Afternoon in Siena and Chianti Wine Tour with Dinner from Florence

Firenze, Italy
Likely to Sell Out

From $76.09

Select Date and Travelers

Free cancellation
Up to 24 hours in advance.
  • 7 hours (approx.)
  • Mobile ticket
  • Offered in: English


Experience Siena and the Chianti region on this evening excursion, departing from Florence. Bypass the daytime crowds and arrive in Siena in the late afternoon to explore the Piazza del Campo. From there, visit a Tuscan wine cellar in the famous region of Chianti and enjoy a 4-course meal paired with local wines. After a romantic evening in the Tuscan countryside, return to central Florence.
  • Evening Siena excursion, wine cellar tour, and Chianti dinner
  • Visit the Tuscan city of Siena and enjoy free time to see the sunset
  • Stroll around Piazza del Campo and take photos of Siena Duomo
  • Tour a wine estate at a Tuscan farmhouse in Chianti and learn about the local wine
  • Feast on a 4-course dinner of Tuscan specialties with up to four glasses of wine

What's Included

  • Air-conditioned vehicle
  • Professional tour leader
  • Dinner at a wine estate with wine tasting
  • Free time in Siena
  • Gratuities
  • Hotel pickup and drop-off
  • Admission to Siena Duomo (approx. 7 euros)

Meeting And Pickup

Meeting point

  • Piazzale Montelungo
    Piazzale Montelungo, Firenze FI, Italy

    TOURS & NEWS KIOSK AT PIAZZALE MONTELUNGO BUS TERMINAL Located at 5-10 minutes walking distance from Santa Maria Novella Train Station. Look for our staff wearing a FUCHSIA CIAOFLORENCE JACKET and holding a CIAOFLORENCE CLIPBOARD!

Start time

02:45 PM

End point

This activity ends back at the meeting point.

What To Expect

Your evening excursion will begins in central Florence. Join your guide aboard a comfortable coach and start your journey through the olive groves and green hills of the Tuscan countryside.

Arrive in Siena and enjoy time to explore independently, checking out the central Piazza del Campo or the Duomo, a stunning Gothic cathedral with interior frescoes and alternating stripes of white and black marble.

After watching the sunset, hop back in your coach and head to the region of Chianti, made famous by its ruby-red wine. There, visit one of the area’s prominent wine estates, set amidst a Tuscan farm. Take a guided tour of the cellars and learn about the production and aging process that gives the Chianti blends a world-class flavor.

Then settle into a table in the main farmhouse or, weather permitting, outdoors for a 4-course meal (sample menu can be found below). Pair your dinner with up to four glasses of the estate’s wine, learning about the characteristics of each from your guide as you sip.

After your evening of wining, dining, and sightseeing concludes, you are returned to central Florence in your coach.


1 hour Admission Ticket Free


2 hours Admission Ticket Free

Piazza del Campo

30 minutesAdmission Ticket Free

Duomo di Siena

30 minutesAdmission Ticket Not Included

Chianti Road

2 hours Admission Ticket Free


1 hour Admission Ticket Free

Additional Info

  • Confirmation will be received at time of booking
  • Not wheelchair accessible
  • Please advise any specific dietary requirements at time of booking
  • Stroller accessible
  • Near public transportation
  • Infants must sit on laps
  • Infant seats available
  • English and Spanish are always guaranteed. In order to confirm the excursion in Italian, German, Portuguese or French a minimum of 4 pax is required
  • Most travelers can participate
  • This tour/activity will have a maximum of 30 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.
  • This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
  • This experience requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund.

Traveler Photos

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Featured review
Beautiful way to see Tuscany! Great wine and food and excellent views. Great guide too - very professional and friendly!


