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Small-Group Chianti and San Gimignano Sunset Trip from Siena

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Siena, Italy
Small-Group Chianti and San Gimignano Sunset Trip from Siena
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icon8 to 9 hours  (approx.)
Mobile ticket
iconOffered in: English
Good for avoiding crowds

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Sip world-class wine and watch the sunset on this day trip to Chianti and San Gimignano from Siena. Led by an expert guide, explore the medieval town of Monteriggioni and visit Chianti wineries for tastings. 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 for eight people to keep the experience as intimate as possible. 
  • Sunset trip to San Gimignano from Siena
  • 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 with wine
  • Small-group tour with a maximum of eight people ensures a more personalized experience
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Professional Guide
Transport by air-conditioned minivan
Tour of winery with wine tasting
Traditional dinner at farm
Hotel pickup and drop-off
Entrance fees to attractions in San Gimignano
Piazza San Domenico , Piazza S. Domenico, 53100 Siena SI, Italy

Meet under the large tree next to the red brick church

2:30 PM
This activity will end right where it started.
Hop aboard your luxury coach in Siena and begin the journey 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 the town of Monteriggioni, where you 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.
Pass By:  
Basilica Cateriniana Di S. Domenico
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.
Stop At:  
Cantinetta di Monteriggioni
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.
Duration: 30 minutes
Admission Ticket Free
Stop At:  
Historic Centre of San Gimignano
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.
Duration: 1 hour 
Admission Ticket Free
Stop At:  
Chianti Road
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.
Duration: 2 hours 
Admission Ticket Included
  • Confirmation will be received at time of booking, unless booked within 1 day of travel. In this case confirmation will be received as soon as possible, subject to availability
  • Customers who have not reached Italy's legal drinking age of 18 will not be served alcohol
  • Not wheelchair accessible
  • Stroller accessible
  • Near public transportation
  • Infant seats available
  • No heart problems or other serious medical conditions
  • Most travelers can participate
  • This tour/activity will have a maximum of 8 travelers
  • OPERATED BY Tuscan Escapes by Papilio SRL
You can cancel up to 24 hours in advance of the experience for a full refund.
  • For a full refund, you must cancel at least 24 hours before the experience’s start time.
  • If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the experience’s start time will not be accepted.
  • Cut-off times are based on the experience’s local time.

Learn more about cancellations.

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30 Reviews
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Showing 1-10 of 30 reviews
Lovely Afternoon and Evening
, Aug 2022
Our guide was lovely She spent a lot of time giving us the history of Siena and the surrounding cities. We really enjoyed the Tuscan countryside, wine tastings and the dinner on the family farm.
, Jul 2022
Thoroughly enjoyed our tour and the small group experience. Our guide, Mattia, was personable and very knowledgeable. He expertly educated the group on wine making in Tuscany as he drove us about. The stops were perfect in length with a special photo op before entering the town. Wine tastings were both superb and the dinner outside delicious, made better by conversation with the group.
Perfect trip!
, May 2022
The tour was incredible, and our guide Elio was warm, funny, and very informative. He tailored the information to the group’s interests, made sure everyone was enjoying themselves, and was an awesome driver (those roads are no joke!). Our dinner was homemade and beyond delicious (saffron gelato was a surprising delight). Highly recommend!
1 traveler found this review helpful
Great Trip
, Sep 2019
From the moment David (Michelangelo) picked us up this was one of those days you didn’t want to end. We were a party of four enhanced with another couple who helped make a really enjoyable experience. David’s knowledge and advice was both informative and enjoyable. Time enough was given to our various visits before arriving at Le Masse for our wine tastings where Christina’s enthusiasm for her vineyard was so obvious. The meal we had at Poggio Alloro as the sun set and the lights of San Gimignano came on was beyond expectations. Food and drink were of quality and plentiful. Highly recommend this trip and David’s guidance.
Enjoyed the tour quite a bit, but...
, 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.
We loved this tour especially since...
Robert S
, 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!
This tour was worth the price. Elena...
Annette P
, 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.
Five star all the way!! These tour...
Constance E
, 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.
First the good: The...
Tony B
, 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.
Great tour guide - very friendly and...
, Jun 2014
Great tour guide - very friendly and knowledgable. Awesome views of the countryside. Winery/dinner was really awesome.
We never saw the sunset which is why...
, 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.
We enjoyed this tour very much, wine...
, Sep 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.
The tour was wondrful. Daniel and...
Laura I
, May 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.
A great way to see the Tuscan...
anne c
, Nov 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.
We were a group of four gals and our...
Veronica T
, Nov 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
The guide was full of knowledge about...
Larry D
, Oct 2012
The guide was full of knowledge about the region. The farmhouse meal was superb.
Amazing! Rain and all our guide...
Gale O
, Sep 2012
Amazing! Rain and all our guide Made the outing enjoyable. I will take this tour again next year with my friend.

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