Day trip

Chianti and San Gimignano Sunset Tour from Siena

4.7 / 5

18 reviews

Activity provider: Tuscan Escapes by Papilio

Chianti and San Gimignano Sunset Tour from Siena

Activity provider: Tuscan Escapes by Papilio
Likely to sell out

From US$ 157.04 per person

Likely to sell out

Discover the beautiful wine land and villages of Chianti on a 9-hour small group tour from Siena. Taste the wines and food of Tuscany at a Chianti winery and organic farm. Watch the sunset over the towers of the medieval village of San Gimignano.

About this activity

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Covid-19 precautions
Special health and safety measures are in place. Check your activity voucher once you book for full details. Learn more
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
  • Sample the famous Chianti Classico red wine of Vernaccia
Full description
Explore the notable wine region of Chianti 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. See dense forests of oak wood and cypress trees, 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 Chianti Classico wines and olive oil. Next, descend to the medieval fortress of Monteriggioni, and marvel at its intact ring of walls and turrets. Built in the 13th century, Monteriggioni was mentioned in Dante’s “Divine Comedy.” As the sun begins to set, travel to the legendary village of San Gimignano to enjoy the romantic town after the daytime crowds have departed. Admire the medieval towers at a leisurely pace, and enjoy some free time to visit the cathedral or Civic Museum. Shop for souvenirs in the many leather and hand painted pottery stores. Sample the local produce at food shops and wine bars. Depart San Gimignano for a Tuscan dinner at an organic farm in the countryside. Taste the wines of San Gimignano, such as the notable Chianti red, Vernaccia. Weather permitting, dinner will be served on a terrace overlooking the cultivated fields and skyline of San Gimignano. Watch the sunset as you dine, before your return transfer to Siena.
  • Transportation by comfortable, air-conditioned vehicle
  • English-speaking wine expert guide
  • Chianti winery tour and wine tasting
  • Tuscan dinner with wine at an organic farm
  • Hotel pick-up and drop off
  • Tips and gratuities
Covid-19 precautions
Safety measures in place
  • All areas that customers touch are frequently cleaned
  • You must keep social distance while in vehicles
  • The number of visitors is limited to reduce crowds
Traveler requirements
  • You are required to bring and wear a mask

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

  • Please note that this is a small group tour of no more than 8 people
Customer reviews

Overall rating

4.7 /5

based on 18 reviews

Review summary

  • Guide
  • Transportation
  • Value for money
  • Safety

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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

Danielle was just a spectacular host. One could feel his passion and love for the region he calls his home. The selection of the vineyard and the dinner location were superb! I went backt to visit both of them after and would never have found them on my own. Beforehand, I was a bit sceptic about the touristic aspect of the tour, but it turned out to be super casual and didn‘t feel touristic at all. Time went by fast and I have not met such a knowledgeable person for a long time. Some historical anecdotes, but especially the knowledge about wine making around the world (if I remeber correctly, he actually studied wine-making in the past) were what made this event well worth the money.

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September 26, 2022


Product ID: 47303