174 reviews
Total review count and overall rating based on Viator and Tripadvisor reviews
Reviews by Viator travelers.
Showing 1-10 of 174 reviews
Not worth it
Shekema_B, Jun 2023
Let's start with the tour was late meeting point had to be there at 245pm the bus didn't get there in time. We around in Siena and it was pouring rain we had to walking 10-15 from where the bus parked which we shouldn't have to that was crazy walking in the pouring rain. Then we had to drive it felt like another 1hr to the winery. We didn't get the dinner outside saw no sunset. Oh and there is no tour of the winery or vineyard,just a lady telling you briefly about 3 different wine while they pour a sample in our glass at the table. The food was horrible dry lasagna doesn't even taste like it came from Italy but more so box lasgana,the bread taste like something from olive garden not the normal Italian bread. I have been all through out Italy and by far worst food I had and a waste of money. I would of thought we would get a tour of the vineyard also no picturesque pictures to take. Mad I wasted my money and day to go here. Also the description said this would be 5 hours but we didn't get back til 10pm so from 245pm-10pm
Don't wear the cute shoes.
Rocky_R, Jun 2023
I did not understand what all was involved in this tour. The guide and driver were great. But they take u to Sienna up and down hills and all the way thru town then u ho back and take another drive to the winnery. Up another hill, I thought there would be explanation about what wines go with. The food was basic. I wish they rold u more about thier honey.
Nice evening in Tuscany
Michele_C, May 2023
Nice drive, great amount of time a in Sienna with time to shop. Winery was good, food was okay. Great night in Tuscany!
I really enjoyed walking...
Andrew_S, May 2023
I really enjoyed walking around Siena with the Rick Steves' guidebook. We only had time to briefly stop at all sites on his map and it would've been nice to spend more time at the medieval museums and churches. Plus the weather was a bit rainy. Worth a day or two. Much more low key than the bustle of Florence. Only gently touched by the Renaissance. The wine tasting was very good too. Santiago (driver) and Roberto (guide) were exceptional. Grazie!
We were left by our guide...
michele_m, May 2023
We were left by our guide Stefan’s at the square. Myself and family of six as well as one other person. That was seven people, we met at meetings point then continued to bus Stefan did not turn around once to see we were all following. We were lost and we’re trying to find our way for about 35 mins. Not until we find another guide from another company helped us as we tried to call numerous times to meet up with bus. Very frustrating and unprofessional. Not happy at all with the tour.
Response from Host, May 2023
Dear Customer, We are sorry to read that something went wrong during your tour. Our tour leader Stefano is very experienced and it is very difficult to believe that he left seven people behind. In fact he called us and said that you were not at the meeting point in Siena so we called you several times but the calls went straight to the voicemail. It is right for that reason that it is important that all of the customers leave us a working number. Otherwise, in case of emergency we are not able to reach you. We would also like to highlight that we cannot be held responsible if somebody loses contact with the tour leader. This is something of client’s interest to be on time at the meeting points and to follow the guide especially if you are in a foreign country. We will be glad to welcome you again in the future and let you have a more complete experience around our wonderful Tuscany. Have a nice day, Ciao Florence Staff
No tour for us!
Diane_C, May 2023
I wish we read more of the reviews before we booked this tour. We struggled to find the pickup point, and the tour guide was NOT at all helpful. It turned out that we were a quick 4 minute cab ride from where we needed to be, but he refused to wait for us. Fortunately, our wine tour with another tour guide a couple days later MORE than made up for the money we lost by missing this trip. Read ALL the reviews, and make certain you do a test run to the departure point. Incredibly frustrating experience.
Response from Host, May 2023
Dear Diane, We are sorry to read that you couldn’t find the meeting point. Actually it is centrally located, just behind the Santa Maria Novella train station. We called you several times but you were way too far. We waited the most we could but then we really needed to leave; it would have been so disrespectful to those who were there on time. We are sure that if you could have joined our tour, you would have been more than happy to participate. Siena is very charming, especially at sunset when the orange sun shines over the mediaeval town and creates a magical atmosphere. Then, the dinner in the winery surrounded by vineyards and hills, is something memorable. We really hope you can join us in the future to explore Siena and its surrounding. Have a nice day, Ciao Florence Staff
Amazing & Beautiful tour
Nicole_S, Apr 2023
Wonderful tour with great food and wine. We even ordered some to bring home. This was a highlight of our trip.
gina_s, Nov 2022
DO NOT BOOK THIS TOUR!!!!! DO NOT BOOK ANY TOURS WITH CAIOFLORENCE. They are the most unprofessional tour operator I have ever had the displeasure of dealing with. They gave our group of 4 the incorrect meeting point directions and after being in constant contact w them trying to find the meeting point for our Siena sunset tour, stating they are waiting for us- they left w/out us. No refund, no voucher for another time. I have all the communication that transpired, and the result was nil. They were unapologetic and refused any kind of resolution. THE WORST. And to add insult to injury, I submitted a claim through Viator and was denied.
