San Gimignano, Chianti, And Montalcino Day Trip From Siena

Our tour was canceled 2 days before the tour date by the vendor. I am so disappointed that I did not get to go to San Gimignano!!! It was replaced with a trip that we were told would be similar. We were very unhappy with the replacement tour. It was a large bus full of people, not a small group tour that we were looking forward too. The guide had to interpret everything into English, Spanish and Italian. While I am amazed at her skill, I believe we received less historical information because everything had to be translated into 3 languages. We signed up for this tour months in advance and now we didn’t get to see San Gimignano. We are very disappointed.

The company will cancel with very short notice and without giving a reason. (“Technical difficulties”). So don’t count on them for your trip planning. I presume that the true reason for the cancellation was because there weren’t enough people signed up to make it a full tour group. Still very disappointing to have so little notice and have to come up with a replacement itinerary. My credit card was charged none the less, as they presumed we would accept an offered alternative tour, which we did not want. After a day and a few emails, the charge was reversed. The experience has left a bad impression of Viator for me.

Wonderful , exceptional experience in Tuscany’s world renowned wine towns. Immersive and comprehensive.

The experience was great. We had the chance to visit multiple towns out in the countryside of Italy near Sienna/Tuscany. Offered exquisite glasses of wine, a lunch, and visited iconic landmarks along the way. Huge shout-out to our tour guide Bianca for making the journey fantastic and an unforgettable experience.

Nicely organized tour, great food and wine. San Gimignano is beautiful but packed with tourists (including myself too) during mid day. Would love to visit it during some quieter time if any.

Our guide Luca was very knowledgeable and gave great information all day throughout the tour. He had good recommendations for restaurants in the cities we visited, and explained the different wines and products very well. The tour itself was nice, with visits to two wineries and some cities with impressive views over the hillside in Tuscany.

Buyer Beware. This tour was a 3rd party vendor My tour 366, who rescheduled the tour and overbooked what was supposed to be an 8-12 semi-private tour to 28 people. The two wineries were not able to accommodate. we ended up in the production area at the last minute, not the tasting room. The bus driver initially pulled into a lovely winery only to back out and take us to another venue twice. The 1st venue clearly was not expecting us and was trying to set up last minute. we could not use the main restroom because there was another tour and we were ushered into some dirty back room bathroom. We were served bread which was moldy. The second tour same thing we pulled into a beautiful estate, only to back out and end up on a small production farm, they were actually working the harvest and it appeared we were fit in last moment. The wine maker came out and poured wine and asked people to come help him. The area we were sent to looked to be where the staff had their breaks. There was supposed to be a tasting for olive oil/balsamic vinegar, that did not happen. our guide when asked said, these things happen it is the busy season, well it is October and not peak season. Not for $668 for 4 people. Such a disappointment. you hear how wonderful Tuscany is, it was our 40th wedding anniversary, and a once-in-a-lifetime trip. I am not by any means a wine snob, but have been to some pretty nice wineries in Napa and Sonoma so I know what to expect. This was not even close. We booked with Viator because of their reputation. Our guide lied to the tour company and said everyone was happy. I have so many photos that I will be sharing on Social media so noone else wastes their money and time. Keep looking if you want that fabulous once in a lifetime Tuscany experience you dreamed of, this is not it

Below are the details of our booking: San Gimignano, Chianti, and Montalcino Day Trip from Siena Guided tour Date & time Mon, Oct 13, 2025 • 08:30 AM Language English - Guide Booking ref. 1324690867 Travellers Joan Wright • 2 adults Activity provider myTour in Italy Powered by Ticket barcode 1324690867 Although this tour was not planned in our budget, we decided to book the 11 hour tour. At a cost of nearly $250 each, AUD, we had hoped to have value for our money. We were very disappointed on many levels. We tried to write a more detailed review, but the restriction of the max number of characters, did not allow for this. Therefore we will continue here. We were not impressed with the guide who talked incessantly with the driver, who was driving with one hand and turning his head constantly towards the guide. We found this stressful and didn't feel comfortable or safe. Also, we thought just being left to our own devices to look around San Gimignano without a guide was not what we expected having been on similar tours before at this level. The first winery was interesting as they seemed not to be expecting us. We were disappointed that we were served only bread soaked in olive oil! The trip to the 2nd winery was very long and we heard from fellow participants that it was not the winery we had been promised. Again the only food for this expensive tour was bread and olive oil! The stop off at Montalcino was disappointing as most shops were closed at that time of day. Then to travel back in the dark was not a good ending to our day. Fellow travellers felt the same.

