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

Siena, San Gimignano and Chianti with Wine Tasting and Lunch

Product ID: 4511
Discover the wonders of the Italian countryside on this full day tour through the heart of Tuscany. Visit the medieval villages of San Gimignano and Monteriggioni, pass by the old town of Siena, and enjoy lunch and wine tasting in a Chianti winery.
About this activity
Duration: 11 hours
Starting time 8:30 AM
Skip the ticket line
Printed or mobile voucher accepted
Instant confirmation
Live tour guide
Spanish, English
Free cancellation up to 24 hours before activity starts

Select participants, date and language:



  • Visit two UNESCO World Heritage sites
  • Tour the beautiful Siena Cathedral, led by a local guide
  • Enjoy wonderful views of Tuscan rolling hills and Chianti countryside
  • Stop at a Chianti winery for lunch and a guided tasting of three different wines
7.5 hours
  • Florence

  • 1.1 hours
  • San Gimignano (free time)

  • 30 minutes
  • Monteriggioni (free time)

  • 10 minutes
  • Chianti Hills (lunch, winery)

  • 30 minutes
  • Siena (guided tour, free time)

  • 1.15 hours
  • Florence

Meeting point
Main stop
Other stop
Full description
Along the way that will lead you to Siena, stop at San Gimignano, a small and world famous walled town located on a hilltop, which remained intact through the centuries, renowned for its tall towers, wonderful frescoes and many other valuable works of art: here you will be led until the heart of the historical center, where you have free time at disposal for its fascinating discovery. Following San Gimignano,  stop at the charming historical hamlet of Monteriggioni, an amazing medieval village enclosed by its famous walls, which have remained standing to this day. Enjoy some free time to visit this village. Then, crossing the gently Chianti rolling hills, arrive at a small and typical winery where you will taste 4 fantastic wines and sample balsamic vinegar and locally produced delicacies.

Upon arrival in Siena, after free time for lunch (at your own expense until November 1, 2019, when lunch will be included), meet your local guide. Take a comprehensive guided tour of the historic center, starting from its most beautiful square, Piazza del Campo. Walk along the narrow medieval streets of the city, flanked by splendid palaces and historic shops, until you reach the Museum and Oratory of a Contrada (when open), where you can experience the atmosphere of the authentic and most intimate soul of the town.

The “Contrade” (districts into which the city is divided) are the real core of local social life, where inhabitants of each district compete with each other, as they devote themselves to the preparation of the famous Palio horse-race. The Museum of a ”Contrada”, as well as its Oratory, is therefore the heart of the district. It is an intimate and secret place containing historical documents and wonderful relics of the famous Palio, as well as magnificent works of art which are normally not disclosed to the public. If you wish, your tour can include a guided visit inside the famous Siena Cathedral, built in the 12th century, to discover the beauty of its treasures and works of art.
  • Transportation by air-conditioned bus
  • Multilingual tour escort on board
  • Professional local guide in Siena
  • Museum entrance fees
  • Wine tasting
  • Lunch
  • Siena Cathedral guided visit with entrance ticket (if option selected)
What’s Not Included
  • Hotel pickup and drop-off

Prepare for the activity

Meeting point

Piazzale Montelungo (Montelungo Square), in front of the yellow sign with the local partner's name on it.

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Important information
What to bring
  • Comfortable shoes
Know before you go
• The escort service is provided by professional multilingual tour leader
• The local guide service could be provided in two languages
• Please note that the order of the visits may change
• If the tour or the language cannot be confirmed, you will be offered an alternative or a full refund
Customer reviews

Overall rating

4.3 / 5

based on 69 reviews

Review summary

  • Service
    4.3 / 5
  • Organization
    4.3 / 5
  • Value for money
    4.1 / 5
  • Safety
    4.5 / 5
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It was a very big day, with lots packed in. We loved San Gimignano and would have liked more time there. Perhaps if the brief stop at Monteriggioni was eliminated, we could have spent more time at San Gimignano. Siena is a beautiful city, and we appreciated having a little free time before a guided tour of the highlights of the city - thoroughly enjoyable and very interesting. A disappointment for us, however, was the lack of guidance. The tour guide travelling with us did provide us with some general, historical information en route to our stops, but she did not guide us through San Gimignano, Monteriggioni or Sienna at all. The guide who showed us Siena was introduced to us after our free time there, and only stayed with us for about an hour or so. It would have been much better to have been shown some of the highlights of our other stops, rather than just letting us wander freely without knowing what we were looking at! Our stop at a local winery was very enjoyable and tasty!

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October 16, 2019

The tour was quite good though the group was rather large. Sara, our guide, bravely shepherded us through three towns. She was excellent - very friendly and caring. The balance between guided sightseeing and free time was good. The wine tasting was a bit of a disappointment. We really wanted to buy some wine for our one week stay in Florence, but we did not find the wines as good as what we had in restaurants.

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May 30, 2019

Fabulous day.. guide and driver perfect ...great value for money *****

Fabulous day seeing tuscany and visiting local towns. Guide on bus was professional and informative and driver very competant. Could have possibly stayed a little longer in San Giamano not a great deal of time to explore perhaps another half hour bearing in mind the queue for the famous ice cream shop ! Sienna was fabulous and the guided walking tour perfect our guide brought the city to life on the tour with her knowledge of sienna and local history.It was the build up to the paleo horserace when we arrived so the city was buzzing again perhaps another 15 mins allotted would be good as it was a little rushed to find a restaurant and have lunch before the tour started. Our next stop Greve in Chianti provided time for refreshment and then on to the wine tasting which rounded off the day perfectly. All in all the tour was well presented and well organised the time spent on the bus was minimal and the day went over too quick..well worth it and would def recomend to anyone. Loved the day !

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July 8, 2017

Organized by

CAF Tour & Travel

Product ID: 4511