• Location: Siena, Italy
  • Duration: 8 hours 30 minutes (approx.)
From USD $ 187.87 View price calendar

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Sip world-class wine and watch the sunset on this day trip to Chianti and San Gimignano from Siena. Led by an expert guide, try the local Chianti blends with a wine-cellar tour and tasting, and explore the medieval towns of Castellina and Monteriggioni. Then, head to the UNESCO-listed San Gimignano to see the sunset as you savor a traditional Tuscan dinner in a farmhouse overlooking the hills. Group size is reserved to eight people to keep the experience as intimate as possible. 


  • Sunset trip to Chianti and San Gimignano from Siena
  • Explore the vineyard-rich region of Chianti with your expert guide
  • Enjoy a wine-cellar tour and tasting of Chianti Classico and Vernaccia wines (included)
  • Spend time at leisure San Gimignano, a UNESCO World Heritage Site
  • Admire the sunset and stunning views of San Gimignano
  • Savor a classic Tuscan dinner at a local farmhouse (included)
  • Small-group tour with a maximum of eight people ensures a more personalized experience

What You Can Expect

Small-Group Chianti and San Gimignano Sunset Trip from Siena

Small-Group Chianti and San Gimignano Sunset Trip from Siena

Hop aboard your luxury coach in Siena and begin the journey to Chianti with your guide. As you go, learn more about the history behind this beautiful landscape as you watch the vineyards roll by from the windows.

Make your first stop in Castellina in Chianti for a relaxed stroll through the medieval streets with your guide. If your sweet tooth starts calling, stop to purchase an Italian gelato along the way.

Afterward, travel to a Chianti wine estate to learn about the production process while touring the grounds and cellars. Try a complimentary tasting of high-quality olive oil, accompanied by Black Rooster Chianti Classico wine.

Continue to the town of Monteriggioni, where you'll enjoy some free time to wander independently. As you explore, note the surrounding ring of 13th-century walls and turrets, which once served as Siena’s main line of defense against the Florentine armies.

Arrive in San Gimignano in the late afternoon, with free time to check out the Collegiata di San Gimignano, shop for hand-crafted pottery and leather goods or admire the medieval architecture and impressive towers.

Then travel to a rustic farmhouse just out of town for a traditional Tuscan dinner, complemented by red Chianti blends and tastings of San Gimignano’s famous white wine, Vernaccia. Watch the sunset over San Gimignano and the surrounding landscape while you’re served fresh vegetables, cured meats and cheeses out on the terrace.

After dinner, enjoy a relaxing trip back to Siena.

Customer Reviews

Holiday 87

5 star rating: Highly Recommended July 2017

The tour was fantastic...food,wine and guide. Myself and my friend did this as part of our stay in Siena, both of us in our late twenties. We were part of a small group of 6 and the group itself made the experience all the more enjoyable.
Thank you to our guide Eleanor!

Robert S

5 star rating: Highly Recommended August 2016

We loved this tour especially since we were the only two on it. Our guide Elena was wonderful and very knowledgeable. The owners of the winery were great and we loved the wine and food. San Gimignano was beautiful along with the castle. Dinner was out of this world!

Constance E

5 star rating: Highly Recommended September 2015

Five star all the way!! These tour leaders are fantastic, they are knowledgeable and fun and made it all very worthwhile. Would love to do a two day trip with them to a few more areas including olive oil tasting, cheese and balsamic.

James B

5 star rating: Highly Recommended September 2015

This is James' wife Penny. I reviewed this tour highly favourably and at great length on Trip Advisor. http://www.tripadvisor.co.uk/ShowUserReviews-g187902-d1778141-r308030413-Tuscan_Escapes_Day_Tours-Siena_Tuscany.html
It was outstandingly good and Marella Favruzzo is a superb guide.

Linda T

5 star rating: Highly Recommended July 2015

He entire tour was wonderful.


5 star rating: Highly Recommended June 2014

Great tour guide - very friendly and knowledgable. Awesome views of the countryside. Winery/dinner was really awesome.

Laura I

5 star rating: Highly Recommended June 2013

The tour was wondrful. Daniel and Sylvie were both interesting and informative and fun! We really saw many different sites and experienced the exellent food and wine. Would recomend this any time.

Veronica T

5 star rating: Highly Recommended November 2012

We were a group of four gals and our guide was delightful, spoke perfect English and was very knowledgeable. We would never have been able to see as much as we did without a guide. The farm where we ate dinner was beautiful, and the food and service were great.


Larry D

5 star rating: Highly Recommended November 2012

The guide was full of knowledge about the region. The farmhouse meal was superb.

Gale O

5 star rating: Highly Recommended September 2012

Amazing! Rain and all our guide Made the outing enjoyable. I will take this tour again next year with my friend.

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