siena
  • 1 full wine tasting with light lunch in a selected winery in the Chianti area
  • Visit of San Gimignano
  • Visit of Monteriggioni and Castellina in Chianti


Why book an Avventure Bellissime tour?
Our tours offer you a more personalised and in-depth experience. This tour of Siena, San Gimignano and Chianti starts at 9am and runs until 6pm in the evening. You will have all the time you need to experience the beauty of the countryside.

Since you are in a small group, our very experienced English speaking driver -guides have far more time to interact with you and answer any questions you may have.

Let’s take a look at what your tour will include:

With your Avventure Bellissime driver-guide, you and your small tour group will leave from Florence city centre t 9am, and from there you’ll drive through the gorgeous Chianti countryside. The first stop is at Siena – a beautiful Tuscan hill town with its famous Piazza del Campo ( Campo Square ) , where the famous Palio , a horse race , is held twice a year - spend time in Siena touring the city and experiencing its medieval narrow streets.

Lunch at a Chianti winery
From Siena, we’ll then drive to a well-known winery in the Chianti area - Monterinaldi or similar, spending two hours or so there. You’ll be able to find out a little about how the popular wines for this region are produced. And then, it’s time for lunch! You’ll enjoy a selection of Bruchettas, salamis and cheeses accompanied by three superb chianti wines plus vinsanto.

San Gimignano
After lunch we will then travel to San Gimignano one of the most charming and picuresque Tuscan hill towns. It boasts medieval towers that were built for the richest families of that period. You can visit the cathedral, climb the ‘Torre Grossa’, take pictures of the stunning scenery which will be surrounding you and enjoy gelato in Cistern Square.

San Gimignano to Florence
After leaving San Gimignano, the tour returns to Florence via the Chianti area once again. We will stop at the medieval and charming villages of Castellina in Chianti and Monteriggioni, one of the most important and preserved walled castles in the area. Such was its importance – it was mentioned in Dante Alighieri in his most famous work - the Divine Comedy.

Other info

  • This tour is not fully accessible for wheelchair users or people with walking disabilities. However, please contact us directly and we will be able to take you on alternative routes suitable for you.
  • Tour operates with a minimum of 4 participants.
  • Meeting Point

    Your Small Group Tour of Siena, San Gimignano & Chianti will start from directly outside the Cafe Paskowski in Piazza Repubblica in Florence where you will find your guide holding a sign with Avventure Bellissime written on it

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    (6) Average Rating:


    Reviewed by Richard on
    We had a fantastic tour of San Gimignano and Sienna with Lorenzo. Everything went excellently -- the vehicle was spacious, Lorenzo was very knowledgeable and helpful at every occasion. The four of us on the tour enjoyed it greatly. Lorenzo also make a suggestion for dinner in Florence that turned out to be one of our best meals in Florence. Overall at great experience.
    Reviewed by Stacey D on
    We traveled in April with a group of eight, four adults and four kids. Our driver Jonathan was great and gave us a real feel for the area. We opted for lunch in the Vineyard which was an experience we will never forget. Jonathan was always willing to pull over so we could take a picture or just enjoy the sights. He also knew where the good gelato was!
    Reviewed by John and Lynn on
    We have just spent a wonderful day in the CHianti wine region with your wonderful tour guide JOacquin. He was courteous,knowledgeable,drove very well and went beyond our expectations and made this day very special! Thank you very much!
    Reviewed by Lisa - 12 October 2013 on
    We had a wonderful day. The driver was friendly, safe, and informative. We have two young children and he was also entertaining to them. The wine tour was nice and we also liked out winery guide very much. All around well done! Thank you!
    Reviewed by Dennis - 2 November 2013 on
    Excellent,Johnathon very knowledgable,friendly & spoke very good English.Lunch& wine tasting very good.DC
    Reviewed by Leane - 15 October 2013 on
    This was a great tour. The tour guide was full of knowledge of the area (as well as some lesser known facts) and I had a great time.

    thanks very much
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