Small-Group Chianti and San Gimignano Sunset Trip from Siena

Siena, Italy

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.

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.

USD $172.00

Traveler Reviews

Review by:   Holiday 87,    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. _br/_ Thank you to our guide Eleanor!

Review by:   pbmolgaard,    September 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.

Review by:   Robert S,    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!

Review by:   Annette P,    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.

Review by:   Constance E,    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.

Review by:   James B,    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_br/_ It was outstandingly good and Marella Favruzzo is a superb guide.

Review by:   Linda T,    July 2015
He entire tour was wonderful.

Review by:   Tony B,    June 2015
First the good:_br/_ The guide/driver was excellent_br/_ San Gimignano was everything we expected

Review by:   mike.elgin,    June 2014
Great tour guide - very friendly and knowledgable. Awesome views of the countryside. Winery/dinner was really awesome.

Review by:   Nancy L,    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.

Review by:   Sonja N,    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.

Review by:   Laura I,    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.

Review by:   anne c,    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.

Review by:   Veronica T,    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.

Review by:   Larry D,    November 2012
The guide was full of knowledge about the region. The farmhouse meal was superb.

Review by:   Gale O,    September 2012
Amazing! Rain and all our guide Made the outing enjoyable. I will take this tour again next year with my friend.

All Traveler Reviews...