The tour was a great opportunity to see some beautiful places in Tuscany. However was a bit disappointed with no cheese and salami as stated on the tour at the wine tastings. But overall the experience of two wine tastings at two beautiful vineyards was amazing. I always dreamed of being able to sit in the vineyards sipping on the delicious wines and it came true. The hosts at the vineyards were amazing and it was good to learn how they make the wines. I do recommend although would prefer to spend more time at the vineyards

The first wine tasting did not take place in a winery. The place we have been WAS NOT A WINERY, they did not expect us, it was dirty inside out and looked more as a trap. Further, in Montalcino we stayed too little, because we spent too much time in the trap. In the last wine tasting, which took place in a real beautiful winery, we arrived almost at their closure.

Misrepresentation of the tour! No guide, just a driver, who doesn't speak a word of English... We could drive there ourselves

Wonderful trip with a great tour guide Veleaka. This was an 11hr tour and we were never bored. It was a leisurely trip with the best views of Tuscany we saw while in Italy.

We enjoyed our day tour to the vineyards and the rides of Tuscany region !!! Highly recommended this tour if you have a few days to Siena or just one day to spare from Florence.

First winery was nice though it was an extra $20 for lunch which was very confusing. Tour guide wasn’t friendly and slept a lot. Second winery was horrible.

The country side was beautiful and the two wineries were amazing and different. There were some mix ups in our visits and timing but our tour guide handled it well. Highly recommend this tour

Lovely day and easy itinerary - starts early but it's for the best - starting in san Gimignano before crowds arrive, then moving on to a great winery - lunch is an option there, unless you're bringing food or buy something to go in san Gimignano, this is really the only lunch option so I recommend it. The tour itself is a nice mixture of walking and wine interspersed so you never feel overly tired. Vincenzo was an excellent guide and really added a lot of history to what we saw. Great day overall highly recommend

I was really excited to take this tour. San Gim and Montalcino are two of my favorite towns, and I love Vernaccia & Brunello wines. First, the Sprinter a/c didn't work. The van was stuffy and hot, and this was early May. Second, our tour guide was checked out. She didn't seem to want to be there. There was no explanation of where we were going, no history, no enthusiasm. The first winery was a disappointment. It was very industrial. Not the Tuscan experience you want when you go to Italy. The wines were good, and the sommelier did a good job. Lunch was rigatoni with a meat sauce for €20. It was o ovecooked and so salty no one ate it. The 2nd winery was more of what I had hoped. The sommelier did a great job, but the wines were not very good. I actually felt sorry for him. On the plus side, we met some nice people, and any day in Tuscany is a good day. I do not recommend this tour.

Our driver was so friendly and knowledgeable about the region. The itinerary was put together so well giving us time to explore yet keeping us moving along to view four towns. Starting in San Gimignano, moving onto the winery in Chianti for our first tasting with lunch. We learned a lot about the wine and the region. We shared a Great experience with one other couple who we just met that day.

We had a wonderful time touring Chiani and Brunello regions. Vincento was very knowledgeable and even stopped for photos. Luxury van made for a very nice ride. Plenty of time to tour San Gimignano.

Great wine tasting experiences, guide Mikaelo was very knowledgeable with history and culture of the area. My only disappointment was that we were dropped off for the towns & our guide didn’t go with us. For the cost of the tour we purchased, I was surprised. I do very much appreciate him taking us on as a tour at the last minute as our previous tour cancelled.

Our driver, Giovanni, was prompt and provided a clean vehicle but he was NOT a guide as the trip was advertised. Rather than talk about Italy, he wanted to engage about politics and his heavy smoking between stops made the van stink. Our tour left at 8:30 to get to San Gimignano. We were disappointed to arrive in the town to see nothing open. We had until 11:30 to wander but it was frustrating not to be able to go into any shops or climb the tower until 10:30 or 11. It felt like an hour and a half of wasted time. We were traveling in January, so perhaps the time of year was a factor but the company should adjust the times. We stopped for a fantastic wine experience at a Chianti winery. Leda was wonderful and it was a highlight. We also enjoyed the winery at Montalcino, but it was a lot of wine in a short time. Our final stop was a town visit in Montalcino. By now it was dark and stores and attractions were closed again. This would have been a much better trip if there was more time in the towns while things were open.

Enjoyed the tour. Vincenzo was a charm … thank you for the intriduction to driving in Italy! Plenty of wine 🍷 Good company in group too.

Having a driver made it easy to explore these Tuscan towns. The meeting point was easy to find. You couldn’t called this trip a “guided tour” the driver gives you some information as they drive you around but they don’t accompany you in the town. Felt like we missed some of the detail you’d expect on a tour like this.

Our driver was very helpful and his driving was good. Had a great time even in very heavy rain. Wine tastings with lunch were great.

