Day trip

Chianti and San Gimignano Sunset Tour from Siena

4.7 / 5

20 reviews

Activity provider: Tuscan Escapes by Papilio

Chianti and San Gimignano Sunset Tour from Siena

Activity provider: Tuscan Escapes by Papilio

From US$ 168.40 per person

Discover the Chianti and the town of San Gimignano on a small group tour from Siena. Taste the wines and food of Tuscany at a Chianti winery and farm and enjoy a typical local dinner with wine.

About this activity

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Duration 9 hours
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Live tour guide
Small group
Limited to 8 participants


  • Taste the wines of Chianti and the Chianti Classico wine region
  • Enjoy a dinner of typical Tuscan produce as you watch the sunset
  • Explore the medieval town and towers of San Gimignano
  • Go to the medieval fortress of Monteriggioni
Full description
Explore the Chianti wine region and the hilltop town of San Gimignano on a full-day sightseeing and wine tasting tour from Siena. Travel in a small group of no more than 8 people and enjoy comfortable transfers by air-conditioned vehicle. Depart Siena in the early afternoon, and drive past the vineyards of the Chianti wine lands: neat rows of vineyards, and landscapes shaped into works of art by the combined forces of nature and mankind. Go to a Chianti wine estate to tour the grounds and wine cellars. Learn the winemaking process before sitting down to a tasting of local Chianti wines and olive oil. Explore the medieval fortress of Monteriggioni and marvel at its intact ring of walls and turrets. Travel to the legendary village of San Gimignano to enjoy the romantic town as the sun begins to set and daytime crowds have departed. Admire the medieval towers at a leisurely pace, and explore the many streets and squares. Visit the boutique stores of local crafts and products for souvenirs. Enjoy a typical Tuscan dinner at a local farm in the countryside. Taste the white wine of San Gimignano, the Vernaccia, or have some local Chianti red wine. Weather permitting, dinner will be served outdoors. Return to Siena after dinner.
  • Entry tickets & places visited
    • Chianti Hills visit

  • Who you’ll be with
    • Live tour guide: English

  • Transport
    • Transport by van

  • Food & drink
    • Dinner

    • Wine tasting, water

Select participants and date



Meeting point

Meet your guide under the large tree at San Domenico Basilica, Siena

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Important information

Know before you go

  • Comfortable walking shoes are recommended.
Customer reviews

Overall rating

4.7 /5

based on 20 reviews

Review summary

  • Guide
  • Transportation
  • Value for money
  • Safety

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Star rating:

Guillermo was outstanding! Fun, knowledgeable and wonderful company.( and an excellent driver!) This tour covered so much of what you want to see and experience of the Tuscany country. The group size of 6 was perfect. The winery visit and farmhouse dinner were “bravissimo!” A highlight of our 2 week trip covering Rome, Siena and Florence.

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October 19, 2022

We loved this tour! Amber was super informative about everything and being from Siena was so passionate about the beautiful area, she really made the tour special. The van is comfortable and the wine tasting was really cool. We had a perfect amount of time to explore San gimignano and Monteriggioni. The dinner at the end is epic. Really appreciated them catering to me as a gluten intolerant person. Would highly recommend this experience!

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July 9, 2022

Beautiful countryside togeth tasting the finest wine and local product

The villages we visited were picturesque and wonderful. We had enough time to wander around. On the way the guide provided interesting information on history and the area. The visit to the chianti winery was lovely. It offered an excellent tasting and the farmhouse and grounds were an additional bonus of the visit. The dinner offered everything it promised and more and the location had a lovely view. They kindly took food dietary restrictions into account and offered a lot and tasty alternatives.

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May 12, 2019

Product ID: 47303