Response from Host, Nov 2022
Dear Gina, We feel extremely sorry to read these words of disappointment from you. We consider this review to be offensive and unfair especially because you never joined our tour and we did our very best to help you. We totally understand how frustrating it could have been and that’s why our staff has tried to help you in every way possible. As you have expressed an opinion that we feel like it does not represent us, we’d like to give our side of the story. On October 29th you were supposed to join our Sunset in Siena tour. The morning of the tour you called us and told us that only two of your party of four people would have joined the activity, as your daughter was not feeling well. Our response was that, as per our cancellation policy, we could not proceed with a partial refund but that we were glad you had advised us, so we could modify the reservation. You then called us at 2.04pm to inform us that all participants were going to attend our tour so we proceeded to update our system again. I was the person who was at the meeting point for the check in and, as there were other tours leaving earlier, I was at the meeting point (with another colleague of mine) from 1.45pm to 3.00pm. As usual, I was wearing a fuchsia vest in order for customers to recognize me. You called our office at 2.44pm (the tour was supposed to leave at 2.45pm) screaming at us that you could not find the meeting location. My colleague proceeded to explain to you how to get to the meeting point and sent you the Google Maps link with the location. The office then called me at the meeting point and told me to wait for a few minutes more, as you said you were close, exactly "five minutes away". The tour was ready to go, as everybody was already on board and had arrived early at the meeting point, but it did not leave, as we decided to wait some minutes more. As I was waiting, I walked around the location looking for you calling your name but never met you. The tour left at 2.55pm with everybody on board, starting to ask us why we would not leave on time. Some customers told us that it did not seem fair to delay their experience to wait for someone who was late. We understand that it could have been annoying for them but we really wanted you to join our tour, so that's why we waited for more. Also, the reason we could not wait for infinite time/come back and pick you up (as you suggested, yelling at one of my colleagues) is that we have a schedule to respect (time in Siena and dinner reservation at the winery) and we want to guarantee our customers the best service. We are sure that if you were on the bus already since 2.30 and, after the departure we would have gone back to the meeting point to pick up other customers, you would have not liked that and would have complained about it. You treated us with disrespect, accused us to be "unprofessional" and held us responsible for losing your tour. You accused us of sending you the wrong directions to the meeting location, while we have all of the proof that we did send you everything correctly. We invite you to please reconsider your opinion on us and try to analyze all of the aspects that are “behind the scenes”of the reason why we “left you”.
Not worth the money
Erlin_E, Oct 2022
If you are looking for a real wine tour, don't join this. Worst wine tour experience ever. Small winery with very normal meal, totally different from expectation. One good thing is the guide is very helpful
Response from Host, Oct 2022
Dear Erlin, we are very sorry to read that this tour didn't meet your expectations. This tour is not just a wine tour, it also offers the chance to visit Siena and stroll into the ancient town under the sunset light. After that, there is the visit of the winery where the wine tasting will be combined with the proposed typical dishes. According to your review, we believe you could have enjoyed more our Chianti tour that includes the visit of two different wineries and vineyards with the whole explanation about the production of the famous wines. I hope you will join this tour during your next trip to Italy, we will be here waiting for you! Have a great day. CiaoFlorence Staff
Description of tour didn't match our experience
Tess_M, Oct 2022
The visit to Siena is wonderful, albeit short. What an incredible medieval town. Be sure to visit the Cathedral, you won't be sorry. The reason for my low rating is the "sunset" wine tour in Chianti. It's mid-October, so the sun sets earlier, but the tour company didn't take that into consideration. By the time we got to Chianti, it was dark and we couldn't see anything. I agree with the other reviewer who suggested that they rename the tour for the late fall and winter months, or change the time of the tour to actually see the sunset and some daylight. Also, the people at the winery are lovely, but the food was not very good at all, and it's served on paper plates. Finally, the line in the event description that says it's "up to 4 glasses of wine" is misleading. We received 4 "splashes" of wine throughout dinner, maybe adding up to a full glass in total. With so many wine tours available, I'd find another one and take a pass on this one.
Nice trip and dinner; no sunset
sophia_S, Oct 2022
Great tour overall. Had good time exploring sienna. The dinner and wine is delicious. The tour guide Filippa and the driver are great. I was hoping to see the sunset while having dinner; but it was totally dark when we got to winery (see attached pictures). Can’t even see the wine yard.
Don’t waste your money!!
Amber_G, Oct 2022
