Small-Group Chianti and San Gimignano Sunset Trip from Siena
Description
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 by visiting a local producer, touring their cellars and tasting their wines. Then head to the UNESCO World Heritage town of San Gimignano, famous for its medieval towers. Enjoy the main sights and browse the streets and boutique stores just as the day's crowds begin to dwindle. Visit a local farm and enjoy a farm-to-table dinner of its products and wines during sunset, in a stunning location overlooking the San Gimignano towers and the rolling, vine-covered hills.
Tour Options
Itinerary
Meet your tour guide at 2.30pm in front of the church of San Domenico in Siena and begin the tour with a comfortable drive through the Chianti countryside. Visit a Chianti wine estate, where you'll tour the grounds and wine cellars while learning about the wine-making process. Sit down and savor a tasting of Black Rooster Chianti Classico wine.
After visiting a Chianti winery, visit a historic town that was once of fortress, Monteriggioni, to marvel at the medieval towers that are still intact. Monteriggioni is a perfectly preserved medieval town with a complete ring of walls and turrets, once Siena’s main bastion of defense against the armies of Florence. Today it is a quiet hamlet and you can enjoy leisure time exploring the charming streets and stores of local crafts.
In the late afternoon, arrive in San Gimignano as the crowds begin to dwindle and the many streets and squares of this medieval town of towers that flourished thanks to the via Francigena, an important trade route. Enjoy free time to enter its impressive church, the Collegiata di San Gimignano, or to explore the Civic Museum (entrance fees at own expense). Alternatively, shop 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 wine. Enjoy the farm's products and wine over a convivial dinner with the others on tour that you can now call new friends.
Highlights
What's included
Traveller Ratings
Important Information
- Infants and small children can ride in a pram or stroller
- Public transportation options are available nearby
- Specialized infant seats are available
- Not recommended for travelers with poor cardiovascular health
- Suitable for all physical fitness levels
- Customers who have not reached Italy's legal drinking age of 18 will not be served alcohol
Reviews(64)
Wonderful visits starting with interesting winery led by very enthusiastic winemaker Robert. Good and interesting wines. Nice unguided stroll about San Gimignano. Followed by nice meal at Agro Tourism farm with meal and wine. And beautiful sunset view of Tuscany hills.
This was an amazing excursion! It was worth every penny! The tour itself was so informative and fun. The food and wine were great and it’s just the right size group. Highly recommend!
You must must must do a Tuscan adventure with these folks - our guide Keko was truly amazing - the stops, the history, the wine, the company was some of the best tours we have had - thank you Keko!
You must must must do a Tuscan adventure with these folks - our guide Keko was truly amazing - the stops, the history, the wine, the company was some of the best tours we have had - thank you Keko!
The tour was impeccable from beginning to end. Organised and professional. Our tour leader, Georgia, was knowledgeable, friendly, fun and accomodating. Highly recommend this tour to get a taste of a winery and authentic dinner in the evening. The winery tour and tasting with Juan was also super interesting and picturesque. Grazie Mille Georgia for the experience and sharing your obvious passion and knowledge of the region. Nicole and Chris from Melbourne, Australia. 26 July 2025 tour.
Oh my gosh! Where do I even begin?! This is EVERYTHING I wanted in a Tuscan wine tour! Gorgeous little stops at San Gimignano and Monteriggoni. A gorgeous Chianti winery tour and a beautiful Tuscan dinner cooked by a family who also served us their own wines made from the vineyard we ate on! But the highlight of our tour was our guide William! What an absolute ray of sunshine! He was so knowledgeable and gave us so many random facts and tidbits (my husband was in HEAVEN)! If you have the chance - do this amazing tour! The company, the services and William were spectacular and I can’t say enough good things about him! I hope we meet again! We got a picture with him - he definitely made this tour and it was the highlight of our honeymoon!
Perfect small towns , chianti region , wine degustation , excellent tour guide . Miniven … not very comfortabl/ seats so so /.
We spent a delightful tour with Kiko who is an incredible tour guide. We visited two beautiful vineyards, had a delicious dinner at a family owned farm, as well as a stop in two special cities along the way. Kiko’s personality, knowledge, and history of the area made this experience outstanding!
This experience was intimate, informative and full of fun, bumpy roads and all. The afternoon/evening flew by very quickly!
Our fabulous guide in addition to being full of knowledge about all aspects of the tour also knew the farm and winery staff and owners and made the trip so personal with lots of friendly chat