I signed up to enjoy a day up in the three 3 towns with my wife. Unfortunately, the day before the schedule we were told that the trip had been cancelled! Subsequently we were offered an alternative, instead of 3 towns and 9 hours out there the new offer included only one town Montalcino and instead of leaving at 8:30 we left at 2:00. I paid about $250.00 for the trip so I believe we were due a refund of at least 50%, if not more of what we paid. Unfortunately they just told me there will be a total of $40.00 refund which is totally unacceptable. I believe this is clearly a set yo to take advantage if tourists and I demand that we get appropriate reimbursement. Please let me know about your desicion. O plan yo escalate this to the credit card company if it is not quickly taken care off for us. Thank you for your attention..

This trip was advertised by Viator as including a guided host and multilingual escorts outs. Neither of these services were provided. Several of the travellers in our group attempted to contact the tour operator as the driver was late. They did not respond. The other minivan with 8 travellers were picked up on time, the driver/guide spoke English and the travellers told us he was excellent. Our driver spoke no English, stated he does not speak English and remained silent throughout the trip. He merely dropped us off in San Gimignano in a torrential storm with lightning where he had to hide out in the only one open shop early in the morning and wait for the driver’s return in 2 hours.

We booked an English guided tour and received none of what Viator advertised. No guide, and the driver could not speak a word of English. I actually feel bad for the driver. After showing up late, he took us to our first destination and simply dropped us off and pointed in the direction we were supposed to walk. It took a few minutes of hand gestures to figure out when he wanted us back to the van. We immediately contacted Viator in the hopes of resolving the issue. But to our surprise, Viator said they were unable to get any response from the local company that they were using. They did however confirm that we were not receiving what we paid for. It was a small group tour that cost just over $400 per couple. All three couples on the tour complained mid tour. And we all received the exact same response. “Sorry, you are right that you were supposed to have an English guide. Sorry. We will give you a $40 return. Can we help with any other tours?” Seriously. 10% return for a tour that delivered nothing of what was advertised and then they had the nerve to try and sell us another tour. On a somewhat humorous side. All three couples received the exact same response. Almost as if it was pre programmed. We’ve held off on this review to give Viator time to make good on their product. They asked us to wait three days. It’s now day four and still radio silence. In an attempt to help others avoid this one at all costs. Don’t get taken for a ride. And if Viator reads this, it’s not too late to rectify the situation.

It wasn’t anything as advertised! We booked an English guided tour and no one had the ability to speak a single word of English. We were dumped at locations where the driver (who couldn’t speak a word of English) just pointed us in the direction to walk. We immediately contacted Viator at our first stop who confirmed we weren’t getting what we paid for but said their local representative was unresponsive to them. All the parties on our tour complained and we received a pathetic 10% discount which we declined. We have held off on this review to give Viator time to rectify the situation but having waited the time they told us to wait and having heard nothing we now feel it’s our duty to warn others so you’re not taken for a ride. Avoid this “tour” at all costs! We have taken other Viator tours that have been good but this was a total ripoff and they are not standing behind their product.

Montalcino was not worth a stop. Brunello wine was good but host’s English was not good enough. The stop at Poggio Al Laghi Was good. Driver was very nice and accommodating.

Giovanni was great as a guide and driver. Air-conditioning in the van was brilliant. Beautiful places to see. The highlight was Poggio al Laghi winery with lunch. Brilliant! Very long day but worth it. Loved it

Giovanni was great as he was filling in for someone on this day. The visit to San Gimignano was lovely. But the highlight for us was the winery lunch at Poggio al Laghi! Local food and delicious (no sulphites!!) Wines. I wish I could ship a whole crate to Australia! It was a long drive to Montalcino and the second winery I think we all agreed we could have done without as it was a very long day. 11 hours all up! But we still loved it was a great experience. Air-conditioned van was great! Thanks Giovanni!

We were all on time, but the company hadn’t told the driver the list of passengers, took some time to communicate it, chewing time out of our tour. The tour is run by a driver not a tour guide, so do your own research on history beforehand. Office was uncontactable by phone or message. Driver was personable enough, but just doing a job. San Gimignano was excellent, could have stayed all day. First winery - out of touch with the vineyard, pretty industrial, great food, great sommelier, wines ok. Great 20yo balsamic vinegar Second winery - fabulous vistas, facilities relate to the vineyards and cellars, wines below average. Behind time now, so rushed visit to Montalcino. Worth the visit for the views.

We had a fantastic day with tour driver Fabio who exceeded our expectations with great commentary & stopping for photos. Fully recommend this Day trip.

We had a great driver, and a great group. Scenery was the best for me. I thought the first winery was disorganized, didn’t know was having lunch etc. those of who did not order lunch the snack was terrible. Bout in all a good day.

The tuscan country side is amazing! It should be on every bucket list...Our guide David was great...it would be 5 stars but our pi kup point was changed without a text which led to a very stressful morning. But once we were able to get to the new point our day tour was wonderful.