To start with the positives, the trip to Siena was lovely although this was ‘free time’ and we could have had the same experience if we had arranged to take our own transport to Siena. Then came the ‘wine estate’… we took the bus there at 6pm and so we saw no sunset, fine, it’s October, but perhaps consider renaming the experience for the winter months. When we arrived at the estate it was pitch black and so there was no opportunity for photos or exploring the vineyards. We were then rushed through into a small wine cellar for a 5 minute talk in which i didn’t learn anything. We were then taken upstairs for dinner. Two slices of ham, a crumb of cheese and some stale bread served on a polystyrene plate came first. Then a lasagne which was nice enough but nothing special. Then a pork dish with some sort of butter bean and gravy concoction. It wasn’t clear if it was supposed to be served cold or hot, but let’s just say it left much to be desired and was stone cold. The tiramisu was also ok but nothing special. You might think the wine was a saving grace… you’d be sorely mistaken. We were given a splash of each to go alongside each of the four courses. The description of up to four glasses of wine was a gross overstatement, I don’t think we would have been able to make up one glass if you’d combined the pathetic portions. I know it was a tasting but come on!! The owners of the estate opened 6 bottles of Prosecco, but made two bottles stretch across the whole group of around 30 people. The owners then drank the remainder themselves whilst standing around in front of us. The whole thing was essentially a mass marketing pitch for us to buy their wines downstairs in their shop. Please save your money and DO NOT book this tour. Everyone on our table was so disappointed.
Response from Host, Nov 2022
Dear Amber, thank you so much for taking your time to leave us a feedback. This is a package that allows people not only to visit Siena but also to enjoy a typical dinner while tasting the famous Chianti wine. You reached Siena with an experienced tour leader that gave you all the information about the town providing interesting tips and suggestions about how to spend your free time there at best. In this period of the year, the sun sets down earlier but at some point you see the sunset and, as per the title, you will be able to see it in Siena, not while you dine. We carrefully select our restaurants so we are very sorry to read that something went wrong. We will forward your comment to them as to improve the service. Anyways, this is a wine tasting, we don't want to let people get drunk during our experiences. We offer the chance to taste the famous wine and, if you like it, the owners of the wieries will be glad to sell their bottles. Please, note that they are producers other then owners, so they are very proud of their products and they have a big interest in selling them and are happy if you like them. We thank you again for sharing your thoughts and we hope you can join us again for your next trip in Italy. Have a lovely day, CiaoFlorence Staff
The wine tour was my...
Karen_A, Oct 2022
The wine tour was my favorite part of my entire trip to Italy. The food and the wine were spectacular. The only downside was that we missed the sunset due to traffic but it was an amazing experience.
Disappointing trip
Elizabeth_T, Oct 2022
I would like a call about this excursion. I was very disappointed about a few things and was nothing like the description I read and was expecting.
Response from Host, Oct 2022
Dear Elizabeth, we are very sorry to read that our tour didn't meet your expectations. This is a great tour that allows people to spend some free time in Siena and watch the amazing sunset when the Medieval town is coloroured in orange by the light. After admiring this natural spectacle, the staff of a typical winery in the middle of the Chianti countryside will be waiting for you for the dinner and the wine tasting. We do really care about our clients' reviews so it would be really appreciate if you send us an email saying what you didn't like so we will do the most we can to improve our service. Have a lovely day, CiaoFlorence staff
What Sunset!!!!!!
Claire_R, Oct 2022
Unfortunately I have to give this tour only two stars……this is only because it is described as a “Sunset Siena tour”….that’s great if you are experiencing the tour between the “high” season. However, we went on the tour on the 11th of October and who knew that the sun sets before 6.30pm European time in Autumn………and we left Siena by bus through streets & Motorway at 6.30pm totally missing ANY sunset…….we arrived at our host Vinyard for a sunset dinner in complete darkness……not quite a Sunset tour! I will say that our tour guide was very Knowledgeable, and our driver very competent. The visit to Siena was very enjoyable, and also the visit to the vineyard where we were served a very enjoyable meal with a very good wine tasting. But, the tour really needs to be adapted to the seasons, there is no point in a sunset tour, when you cannot see the sunset at all! …….and it was a very clear day in regards to weather.
Vera was an excellent...
Laura_C, Oct 2022
Vera was an excellent guide! We overestimated our walking abilities. We are in our mid to late seventies. The downhill is harder on old knees than uphill.
Super fun but not quite what it said on the description
Alyssia_A, Oct 2022
Vera (our guide) was absolutely lovely This experience is essentially just transport to Siena from Florence, and then a tasting course at a farm. The glasses of wine are not full glasses of wine but rather about an inch but this wasn't unexpected - you had 4 of them The food given was cheese, meat, lasagne, beans, tiramasu, oil The sunset happened whilst we were on the bus, but you do the tasting inside the house anyway so this doesn't really affect that too much You don't get a wine tour around a vineyard, but go and look at their wine cellar We had a great time but it is definitely not quite what we were expecting
Not the sunset we expected!
David_C, Oct 2022
