4.5 star rating: Recommended 13 Reviews

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  • Location:Siena, Italy
  • Duration:8 hours 30 minutes (approx.)

Small-Group Chianti and San Gimignano Sunset Trip from Siena

On this afternoon and evening tour from Siena to Chianti and San Gimignano, explore the beautiful Chianti region – an area rich with dense oak forests and cypress trees – and discover its famous wine cellars. Then head to the UNESCO World Heritage-listed town of San Gimignano after the day’s crowds have dispersed. During the sunset, dine in a beautiful farmhouse overlooking the San Gimignano towers and the rolling, vine-covered hills.

Numbers are limited to eight people on this small-group tour, ensuring you'll enjoy personalized attention from your guide.


  • 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

Your small-group tour begins in the afternoon with a comfortable drive in a luxury minivan from Siena to Chianti -- a region of Italy famous for its beautiful vineyards and landscapes shaped into works of art by the combined actions of nature and man. Arrive first in the village of Castellina in Chianti, and enjoy a gelato (own expense) as you walk through its medieval alleyways and town center with your guide.

From here, enjoy the drive to a Chianti wine estate, where you'll tour the grounds and wine cellars while learning about the winemaking process. Sit down and savor a tasting of Black Rooster Chianti Classico wine and olive oil (included).

Then head to Monteriggioni, a perfectly preserved medieval town with a complete ring of walls and turrets built in the 13th century. It was Siena’s main bastion of defense against the armies of Florence during the Middle Ages, and today it is a quiet hamlet. Enjoy leisure time here to explore the charming city on your own.

In the late afternoon, arrive in San Gimignano and explore this romantic town of towers. You'll have free time to enter its impressive church, the Collegiata di San Gimignano, or explore the Civic Museum (entrance fees at own expense). Alternatively, shop in the artisan boutiques for leather goods and hand-painted pottery; sample the fruits of the soil in the food shops and wine bars; or discover the town’s many hidden beauties.

After your time in San Gimignano, head out of town to a nearby rustic farmhouse, where you'll be treated to a classic Tuscan dinner, accompanied by tastings of Vernaccia (the famous white wine of San Gimignano) and red Chianti wine. Your Tuscan dinner, consisting of cured meats, home-grown vegetables and cheeses, will be served on a terrace overlooking the cultivated fields and the ‘skyline’ of San Gimignano’s towers during sunset. As your tour comes to an end, meet your guide back at the minivan for the relaxing return journey to Siena.

Customer Reviews

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.

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.

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.

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.

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.


5 star rating: Highly Recommended November 2012

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

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.

4 star rating: Recommended October 2015

This tour was worth the price. Elena and Milo were wonderful guides- informative, funny and answered any and all questions with a wealth of knowledge about the Tuscany area. The winery and farm dinner were by far the highlights of the tour.

Sonja N
South Africa

4 star rating: Recommended September 2013

We enjoyed this tour very much, wine tasting and San Gimignano was our favourite parts. Milo was an absolute star, very knowledgeable about tuscan wines. I wish we had more time because I would have loved to do another tour with them. We never visited Monteriggioni which was very disappointing.

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Tour code: 5493CHIANTISUNSET


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