Small-Group Chianti and San Gimignano Sunset Trip from Siena

Badge of ExcellenceSiena, Italy
Small Group Chianti and San Gimignano Sunset Trip from Siena
  • 8 to 9 hours
  • Mobile ticket
  • Offered 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, 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

What's Included

  • Professional Guide
  • Transport by air-conditioned minivan
  • Tour of winery with wine tasting
  • Traditional dinner at farm
  • Gratuities
  • Hotel pickup and drop-off
  • Entrance fees to attractions in San Gimignano

Meeting And Pickup

Meeting point

  • Piazza San Domenico
    Piazza S. Domenico, 53100 Siena SI, Italy

    Meet under the large tree next to the red brick church

Start time

02:30 PM

End point

This activity ends back at the meeting point.

What To Expect

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.

Basilica Cateriniana Di S. Domenico (Pass By)

Cantinetta di Monteriggioni - Montechiaro Organic Wine Experience

30 minutesAdmission Ticket Free

Historic Centre of San Gimignano

1 hour Admission Ticket Free

Chianti Road

2 hours Admission Ticket Included

Additional Info

  • 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

Cancellation Policy

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.

Traveler Photos

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Featured review
We really enjoyed Tuscan Escapes' Sunset trip from Siena. We became part of a fun group of eight from Alabama, California, and Iowa. The wine tasting was delightful and it was so nice visiting San Gimignano later in the day. The dinner in Chianti, at a farmhouse/winery, was delicious. Our trip was made even better by our oustanding guide, Mattia. He is very knowledgeable about wine, humorous and informative. We highly recommend this tour!


50 reviews
Total review count and overall rating based on Viator and Tripadvisor reviews
Reviews by Viator travelers.
Showing 1-10 of 50 reviews
Wonderful Afternoon/Evening Trip from Siena to San Gimignano and Chianti
Sue_E, Nov 2023
We really enjoyed Tuscan Escapes' Sunset trip from Siena. We became part of a fun group of eight from Alabama, California, and Iowa. The wine tasting was delightful and it was so nice visiting San Gimignano later in the day. The dinner in Chianti, at a farmhouse/winery, was delicious. Our trip was made even better by our oustanding guide, Mattia. He is very knowledgeable about wine, humorous and informative. We highly recommend this tour!
Fantastic small group sunset tour from Siena
Marianne_G, May 2023
We were picked up on time at the location outside the Basilica Cateriniana San Domenico in a very comfortable minivan with a total of 6 passengers on our sunset trip. Georga was our wonderful guide for the afternoon/evening. She was very informative, upbeat and a great driver. The tour was well paced with stops at viewpoints of the beautiful Tuscan countryside as well as visits to the towns of San Gimignano & Monteriggioni. We had a wine tasting at small, family run organic winery that also produced Olive Oil and Saffron. Dinner was at a great little family farm and was delicious, made with local ingredients! Highly recommend this tour with Tuscan Escapes.
Restaurant dinner
Marlene_H, Apr 2023
I was disappointed in the trip. The tour guide, William, did the best he could. He made a special stop so we could all get good pictures of San Gimiginano. The dinner at the end was billed as a dinner on a farm. It should have been billed as dinner in a restaurant that is on a farm. Two different atmospheres. One more intimate and the other more ordinary. The restaurant was full, including a noisy party in the banquet room next to our table. The restaurant wouldn't close the doors at first which made having a conversation very difficult. The wine tasting was done in a small setting and was very nice.
Best of everything Tuscany!!
Sharon_M, Apr 2023
Our tour guide (Jecko?) was amazing as was our small group tour!! The short stop was just long enough to get a good flavor of San Gimignano and fry a gelato fix, then on to the family owned winery tour which was exceptional! Lots of wines to taste with great stories connected with wine names etc. great cheeses, meats and breads to accompany the tastings. Lovely family! On to the sunset dinner at a wonderful “farm” out in the beautiful Tuscan countryside. This was the most amazingly delicious farm to table food and 5 courses we’ve ever had! Fresh fava beans to start ( with a nice Chianti!) and many wines to try with each course. Best tour of our trip. We started and ended in Siena and returned rather late ( 10:30) and walked the streets a mile and a half back to our villa, but felt quite safe and good to walk off full stomach. No taxis that we saw so just headed back using Google maps! Highlight of our first trip to Italy!
Fun tour with wine and history
Stacy_H, Jan 2023
This tour was amazing! Our guide Guillermo or “Bill” was fantastic! He helped make sure we were parked in the right place, told us about the history on the drive but kept it fun and exciting. The wine stops were great. Perfect allotment of time for the stops in San Gimignano and Monteriggioni. The dinner was phenomenal and the wine with dinner was even better! We definitely recommend this tour. It was a great way to see the cities, learn about the history and have some food and wine too!
Stunning views and fabulous dinner
Dawn_H, Oct 2022
WOW!!! We relished the stunning views everywhere you looked! We caught the sunset while walking around San Gimignano and then had a lovely meal at Montemorli farm! Fabulous!!!
Lovely Afternoon and Evening
mnomentana, 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.
Janet_B, 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!
Hilary_P, 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!
Great Trip
Kenny_B, 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...
Peter_M, 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...
John_E, 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...
Nancy_S, 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...
S_N, 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.

From $198.43

up to 24 hours before the experience starts (local time)

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