We appreciated the guide and the driver, but the management of the timing and the actual sunset on that day of 7:03pm was atrocious, as we had arrived at the winery 30 mins post sunset. The expectation from the tour description was sunset at the winery and sitting outside for dinner - this was not the case and the sentiment was felt from everyone on the tour we spoke with. The tour should have shortened the time in Siena to ensure we arrived at the winery as expected. This also should have been obvious with the wind and cool temperatures in Siena as further reasons to have departed earlier. And a short stop on the way there to take a few pics of Montereggiano would have been a better use of time and, after the descriptions offered by the tour guide, should have been more than a brief sighting as we drove by. We have taken a number of Viator offerings and this was a disappointing one!
Great time in Sienna
Randy_G, Oct 2022
The drive was beautiful and exilerating. The tour was educational and the wine tasting was fun. Best part was meeting new friends at the dinner table. Vera our guide was excellent and kept the group under control
disappointing wine trip and meal
IAN_L, Oct 2022
it was a rainy day which was unfortunate and kind off washed out the Siena experience and the sunset. This of course is nothing to do with the operators. The guide and driver were excellent. However we found the actual wine tasting and meal very disappointing, it was described as wine tasting and a four course meal. Four course taster would be more accurate. It was not as we had imagined it to be. Would not repeat the experience
Wine tasting at its best
Harshvardhan_S, Oct 2022
Smooth experience and amazing wine. Loved the vegetarian food that was made specifically for us. Loved the ride through the Tuscany countryside.
Disappointing experience
Grant_K, Sep 2022
The best part of the tour took place at the winery. Members of the family that own the winery were both friendly and knowledgeable about wine and the history of their farm. The dinner including the wine was very good and we purchased both wine and olive oil produced by the winery. The tour guide and the rest of the tour was so-so. The tour guide did not provide much commentary or history about the countryside as we drove to the different locations of the tour. We were dropped off at Siena for approximately an hour to wander around on our own with little recommendations on what to do there. More effort needed to be provided to entertain and educate the participants.
Joseph_C, Sep 2022
San Appiano sunset after our Siena tour was wonderful. We had a toeential downpour in Siena but still enjoyed the experience of being there. Our hostess Phillipa was WONDERDUL as was our driver Franco , and Roxanna our hostess at the winery was both knowledgeable and engaging. Our food accommodations for being vegetarian had everyone else jealous! Thank you for a great tour
Response from Host, Oct 2022
Dear Joseph, Thank you for your pleasant review. We hope this tour made you feel special! We are very happy to read that you enjoyed the guides and hostess, we take pride in the people we work with. We hope to see you again soon on one of our tours!
You will regret not doing this
Ethan_W, Sep 2022
Incredible experience, my favorite tour so far! Sienna was breath taking and our wine/food tasting was very good. There was about 20 strangers in our group and by the time it was over, there was 20 friends. Arrive early! I was 6 minutes late to the start time and almost missed it!! Florence traffic is no joke.
Response from Host, Oct 2022
Dear Ethan, What a wonderful review, thank you very much for sharing it! We hope you will keep this tour engraved in your memories forever. We hope to welcome you again soon!
First trip to Florence
courtney, Sep 2022
The 2 hour visit to Siena was great. The view of the vineyard was spectacular and the wine tasting and dinner were wonderful.
Not great
Adriana_T, Sep 2022
This started out bad and got worse. They knowingly had used a bus that did not have the air conditioning working and we had to wait an hour to get a working bus on the side of the road. We were supposed to witness the sunset at the winery and completely missed it. Had to see it from the bus. Siena is a beautiful town and the wine and food was ok. I definitely will be asking for a refund for a poorly executed tour.
Siena, dinner and wine tasting
William_L, Sep 2022
Approximately 2 hour free time to explore in Siena and then onto Saint Appiano winery for dinner and wine tasting. Combined English and Spanish tour was a little distracting, but Serviano did a great job as our guide and Roberto safely drove us around. Beautiful Tuscany countryside views !
The most beautiful sunset
Syeda_R, Sep 2022
This was a very wonderful experience. We got to tour Siena on our own and was taken to a wonderful Chianti wine yard owned by a family. If you’re expecting a Michelin star meal, you won’t get it, but I thought the meal and the wine were suitable for the price I paid. Do it! It’s a good excursion from Florence
Great trip to beautiful Siena
Jennifer_P, Sep 2022
Siena is beautiful, well worth a visit. The cathedral is very impressive. Wine tasting and dinner topped the day off, very much recommend this trip
Beautiful tour of Siena and Tuscany winery
Angela_S, Aug 2022
Great trip with our tour guide, sweet and funny Giordano, and driver, Antonio to beautiful Siena where we were able to roam two hours on our own. Perfect amount of time to experience Siena, its’ Duomo and local life. Very comfortable van bus with air-conditioning. Loved visiting the family owned winery where we had an amazing dinner and tour. Barbara and her mother were fantastic hosts. It was great to be able to order their wine which they ship direct around the world.

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