Siena, Italy
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clock-o8 hours 30 minutes (Approx.)
ticket-oMobile ticket
commentOffered in: English


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
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.


Viator Traveller's Reviews

16 reviews
5 Star
4 Star
3 Star
2 Star
1 Star
, Jul 2017

The tour was,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!

, Sep 2016

Enjoyed the tour quite a bit, but would have prefered a bit more wine tasting. The one winery we did go to was charming and the owner was great. The guides were very good. I did feel that the claim were having dinner in a farm house was just absurd it was a plesant, but relatively large, restaurant in the country.

, Aug 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!

, Oct 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.

, Sep 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.

, Sep 2015

This is James' wife Penny. I reviewed this tour highly favourably and at great length on Trip Advisor.
It was outstandingly good and Marella Favruzzo is a superb guide.

, Jul 2015

He entire tour was wonderful.

, Jun 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.

, Jun 2014

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

, Oct 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.

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Product code: 5493CHIANTISUNSET

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