4.5 star rating: Recommended 10 Reviews

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

Highlights

  • 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 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.

Veronica

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.

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.

4 star rating: Recommended November 2012

A great way to see the Tuscan countryside without driving! Loved that it was a small group (8 maximum). visit a winery, a small village and a spectacular home-cooked full Italian meal. Worth the price.

2 star rating: It was OK, but could have been better June 2015

First the good:
The guide/driver was excellent
San Gimignano was everything we expected

Then the not so good:
The tour spent an excessive amount of time at the wine tasting
Monteriggioni, a perfectly preserved medieval town was hardly perfectly preserved, every available building within the walls was utilised either as a tourist trinket shop or an Osteria. Far too touristy!
The classic Tuscan dinner at a local farmhouse turned out to be at a commercial restaurant where our small group was joined by over 100 people from other tours. The meal was probably the worst food we had in a month in Italy.

2 star rating: It was OK, but could have been better October 2013

We never saw the sunset which is why I took this tour; I've been to San Gimignano twice before. Our guide seemed overly fond of the Querciavalle winery and we spent an inordinate amount of time there. I enjoy Chianti but was not impressed with theirs.

From USD $ 168.87

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Tour code: 5493CHIANTISUNSET

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