As this tour was a small group, we found it friendly and we enjoyed lots of banter and laughs. The tour guide was informative and helpful.

The wine tasting at Poggio Ai Laghi was a very high-end experience. Great food, wine and information.

We loved going to San Gimignano and having free time there. The lunch at the winery was awesome!! The valleys were beautiful!

It was a terrific experience - a great day exploring parts of Tuscany with our driver and guide Ganti and four other co-travelers. The morning stop at St. Gimignano was enjoyable though a little long because we got there early. Lunch at the winery was the highlight of the day - a fabulous private room among the barrels and bottles with our own guide Bledard who gave us a terrific wine experience with wonderful Chiantis. The food was great too. Then, we visited another winery that showcased the Rosso and Brunello Montalcinos - walked down to the underground cellar which was very cool and then tasted wines with bread and olive oil and vinegar. Our last stop was the town of Montalcino - lovely fort and a nice brief visit before heading home. Our driver and guide was friendly, knowledgeable and very accommodating. The only drawback was the minivan - in the first one the a/c wasn’t working so we switched cars - the a/c was fine in the second one but the sliding door stopped functioning - the vans rattled a lot too - the company might be well advised to service their cars better or invest in new ones! Just a great way to see Tuscany - would highly recommend it - am sure the experience varies by driver/guide and by location visited - for us both were outstanding!

A well planned tour. We arrived San Gimignano before the crowds, then a very nice wine tasting lunch at a Chianti winery, followed by 2nd wine tasting at a secluded Montalcino winery, and finally strolling in Montalcino old town before the sunset with beautiful Tuscany scenery along the way-a truly enjoyable and memorable day. Special thanks to our guide Genty who is friendly and an amazing problem solver. Highly recommend this tour!

We were very disappointed. The full-day tour was cancelled for low attendance. We were offer a very low partial refund for one less winery and no lunch. Replacement sent us to two wineries with very small tasting amounts and no food. Staff seemed preoccupied, so all the participants just chatted. Montalcino was basically closed -we were taken there during afternoon siesta time. All the tour participants were starving and thirsty. Would have been happier if tour was just cancelled.

Hello, First the tour operator cancelled the tour just before the tour date. We went to Montalcino instead of this tour due to the technical problems. Montalcino tour was not well organized unfortunately. We visited 2 wineries for wine tasting however we only drank 1 glass wine in total. And the appretives were very poor. Only bread and olive oil were served. Additionaly, we were left in Montalcino village during siesta time and we could not visit any market or taste or drink coffee. We just could walk its street under the rain.

We are three Australians who enjoy wine and food experiences. The full day tour met all of our expectations, plus more. The tour guide was knowledgeable and enthusiastic and recognised our goals for the trip and ensured they were met. His commentary on the history, people, good and wine heritage and offerings were comprehensive and interesting. No question was too challenging for him. The wineries visited (Chianti - Casale Dello Sparviero and Montalcino - Podere Le Ripi) offered excellent ranges of wines to taste and good. The staff were enthusiastic and looked after us. The villages we visited along the way were fascinating and the guide provided insights and directions on where to go and what to look out for. A great day - very memorable which was enhanced by our guide.

Wonderful trip into the countryside. Beautiful wineries and a glimpse of the Tuscan countryside. Guide was very knowledgeable and friendly. The lunch was delicious. Would recommend this tour for those staying for a shorter visit in Siena.

This was an unbelievable trip! Everything we saw was just breathtaking. The views were spectacular. We had a lot of free time to roam around and see each part. Th guide was very accommodating and even shifted few things to ensure we get the best views before the sun went down.

The tour was excellent, San Gimignano was beautiful, the wine tastings were good and the commentary was informative. Several stops were in picturesque places and we had enough time to wander about the two towns. Altogether enjoyable!

Enjoyed being part of a small tour group. The lunch was good. Found the tour leader hard to hear and understand. Was a lot of driving involved. Would prefer less driving and more sight seeing.

Daniel our guide and driver was knowledgeable and kind. He allowed us free time after interesting discussions regarding the area. Highly recommend this tour!

We had a fantastic day, met some great people and enjoyed some lovely wine! Vincenzo was a fantastic guide and spoke fluent English. The trip to San Gimignano was early in the day, so we had the place to ourselves (before the hoards arrived). The town is beautiful and the views from the high walls were stunning - especially as the low cloud produced some atmosphere to our photos. The two vineyards were informative and interesting - providing the opportunity to purchase, but without any pressure. Lunch was good too. Cheese, meats and bread to start. Pasta dish with ragu to follow. With wine to compliment (including a bottle of Prosecco, kindly purchased by one of our party). A visit to Montalcino added to the experience - another medieval town with some beautiful architecture. We both had a wonderful day!