Small-Group Chianti and San Gimignano Sunset Trip from Siena
Recommended by 97% of travelers
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Siena, Italy
- 8 to 9 hours (approx.)
- Mobile ticket
- Offered in: English
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Overview
With no train station and spotty bus service, San Gimignano can be a hassle to reach from Siena. On this small-group tour, sip world-class wine and watch the sunset over Chianti and San Gimignano with stress-free transportation. 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.
- The ease of round-trip transportation from Siena to Chianti and San Gimignano
- A sunset departure to stretch your sightseeing hours into the evening
- Wine tastings and farm dinner are included to avoid hidden costs
- Small-group tour with maximum eight people ensures a 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 DomenicoPiazza S. Domenico, 53100 Siena SI, Italy
Meet under the large tree next to the red brick church
End point
This activity ends back at the meeting point.Start time.2:30 pm
Itinerary
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.
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)
1
Cantinetta di Monteriggioni
30 minutes • Admission Ticket Free
2
Historic Centre of San Gimignano
1 hour • Admission Ticket Free
3
Strada Statale 222 Chiantigiana
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
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Cancellation Policy
You can cancel up to 24 hours in advance of the experience for a full refund.
Traveler Photos
Featured review
Marco was an absolutely amazing tour guide! He was so knowledgeable and personable. The tour was the perfect ending to our time in Siena allowing us to explore neighboring areas. The beauty, views, and wine were perfection! Highly suggest!
Reviews
4.8
based on 67 reviews
Sort by: Most insightful
The highlight of our visit to Tuscany! Our driver William was wonderful. If I could give this tour a 10 I would. I would make sure to ask for William also.
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!
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
Marco was an absolutely amazing tour guide! He was so knowledgeable and personable. The tour was the perfect ending to our time in Siena allowing us to explore neighboring areas. The beauty, views, and wine were perfection! Highly suggest!
We loved the whole experience from the commentary on the history of wine in the Tuscany area by our Tour Guide Danielle to the wine tasing stops. We visited a wine cellar on the winery/ farm used by several generations of the same family.
The dinner served at the end was delicious and the wine was excellent.
This was a wonderful tour - the best we went on in Italy! Our guide was very knowledgeable and friendly, the wine tasting was wonderful, and the dinner was perfect. Highly recommend!
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!
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.
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.
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!
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!
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!!!
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.
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.
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!
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 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 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 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 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 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 knowledgable. Awesome views of the countryside. Winery/dinner was really awesome.
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 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 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 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 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 the region. The farmhouse meal was superb.
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