Day trip

From Siena: Chianti and San Gimignano Sunset Tour

4.7 / 5

21 reviews

Activity provider:Tuscan Escapes by Papilio
Day trip

From Siena: Chianti and San Gimignano Sunset Tour

Activity provider:Tuscan Escapes by Papilio
Likely to sell out

From US$ 171.75 per person

Likely to sell out

Discover Chianti and the town of San Gimignano on a 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 sightseeing and wine-tasting tour from Siena. Travel in a small group 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.

Head 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 village of San Gimignano to enjoy the charming streets and laneways 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. 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.

  • Transportation by comfortable, air-conditioned vehicle
  • English-speaking expert guide
  • Chianti winery tour and wine tasting
  • Tuscan dinner with wine at farm
  • Hotel pick-up and drop-off
  • Tips and gratuities

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Meeting point

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

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Important information

What to bring

  • Comfortable shoes
Customer reviews

Overall rating

4.7 /5

based on 21 reviews

Review summary

  • Guide
  • Transportation
  • Service
  • Organization

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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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May 31, 2023

Our guide was excellent and very knowledgeable and caring. The vegetarian food was very disappointing for 4 of us. Our main meal consisted of just 1 piece of aubergine slice 1 courgette piece and lettuce surely could do better than that in the heart of Tuscany.

May 31, 2023

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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May 31, 2023

Product ID: 47303